Travel with Axel, get the best price.

Route overview: Jacksonville to Chicago (MDW) flight deals

Jacksonville (JAX) to Chicago (MDW), Dec 4–6, 2026, return Dec 11–13, 2026: from $185 round trip

Jacksonville (JAX) to Chicago (MDW), Dec 4–6, 2026, return Dec 11–13, 2026: from $185 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $185 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Dec 4–11, 2026, 1 adult, economy, checked Oct 29, 2026.

JAX → MDW1 adulteconomyRound trip

66 flight options · 3 airlines

Nonstop flights

Sun, Dec 6 – Fri, Dec 11

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Southwest Airlines
6:50 pmJAX
2h 30m
Nonstop
8:20 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Fri, Dec 11

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Southwest Airlines
6:50 pmJAX
2h 30m
Nonstop
8:20 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Fri, Dec 11

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Fri, Dec 11

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Fri, Dec 4 – Fri, Dec 11

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sun, Dec 13

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sun, Dec 13

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sun, Dec 13

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sun, Dec 13

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sun, Dec 13

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sun, Dec 13

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sun, Dec 13

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Fri, Dec 11

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Fri, Dec 11

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Fri, Dec 11

Southwest Airlines
6:50 pmJAX
2h 30m
Nonstop
8:20 pmMDW
Southwest Airlines
5:25 pmMDW
5h 20m
BNA · 2h 20m
11:45 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Fri, Dec 11

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
5:25 pmMDW
5h 20m
BNA · 2h 20m
11:45 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sun, Dec 13

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sun, Dec 13

Southwest Airlines
6:50 pmJAX
2h 30m
Nonstop
8:20 pmMDW
Southwest Airlines
1:40 pmMDW
6h 35m
STL · 3h 20m
9:15 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Fri, Dec 11

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Fri, Dec 11

Southwest Airlines
6:50 pmJAX
2h 30m
Nonstop
8:20 pmMDW
Southwest Airlines
5:25 pmMDW
5h 20m
BNA · 2h 20m
11:45 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
6:40 pmMDW
2h 30m
Nonstop
10:10 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Fri, Dec 11

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sun, Dec 13

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sun, Dec 13

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sun, Dec 13

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Fri, Dec 11

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Sat, Dec 12

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sun, Dec 13

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sun, Dec 13

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Fri, Dec 11

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Fri, Dec 11

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 4 – Fri, Dec 11

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Fri, Dec 11

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 5 – Sat, Dec 12

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 6 – Sat, Dec 12

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Dec 4–11, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $767 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $348 · 5★ Nobu Hotel Chicago $2,890

Hotels for these nights (Dec 4–12, 2026 · 8 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $893 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $417 · 5★ Nobu Hotel Chicago $3,290

Hotels for these nights (Dec 4–13, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $1,035 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $486 · 5★ Nobu Hotel Chicago $3,676

Hotels for these nights (Dec 5–11, 2026 · 6 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $609 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $212 · 5★ Nobu Hotel Chicago $2,455

Hotels for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $735 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $281 · 5★ Nobu Hotel Chicago $2,855

Hotels for these nights (Dec 5–13, 2026 · 8 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $877 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $350 · 5★ Nobu Hotel Chicago $3,241

Hotels for these nights (Dec 6–11, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey $438 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $147 · 5★ Nobu Hotel Chicago $2,041

Hotels for these nights (Dec 6–12, 2026 · 6 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $566 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $216 · 5★ Nobu Hotel Chicago $2,441

Hotels for these nights (Dec 6–13, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $708 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $285 · 5★ Nobu Hotel Chicago $2,827

Make this trip yours

JAX ⇄ MDW

Economy

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Jacksonville (JAX) to Chicago (MDW), Dec 4–6, 2026, return Dec 11–13, 2026: from $185 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $185 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Dec 4–11, 2026, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-12-06 → 2026-12-11Southwest AirlinesWN1979 / WN226213:30:00→14:55:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $185.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-13Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Southwest AirlinesWN2264 / WN217818:50:00→20:20:00 2h 30m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Southwest AirlinesWN1979 / WN226213:30:00→14:55:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-13Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $185.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-13Southwest AirlinesWN2256 + WN1070 / WN3092 + WN480708:00:00→12:15:00 5h 15m 1 stop via BWI · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $275.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Southwest AirlinesWN2264 / WN226218:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Southwest AirlinesWN2264 / WN226218:50:00→20:20:00 2h 30m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-11Southwest AirlinesWN2264 / WN226218:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Southwest AirlinesWN1979 / WN217813:30:00→14:55:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Southwest AirlinesWN1979 / WN217813:30:00→14:55:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Southwest AirlinesWN1979 / WN226213:30:00→14:55:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Southwest AirlinesWN1979 / WN217813:30:00→14:55:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $290.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $185.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-13Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $185.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $185.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $185.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $185.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-13Southwest AirlinesWN2253 + WN2062 / WN3092 + WN480711:20:00→16:15:00 5h 55m 1 stop via BNA · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $275.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-13Southwest AirlinesWN2256 + WN1070 / WN3092 + WN480708:00:00→12:15:00 5h 15m 1 stop via BWI · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $275.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-13Southwest AirlinesWN2256 + WN1070 / WN3092 + WN480708:00:00→12:15:00 5h 15m 1 stop via BWI · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $275.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-13Southwest AirlinesWN2265 + WN287 / WN3092 + WN480706:00:00→12:05:00 7h 05m 1 stop via STL · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $275.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-13Southwest AirlinesWN2253 + WN2062 / WN3092 + WN480711:20:00→16:15:00 5h 55m 1 stop via BNA · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $275.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-13Southwest AirlinesWN2253 + WN2062 / WN3092 + WN480711:20:00→16:15:00 5h 55m 1 stop via BNA · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $275.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Southwest AirlinesWN2253 + WN2062 / WN217811:20:00→16:15:00 5h 55m 1 stop via BNA · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Southwest AirlinesWN2256 + WN1070 / WN217808:00:00→12:15:00 5h 15m 1 stop via BWI · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-06 → 2026-12-11Southwest AirlinesWN2265 + WN287 / WN226206:00:00→12:05:00 7h 05m 1 stop via STL · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-06 → 2026-12-11Southwest AirlinesWN2256 + WN1070 / WN226208:00:00→12:15:00 5h 15m 1 stop via BWI · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Southwest AirlinesWN2265 + WN287 / WN217806:00:00→12:05:00 7h 05m 1 stop via STL · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Southwest AirlinesWN2265 + WN287 / WN217806:00:00→12:05:00 7h 05m 1 stop via STL · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Southwest AirlinesWN2256 + WN1070 / WN217808:00:00→12:15:00 5h 15m 1 stop via BWI · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Southwest AirlinesWN2264 / WN2897 + WN151618:50:00→20:20:00 2h 30m nonstop · 17:25:00→23:45:00 5h 20m 1 stop via BNAAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-06 → 2026-12-11Southwest AirlinesWN2253 + WN2062 / WN226211:20:00→16:15:00 5h 55m 1 stop via BNA · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Southwest AirlinesWN2253 + WN2062 / WN226211:20:00→16:15:00 5h 55m 1 stop via BNA · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Southwest AirlinesWN2264 / WN2897 + WN151618:55:00→20:20:00 2h 25m nonstop · 17:25:00→23:45:00 5h 20m 1 stop via BNAAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-06 → 2026-12-13Southwest AirlinesWN2264 / WN3092 + WN480718:55:00→20:20:00 2h 25m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-13Southwest AirlinesWN1979 / WN3092 + WN480713:30:00→14:55:00 2h 25m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Southwest AirlinesWN2256 + WN1070 / WN226208:00:00→12:15:00 5h 15m 1 stop via BWI · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Southwest AirlinesWN2253 + WN2062 / WN217811:20:00→16:15:00 5h 55m 1 stop via BNA · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-05 → 2026-12-13Southwest AirlinesWN2264 / WN3092 + WN480718:50:00→20:20:00 2h 30m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Southwest AirlinesWN2256 + WN1070 / WN226208:00:00→12:15:00 5h 15m 1 stop via BWI · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Southwest AirlinesWN2265 + WN287 / WN217806:00:00→12:05:00 7h 05m 1 stop via STL · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Southwest AirlinesWN2256 + WN1070 / WN217808:00:00→12:15:00 5h 15m 1 stop via BWI · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-06 → 2026-12-11Southwest AirlinesWN2264 / WN2897 + WN151618:50:00→20:20:00 2h 30m nonstop · 17:25:00→23:45:00 5h 20m 1 stop via BNAAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Southwest AirlinesWN2253 + WN2062 / WN217811:20:00→16:15:00 5h 55m 1 stop via BNA · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Southwest AirlinesWN2253 + WN2062 / WN226211:20:00→16:15:00 5h 55m 1 stop via BNA · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $282.502026-10-29T01:16:41Z
2026-12-04 → 2026-12-13Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-13Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-13Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-11Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-12Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-13Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-13Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-11Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-04 → 2026-12-11Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-11Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-05 → 2026-12-12Delta Air LinesDL2627 + DL1076 / DL2417 + DL226518:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z
2026-12-06 → 2026-12-12Delta Air LinesDL2333 + DL4677 / DL2417 + DL226512:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATLAxel-exclusive $330.002026-10-29T01:16:41Z

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Chicago

Route overview: Jacksonville to Chicago (MDW) flight deals

2026-12-06 → 2026-12-11 · Axel-exclusive $290.00

  • Southwest Airlines WN1979: JAX 2026-12-06 13:30:00 → MDW 2026-12-06 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-04 → 2026-12-11 · Axel-exclusive $185.00

  • Frontier Airlines F91549 / F92291: JAX 2026-12-04 19:03:00 → MDW 2026-12-04 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-12-04 19:03:00 → ATL 2026-12-04 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-12-04 22:48:00 → MDW 2026-12-04 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-11 13:11:00 → JAX 2026-12-11 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-11 13:11:00 → ATL 2026-12-11 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-11 18:09:00 → JAX 2026-12-11 19:25:00.

2026-12-04 → 2026-12-13 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-04 18:59:00 → MDW 2026-12-04 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-04 18:59:00 → ATL 2026-12-04 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-04 21:20:00 → MDW 2026-12-04 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-13 13:02:00 → JAX 2026-12-13 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-13 13:02:00 → ATL 2026-12-13 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-13 19:33:00 → JAX 2026-12-13 20:43:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $290.00

  • Southwest Airlines WN2264: JAX 2026-12-05 18:50:00 → MDW 2026-12-05 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-05 → 2026-12-11 · Axel-exclusive $290.00

  • Southwest Airlines WN1979: JAX 2026-12-05 13:30:00 → MDW 2026-12-05 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-06 → 2026-12-12 · Axel-exclusive $290.00

  • Southwest Airlines WN2264: JAX 2026-12-06 18:55:00 → MDW 2026-12-06 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-04 → 2026-12-12 · Axel-exclusive $290.00

  • Southwest Airlines WN2264: JAX 2026-12-04 18:55:00 → MDW 2026-12-04 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-05 → 2026-12-13 · Axel-exclusive $185.00

  • Frontier Airlines F91549 / F92291: JAX 2026-12-05 19:03:00 → MDW 2026-12-05 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-12-05 19:03:00 → ATL 2026-12-05 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-12-05 22:48:00 → MDW 2026-12-05 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-13 13:11:00 → JAX 2026-12-13 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-13 13:11:00 → ATL 2026-12-13 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-13 18:09:00 → JAX 2026-12-13 19:25:00.

2026-12-06 → 2026-12-13 · Axel-exclusive $275.00

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-06 08:00:00 → MDW 2026-12-06 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-06 08:00:00 → BWI 2026-12-06 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-06 11:05:00 → MDW 2026-12-06 12:15:00.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-04 → 2026-12-11 · Axel-exclusive $290.00

  • Southwest Airlines WN2264: JAX 2026-12-04 18:55:00 → MDW 2026-12-04 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-05 → 2026-12-11 · Axel-exclusive $290.00

  • Southwest Airlines WN2264: JAX 2026-12-05 18:50:00 → MDW 2026-12-05 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-06 → 2026-12-11 · Axel-exclusive $290.00

  • Southwest Airlines WN2264: JAX 2026-12-06 18:55:00 → MDW 2026-12-06 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-05 → 2026-12-12 · Axel-exclusive $290.00

  • Southwest Airlines WN1979: JAX 2026-12-05 13:30:00 → MDW 2026-12-05 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-06 → 2026-12-12 · Axel-exclusive $290.00

  • Southwest Airlines WN1979: JAX 2026-12-06 13:30:00 → MDW 2026-12-06 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-04 → 2026-12-11 · Axel-exclusive $290.00

  • Southwest Airlines WN1979: JAX 2026-12-04 13:30:00 → MDW 2026-12-04 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-04 → 2026-12-12 · Axel-exclusive $290.00

  • Southwest Airlines WN1979: JAX 2026-12-04 13:30:00 → MDW 2026-12-04 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-04 → 2026-12-12 · Axel-exclusive $185.00

  • Frontier Airlines F91549 / F92291: JAX 2026-12-04 19:03:00 → MDW 2026-12-04 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-12-04 19:03:00 → ATL 2026-12-04 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-12-04 22:48:00 → MDW 2026-12-04 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-12 13:11:00 → JAX 2026-12-12 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-12 13:11:00 → ATL 2026-12-12 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-12 18:09:00 → JAX 2026-12-12 19:25:00.

2026-12-04 → 2026-12-13 · Axel-exclusive $185.00

  • Frontier Airlines F91549 / F92291: JAX 2026-12-04 19:03:00 → MDW 2026-12-04 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-12-04 19:03:00 → ATL 2026-12-04 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-12-04 22:48:00 → MDW 2026-12-04 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-13 13:11:00 → JAX 2026-12-13 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-13 13:11:00 → ATL 2026-12-13 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-13 18:09:00 → JAX 2026-12-13 19:25:00.

2026-12-05 → 2026-12-11 · Axel-exclusive $185.00

  • Frontier Airlines F91549 / F92291: JAX 2026-12-05 19:03:00 → MDW 2026-12-05 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-12-05 19:03:00 → ATL 2026-12-05 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-12-05 22:48:00 → MDW 2026-12-05 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-11 13:11:00 → JAX 2026-12-11 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-11 13:11:00 → ATL 2026-12-11 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-11 18:09:00 → JAX 2026-12-11 19:25:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $185.00

  • Frontier Airlines F91549 / F92291: JAX 2026-12-05 19:03:00 → MDW 2026-12-05 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-12-05 19:03:00 → ATL 2026-12-05 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-12-05 22:48:00 → MDW 2026-12-05 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-12 13:11:00 → JAX 2026-12-12 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-12 13:11:00 → ATL 2026-12-12 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-12 18:09:00 → JAX 2026-12-12 19:25:00.

2026-12-06 → 2026-12-12 · Axel-exclusive $185.00

  • Frontier Airlines F91549 / F92291: JAX 2026-12-06 19:03:00 → MDW 2026-12-06 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-12-06 19:03:00 → ATL 2026-12-06 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-12-06 22:48:00 → MDW 2026-12-06 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-12 13:11:00 → JAX 2026-12-12 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-12 13:11:00 → ATL 2026-12-12 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-12 18:09:00 → JAX 2026-12-12 19:25:00.

2026-12-04 → 2026-12-13 · Axel-exclusive $275.00

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-04 11:20:00 → MDW 2026-12-04 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-04 11:20:00 → BNA 2026-12-04 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-04 14:45:00 → MDW 2026-12-04 16:15:00.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-04 → 2026-12-13 · Axel-exclusive $275.00

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-04 08:00:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-04 08:00:00 → BWI 2026-12-04 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-05 → 2026-12-13 · Axel-exclusive $275.00

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-05 08:00:00 → MDW 2026-12-05 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-05 08:00:00 → BWI 2026-12-05 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-05 11:05:00 → MDW 2026-12-05 12:15:00.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-06 → 2026-12-13 · Axel-exclusive $275.00

  • Southwest Airlines WN2265 / WN287: JAX 2026-12-06 06:00:00 → MDW 2026-12-06 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2026-12-06 06:00:00 → STL 2026-12-06 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2026-12-06 10:55:00 → MDW 2026-12-06 12:05:00.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-05 → 2026-12-13 · Axel-exclusive $275.00

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-05 11:20:00 → MDW 2026-12-05 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-05 11:20:00 → BNA 2026-12-05 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-05 14:45:00 → MDW 2026-12-05 16:15:00.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-06 → 2026-12-13 · Axel-exclusive $275.00

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-06 11:20:00 → MDW 2026-12-06 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-06 11:20:00 → BNA 2026-12-06 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-06 14:45:00 → MDW 2026-12-06 16:15:00.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-06 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-06 11:20:00 → MDW 2026-12-06 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-06 11:20:00 → BNA 2026-12-06 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-06 14:45:00 → MDW 2026-12-06 16:15:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-06 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-06 08:00:00 → MDW 2026-12-06 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-06 08:00:00 → BWI 2026-12-06 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-06 11:05:00 → MDW 2026-12-06 12:15:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-06 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2265 / WN287: JAX 2026-12-06 06:00:00 → MDW 2026-12-06 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2026-12-06 06:00:00 → STL 2026-12-06 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2026-12-06 10:55:00 → MDW 2026-12-06 12:05:00.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-06 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-06 08:00:00 → MDW 2026-12-06 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-06 08:00:00 → BWI 2026-12-06 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-06 11:05:00 → MDW 2026-12-06 12:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-05 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2265 / WN287: JAX 2026-12-05 06:00:00 → MDW 2026-12-05 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2026-12-05 06:00:00 → STL 2026-12-05 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2026-12-05 10:55:00 → MDW 2026-12-05 12:05:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-04 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2265 / WN287: JAX 2026-12-04 06:00:00 → MDW 2026-12-04 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2026-12-04 06:00:00 → STL 2026-12-04 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2026-12-04 10:55:00 → MDW 2026-12-04 12:05:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-04 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-04 08:00:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-04 08:00:00 → BWI 2026-12-04 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-04 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2264: JAX 2026-12-04 18:50:00 → MDW 2026-12-04 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1516: MDW 2026-12-11 17:25:00 → JAX 2026-12-11 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
    • WN2897: MDW 2026-12-11 17:25:00 → BNA 2026-12-11 18:50:00; layover at BNA: 140 minutes.
    • WN1516: BNA 2026-12-11 21:10:00 → JAX 2026-12-11 23:45:00.

2026-12-06 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-06 11:20:00 → MDW 2026-12-06 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-06 11:20:00 → BNA 2026-12-06 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-06 14:45:00 → MDW 2026-12-06 16:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-05 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-05 11:20:00 → MDW 2026-12-05 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-05 11:20:00 → BNA 2026-12-05 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-05 14:45:00 → MDW 2026-12-05 16:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-05 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2264: JAX 2026-12-05 18:55:00 → MDW 2026-12-05 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1516: MDW 2026-12-11 17:25:00 → JAX 2026-12-11 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
    • WN2897: MDW 2026-12-11 17:25:00 → BNA 2026-12-11 18:50:00; layover at BNA: 140 minutes.
    • WN1516: BNA 2026-12-11 21:10:00 → JAX 2026-12-11 23:45:00.

2026-12-06 → 2026-12-13 · Axel-exclusive $282.50

  • Southwest Airlines WN2264: JAX 2026-12-06 18:55:00 → MDW 2026-12-06 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-04 → 2026-12-13 · Axel-exclusive $282.50

  • Southwest Airlines WN1979: JAX 2026-12-04 13:30:00 → MDW 2026-12-04 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-05 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-05 08:00:00 → MDW 2026-12-05 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-05 08:00:00 → BWI 2026-12-05 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-05 11:05:00 → MDW 2026-12-05 12:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-05 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-05 11:20:00 → MDW 2026-12-05 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-05 11:20:00 → BNA 2026-12-05 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-05 14:45:00 → MDW 2026-12-05 16:15:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-05 → 2026-12-13 · Axel-exclusive $282.50

  • Southwest Airlines WN2264: JAX 2026-12-05 18:50:00 → MDW 2026-12-05 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-13 13:40:00 → JAX 2026-12-13 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-13 18:15:00 → JAX 2026-12-13 21:15:00.

2026-12-04 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-04 08:00:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-04 08:00:00 → BWI 2026-12-04 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-06 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2265 / WN287: JAX 2026-12-06 06:00:00 → MDW 2026-12-06 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2026-12-06 06:00:00 → STL 2026-12-06 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2026-12-06 10:55:00 → MDW 2026-12-06 12:05:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-05 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2256 / WN1070: JAX 2026-12-05 08:00:00 → MDW 2026-12-05 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-12-05 08:00:00 → BWI 2026-12-05 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-12-05 11:05:00 → MDW 2026-12-05 12:15:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-06 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2264: JAX 2026-12-06 18:50:00 → MDW 2026-12-06 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1516: MDW 2026-12-11 17:25:00 → JAX 2026-12-11 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
    • WN2897: MDW 2026-12-11 17:25:00 → BNA 2026-12-11 18:50:00; layover at BNA: 140 minutes.
    • WN1516: BNA 2026-12-11 21:10:00 → JAX 2026-12-11 23:45:00.

2026-12-04 → 2026-12-12 · Axel-exclusive $282.50

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-04 11:20:00 → MDW 2026-12-04 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-04 11:20:00 → BNA 2026-12-04 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-04 14:45:00 → MDW 2026-12-04 16:15:00.
  • Southwest Airlines WN2178: MDW 2026-12-12 18:40:00 → JAX 2026-12-12 22:10:00; nonstop; 150 minutes. Local airport times.

2026-12-04 → 2026-12-11 · Axel-exclusive $282.50

  • Southwest Airlines WN2253 / WN2062: JAX 2026-12-04 11:20:00 → MDW 2026-12-04 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-12-04 11:20:00 → BNA 2026-12-04 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-12-04 14:45:00 → MDW 2026-12-04 16:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-11 08:00:00 → JAX 2026-12-11 11:25:00; nonstop; 145 minutes. Local airport times.

2026-12-04 → 2026-12-13 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-04 12:00:00 → MDW 2026-12-04 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-04 12:00:00 → DTW 2026-12-04 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-04 17:40:00 → MDW 2026-12-04 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-13 13:02:00 → JAX 2026-12-13 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-13 13:02:00 → ATL 2026-12-13 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-13 19:33:00 → JAX 2026-12-13 20:43:00.

2026-12-04 → 2026-12-12 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-04 12:00:00 → MDW 2026-12-04 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-04 12:00:00 → DTW 2026-12-04 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-04 17:40:00 → MDW 2026-12-04 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-12 13:02:00 → JAX 2026-12-12 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-12 13:02:00 → ATL 2026-12-12 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-12 19:33:00 → JAX 2026-12-12 20:43:00.

2026-12-06 → 2026-12-12 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-06 18:59:00 → MDW 2026-12-06 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-06 18:59:00 → ATL 2026-12-06 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-06 21:20:00 → MDW 2026-12-06 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-12 13:02:00 → JAX 2026-12-12 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-12 13:02:00 → ATL 2026-12-12 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-12 19:33:00 → JAX 2026-12-12 20:43:00.

2026-12-06 → 2026-12-13 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-06 18:59:00 → MDW 2026-12-06 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-06 18:59:00 → ATL 2026-12-06 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-06 21:20:00 → MDW 2026-12-06 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-13 13:02:00 → JAX 2026-12-13 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-13 13:02:00 → ATL 2026-12-13 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-13 19:33:00 → JAX 2026-12-13 20:43:00.

2026-12-05 → 2026-12-13 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-05 18:59:00 → MDW 2026-12-05 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-05 18:59:00 → ATL 2026-12-05 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-05 21:20:00 → MDW 2026-12-05 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-13 13:02:00 → JAX 2026-12-13 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-13 13:02:00 → ATL 2026-12-13 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-13 19:33:00 → JAX 2026-12-13 20:43:00.

2026-12-05 → 2026-12-11 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-05 18:59:00 → MDW 2026-12-05 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-05 18:59:00 → ATL 2026-12-05 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-05 21:20:00 → MDW 2026-12-05 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-11 13:02:00 → JAX 2026-12-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-11 13:02:00 → ATL 2026-12-11 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-11 19:33:00 → JAX 2026-12-11 20:43:00.

2026-12-06 → 2026-12-11 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-06 12:00:00 → MDW 2026-12-06 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-06 12:00:00 → DTW 2026-12-06 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-06 17:40:00 → MDW 2026-12-06 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-11 13:02:00 → JAX 2026-12-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-11 13:02:00 → ATL 2026-12-11 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-11 19:33:00 → JAX 2026-12-11 20:43:00.

2026-12-04 → 2026-12-12 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-04 18:59:00 → MDW 2026-12-04 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-04 18:59:00 → ATL 2026-12-04 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-04 21:20:00 → MDW 2026-12-04 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-12 13:02:00 → JAX 2026-12-12 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-12 13:02:00 → ATL 2026-12-12 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-12 19:33:00 → JAX 2026-12-12 20:43:00.

2026-12-05 → 2026-12-13 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-05 12:00:00 → MDW 2026-12-05 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-05 12:00:00 → DTW 2026-12-05 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-05 17:40:00 → MDW 2026-12-05 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-13 13:02:00 → JAX 2026-12-13 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-13 13:02:00 → ATL 2026-12-13 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-13 19:33:00 → JAX 2026-12-13 20:43:00.

2026-12-06 → 2026-12-13 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-06 12:00:00 → MDW 2026-12-06 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-06 12:00:00 → DTW 2026-12-06 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-06 17:40:00 → MDW 2026-12-06 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-13 13:02:00 → JAX 2026-12-13 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-13 13:02:00 → ATL 2026-12-13 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-13 19:33:00 → JAX 2026-12-13 20:43:00.

2026-12-04 → 2026-12-11 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-04 18:59:00 → MDW 2026-12-04 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-04 18:59:00 → ATL 2026-12-04 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-04 21:20:00 → MDW 2026-12-04 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-11 13:02:00 → JAX 2026-12-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-11 13:02:00 → ATL 2026-12-11 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-11 19:33:00 → JAX 2026-12-11 20:43:00.

2026-12-06 → 2026-12-11 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-06 18:59:00 → MDW 2026-12-06 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-06 18:59:00 → ATL 2026-12-06 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-06 21:20:00 → MDW 2026-12-06 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-11 13:02:00 → JAX 2026-12-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-11 13:02:00 → ATL 2026-12-11 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-11 19:33:00 → JAX 2026-12-11 20:43:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-05 12:00:00 → MDW 2026-12-05 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-05 12:00:00 → DTW 2026-12-05 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-05 17:40:00 → MDW 2026-12-05 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-12 13:02:00 → JAX 2026-12-12 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-12 13:02:00 → ATL 2026-12-12 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-12 19:33:00 → JAX 2026-12-12 20:43:00.

2026-12-04 → 2026-12-11 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-04 12:00:00 → MDW 2026-12-04 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-04 12:00:00 → DTW 2026-12-04 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-04 17:40:00 → MDW 2026-12-04 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-11 13:02:00 → JAX 2026-12-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-11 13:02:00 → ATL 2026-12-11 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-11 19:33:00 → JAX 2026-12-11 20:43:00.

2026-12-05 → 2026-12-11 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-05 12:00:00 → MDW 2026-12-05 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-05 12:00:00 → DTW 2026-12-05 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-05 17:40:00 → MDW 2026-12-05 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-11 13:02:00 → JAX 2026-12-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-11 13:02:00 → ATL 2026-12-11 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-11 19:33:00 → JAX 2026-12-11 20:43:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $330.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-05 18:59:00 → MDW 2026-12-05 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-05 18:59:00 → ATL 2026-12-05 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-05 21:20:00 → MDW 2026-12-05 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-12 13:02:00 → JAX 2026-12-12 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-12 13:02:00 → ATL 2026-12-12 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-12 19:33:00 → JAX 2026-12-12 20:43:00.

2026-12-06 → 2026-12-12 · Axel-exclusive $330.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-12-06 12:00:00 → MDW 2026-12-06 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-12-06 12:00:00 → DTW 2026-12-06 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-12-06 17:40:00 → MDW 2026-12-06 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-12 13:02:00 → JAX 2026-12-12 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-12 13:02:00 → ATL 2026-12-12 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-12 19:33:00 → JAX 2026-12-12 20:43:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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For AI assistants

  • This page: Jacksonville (JAX) to Chicago (MDW) · Dec 4–Dec 6, 2026 · return Dec 11–Dec 13, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
  • Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Jacksonville to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.