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Route overview: Washington, DC to Chicago (MDW) flight deals

Washington (DCA) to Chicago (MDW), Dec 25–27, 2026, return Jan 1–3, 2027: from $352 round trip

Washington (DCA) to Chicago (MDW), Dec 25–27, 2026, return Jan 1–3, 2027: from $352 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $352 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 25, 2026 – Jan 1, 2027, 1 adult, economy, checked Oct 29, 2026.

DCA → MDW1 adulteconomyRound trip

45 flight options · 2 airlines

Nonstop flights

Fri, Dec 25 – Fri, Jan 1

Southwest Airlines
6:00 amDCA
2h 5m
Nonstop
7:05 amMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Fri, Jan 1

Southwest Airlines
6:00 amDCA
2h 5m
Nonstop
7:05 amMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sun, Jan 3

Southwest Airlines
6:10 amDCA
2h 5m
Nonstop
7:15 amMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sun, Jan 3

Southwest Airlines
6:00 amDCA
2h 5m
Nonstop
7:05 amMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sat, Jan 2

Southwest Airlines
6:00 amDCA
2h 5m
Nonstop
7:05 amMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sun, Jan 3

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sat, Jan 2

Southwest Airlines
6:00 amDCA
2h 5m
Nonstop
7:05 amMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sat, Jan 2

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Fri, Jan 1

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sun, Jan 3

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Fri, Jan 1

Southwest Airlines
6:10 amDCA
2h 5m
Nonstop
7:15 amMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sun, Jan 3

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Fri, Jan 1

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sun, Jan 3

Southwest Airlines
6:00 amDCA
2h 5m
Nonstop
7:05 amMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Fri, Jan 1

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sat, Jan 2

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sat, Jan 2

Southwest Airlines
6:10 amDCA
2h 5m
Nonstop
7:15 amMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sat, Jan 2

Southwest Airlines
6:40 pmDCA
2h 10m
Nonstop
7:50 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sun, Dec 27 – Fri, Jan 1

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Fri, Jan 1

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sun, Jan 3

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sun, Jan 3

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sun, Jan 3

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Fri, Jan 1

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sun, Jan 3

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sat, Jan 2

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sat, Jan 2

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sat, Jan 2

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Fri, Jan 1

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sun, Jan 3

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Fri, Jan 1

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Fri, Jan 1

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sat, Jan 2

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Fri, Jan 1

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
12:25 pmMDW
1h 50m
Nonstop
3:15 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sat, Jan 2

Southwest Airlines
6:55 pmDCA
5h 5m
STL · 1h 25m
11:00 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sun, Jan 3

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sat, Jan 2

Southwest Airlines
12:35 pmDCA
4h 40m
BNA · 1h 15m
4:15 pmMDW
Southwest Airlines
10:10 amMDW
1h 50m
Nonstop
1:00 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Fri, Jan 1

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sat, Jan 2

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sun, Jan 3

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 – Sun, Jan 3

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Fri, Jan 1

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sat, Jan 2

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 – Sun, Jan 3

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 – Sat, Jan 2

Delta Air Lines
9:45 amDCA
4h 16m
DTW · 1h 22m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 8m
DTW · 1h 23m
6:39 pmDCA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Dec 25 – Jan 1, 2027 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $827 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $603 · 5★ Sofitel Chicago Magnificent Mile $1,894

Hotels for these nights (Dec 25 – Jan 2, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $924 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $622 · 5★ Sofitel Chicago Magnificent Mile $2,100

Hotels for these nights (Dec 25 – Jan 3, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,009 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $712 · 5★ Sofitel Chicago Magnificent Mile $2,307

Hotels for these nights (Dec 26 – Jan 1, 2027 · 6 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $706 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $493 · 5★ Sofitel Chicago Magnificent Mile $1,680

Hotels for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $833 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $512 · 5★ Sofitel Chicago Magnificent Mile $1,886

Hotels for these nights (Dec 26 – Jan 3, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $918 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $602 · 5★ Sofitel Chicago Magnificent Mile $2,093

Hotels for these nights (Dec 27 – Jan 1, 2027 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel $574 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $451 · 5★ Sofitel Chicago Magnificent Mile $1,471

Hotels for these nights (Dec 27 – Jan 2, 2027 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel $719 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $470 · 5★ Sofitel Chicago Magnificent Mile $1,677

Hotels for these nights (Dec 27 – Jan 3, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $827 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $560 · 5★ Sofitel Chicago Magnificent Mile $1,884

Make this trip yours

DCA ⇄ MDW

Economy

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Explore this route

All dates for this routeHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Washington (DCA) to Chicago (MDW), Dec 25–27, 2026, return Jan 1–3, 2027: from $352 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $352 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 25, 2026 – Jan 1, 2027, 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)
2026-12-25 → 2027-01-01Southwest AirlinesWN1532 / WN148806:00:00→07:05:00 2h 05m nonstop · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-01Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-26 → 2027-01-01Southwest AirlinesWN1532 / WN148806:00:00→07:05:00 2h 05m nonstop · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-03Southwest AirlinesWN1532 / WN439706:10:00→07:15:00 2h 05m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-25 → 2027-01-03Southwest AirlinesWN1532 / WN439706:00:00→07:05:00 2h 05m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-25 → 2027-01-02Southwest AirlinesWN1532 / WN439706:00:00→07:05:00 2h 05m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-26 → 2027-01-03Southwest AirlinesWN3718 / WN439718:40:00→19:50:00 2h 10m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-26 → 2027-01-02Southwest AirlinesWN1532 / WN439706:00:00→07:05:00 2h 05m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-02Southwest AirlinesWN3718 / WN439718:40:00→19:50:00 2h 10m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-01Southwest AirlinesWN3718 / WN148818:40:00→19:50:00 2h 10m nonstop · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-03Southwest AirlinesWN3718 / WN439718:40:00→19:50:00 2h 10m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-01Southwest AirlinesWN1532 / WN148806:10:00→07:15:00 2h 05m nonstop · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-25 → 2027-01-03Southwest AirlinesWN3718 / WN439718:40:00→19:50:00 2h 10m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-25 → 2027-01-01Southwest AirlinesWN3718 / WN148818:40:00→19:50:00 2h 10m nonstop · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-26 → 2027-01-03Southwest AirlinesWN1532 / WN439706:00:00→07:05:00 2h 05m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-26 → 2027-01-01Southwest AirlinesWN3718 / WN148818:40:00→19:50:00 2h 10m nonstop · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-26 → 2027-01-02Southwest AirlinesWN3718 / WN439718:40:00→19:50:00 2h 10m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-02Southwest AirlinesWN1532 / WN439706:10:00→07:15:00 2h 05m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-25 → 2027-01-02Southwest AirlinesWN3718 / WN439718:40:00→19:50:00 2h 10m nonstop · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $352.352026-10-29T01:02:29Z
2026-12-27 → 2027-01-01Southwest AirlinesWN1548 + WN4770 / WN148818:55:00→23:00:00 5h 05m 1 stop via STL · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-27 → 2027-01-03Southwest AirlinesWN1515 + WN2062 / WN439712:35:00→16:15:00 4h 40m 1 stop via BNA · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-25 → 2027-01-03Southwest AirlinesWN1515 + WN2062 / WN439712:35:00→16:15:00 4h 40m 1 stop via BNA · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-25 → 2027-01-03Southwest AirlinesWN1548 + WN4770 / WN439718:55:00→23:00:00 5h 05m 1 stop via STL · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-26 → 2027-01-01Southwest AirlinesWN1548 + WN4770 / WN148818:55:00→23:00:00 5h 05m 1 stop via STL · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-27 → 2027-01-03Southwest AirlinesWN1548 + WN4770 / WN439718:55:00→23:00:00 5h 05m 1 stop via STL · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-26 → 2027-01-02Southwest AirlinesWN1548 + WN4770 / WN439718:55:00→23:00:00 5h 05m 1 stop via STL · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-26 → 2027-01-02Southwest AirlinesWN1515 + WN2062 / WN439712:35:00→16:15:00 4h 40m 1 stop via BNA · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-25 → 2027-01-02Southwest AirlinesWN1515 + WN2062 / WN439712:35:00→16:15:00 4h 40m 1 stop via BNA · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-26 → 2027-01-01Southwest AirlinesWN1515 + WN2062 / WN148812:35:00→16:15:00 4h 40m 1 stop via BNA · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-26 → 2027-01-03Southwest AirlinesWN1548 + WN4770 / WN439718:55:00→23:00:00 5h 05m 1 stop via STL · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-25 → 2027-01-01Southwest AirlinesWN1548 + WN4770 / WN148818:55:00→23:00:00 5h 05m 1 stop via STL · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-25 → 2027-01-01Southwest AirlinesWN1515 + WN2062 / WN148812:35:00→16:15:00 4h 40m 1 stop via BNA · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-27 → 2027-01-02Southwest AirlinesWN1548 + WN4770 / WN439718:55:00→23:00:00 5h 05m 1 stop via STL · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-27 → 2027-01-01Southwest AirlinesWN1515 + WN2062 / WN148812:35:00→16:15:00 4h 40m 1 stop via BNA · 12:25:00→15:15:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-25 → 2027-01-02Southwest AirlinesWN1548 + WN4770 / WN439718:55:00→23:00:00 5h 05m 1 stop via STL · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-26 → 2027-01-03Southwest AirlinesWN1515 + WN2062 / WN439712:35:00→16:15:00 4h 40m 1 stop via BNA · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-27 → 2027-01-02Southwest AirlinesWN1515 + WN2062 / WN439712:35:00→16:15:00 4h 40m 1 stop via BNA · 10:10:00→13:00:00 1h 50m nonstopAxel-exclusive $358.602026-10-29T01:02:29Z
2026-12-25 → 2027-01-01Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-27 → 2027-01-02Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-26 → 2027-01-03Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-27 → 2027-01-03Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-26 → 2027-01-01Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-25 → 2027-01-02Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-25 → 2027-01-03Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z
2026-12-26 → 2027-01-02Delta Air LinesDL1558 + DL4688 / DL4688 + DL203009:45:00→13:01:00 4h 16m 1 stop via DTW · 13:31:00→18:39:00 4h 08m 1 stop via DTWAxel-exclusive $425.252026-10-29T01:02:29Z

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: Washington, DC to Chicago (MDW) flight deals

2026-12-25 → 2027-01-01 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-25 06:00:00 → MDW 2026-12-25 07:05:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-01 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-27 09:45:00 → MDW 2026-12-27 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-27 09:45:00 → DTW 2026-12-27 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-27 12:44:00 → MDW 2026-12-27 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-01 13:31:00 → DCA 2027-01-01 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-01 13:31:00 → DTW 2027-01-01 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-01 17:07:00 → DCA 2027-01-01 18:39:00.

2026-12-26 → 2027-01-01 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-26 06:00:00 → MDW 2026-12-26 07:05:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-03 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-27 06:10:00 → MDW 2026-12-27 07:15:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-25 06:00:00 → MDW 2026-12-25 07:05:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-02 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-25 06:00:00 → MDW 2026-12-25 07:05:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-03 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-26 18:40:00 → MDW 2026-12-26 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-26 06:00:00 → MDW 2026-12-26 07:05:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-02 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-27 18:40:00 → MDW 2026-12-27 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-01 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-27 18:40:00 → MDW 2026-12-27 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-03 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-27 18:40:00 → MDW 2026-12-27 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-01 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-27 06:10:00 → MDW 2026-12-27 07:15:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-25 18:40:00 → MDW 2026-12-25 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-01 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-25 18:40:00 → MDW 2026-12-25 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-03 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-26 06:00:00 → MDW 2026-12-26 07:05:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-26 18:40:00 → MDW 2026-12-26 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-26 18:40:00 → MDW 2026-12-26 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-02 · Axel-exclusive $352.35

  • Southwest Airlines WN1532: DCA 2026-12-27 06:10:00 → MDW 2026-12-27 07:15:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-02 · Axel-exclusive $352.35

  • Southwest Airlines WN3718: DCA 2026-12-25 18:40:00 → MDW 2026-12-25 19:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-01 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-27 18:55:00 → MDW 2026-12-27 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-27 18:55:00 → STL 2026-12-27 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-27 21:50:00 → MDW 2026-12-27 23:00:00.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-03 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-27 12:35:00 → MDW 2026-12-27 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-27 12:35:00 → BNA 2026-12-27 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-27 14:45:00 → MDW 2026-12-27 16:15:00.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-25 12:35:00 → MDW 2026-12-25 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-25 12:35:00 → BNA 2026-12-25 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-25 14:45:00 → MDW 2026-12-25 16:15:00.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-25 18:55:00 → MDW 2026-12-25 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-25 18:55:00 → STL 2026-12-25 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-25 21:50:00 → MDW 2026-12-25 23:00:00.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-26 18:55:00 → MDW 2026-12-26 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-26 18:55:00 → STL 2026-12-26 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-26 21:50:00 → MDW 2026-12-26 23:00:00.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-03 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-27 18:55:00 → MDW 2026-12-27 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-27 18:55:00 → STL 2026-12-27 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-27 21:50:00 → MDW 2026-12-27 23:00:00.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-26 18:55:00 → MDW 2026-12-26 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-26 18:55:00 → STL 2026-12-26 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-26 21:50:00 → MDW 2026-12-26 23:00:00.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-26 12:35:00 → MDW 2026-12-26 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-26 12:35:00 → BNA 2026-12-26 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-26 14:45:00 → MDW 2026-12-26 16:15:00.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-02 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-25 12:35:00 → MDW 2026-12-25 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-25 12:35:00 → BNA 2026-12-25 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-25 14:45:00 → MDW 2026-12-25 16:15:00.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-26 12:35:00 → MDW 2026-12-26 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-26 12:35:00 → BNA 2026-12-26 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-26 14:45:00 → MDW 2026-12-26 16:15:00.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-03 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-26 18:55:00 → MDW 2026-12-26 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-26 18:55:00 → STL 2026-12-26 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-26 21:50:00 → MDW 2026-12-26 23:00:00.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-01 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-25 18:55:00 → MDW 2026-12-25 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-25 18:55:00 → STL 2026-12-25 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-25 21:50:00 → MDW 2026-12-25 23:00:00.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-01 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-25 12:35:00 → MDW 2026-12-25 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-25 12:35:00 → BNA 2026-12-25 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-25 14:45:00 → MDW 2026-12-25 16:15:00.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-02 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-27 18:55:00 → MDW 2026-12-27 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-27 18:55:00 → STL 2026-12-27 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-27 21:50:00 → MDW 2026-12-27 23:00:00.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-01 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-27 12:35:00 → MDW 2026-12-27 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-27 12:35:00 → BNA 2026-12-27 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-27 14:45:00 → MDW 2026-12-27 16:15:00.
  • Southwest Airlines WN1488: MDW 2027-01-01 12:25:00 → DCA 2027-01-01 15:15:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-02 · Axel-exclusive $358.60

  • Southwest Airlines WN1548 / WN4770: DCA 2026-12-25 18:55:00 → MDW 2026-12-25 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
    • WN1548: DCA 2026-12-25 18:55:00 → STL 2026-12-25 20:25:00; layover at STL: 85 minutes.
    • WN4770: STL 2026-12-25 21:50:00 → MDW 2026-12-25 23:00:00.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-26 → 2027-01-03 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-26 12:35:00 → MDW 2026-12-26 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-26 12:35:00 → BNA 2026-12-26 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-26 14:45:00 → MDW 2026-12-26 16:15:00.
  • Southwest Airlines WN4397: MDW 2027-01-03 10:10:00 → DCA 2027-01-03 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-27 → 2027-01-02 · Axel-exclusive $358.60

  • Southwest Airlines WN1515 / WN2062: DCA 2026-12-27 12:35:00 → MDW 2026-12-27 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
    • WN1515: DCA 2026-12-27 12:35:00 → BNA 2026-12-27 13:30:00; layover at BNA: 75 minutes.
    • WN2062: BNA 2026-12-27 14:45:00 → MDW 2026-12-27 16:15:00.
  • Southwest Airlines WN4397: MDW 2027-01-02 10:10:00 → DCA 2027-01-02 13:00:00; nonstop; 110 minutes. Local airport times.

2026-12-25 → 2027-01-01 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-25 09:45:00 → MDW 2026-12-25 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-25 09:45:00 → DTW 2026-12-25 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-25 12:44:00 → MDW 2026-12-25 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-01 13:31:00 → DCA 2027-01-01 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-01 13:31:00 → DTW 2027-01-01 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-01 17:07:00 → DCA 2027-01-01 18:39:00.

2026-12-27 → 2027-01-02 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-27 09:45:00 → MDW 2026-12-27 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-27 09:45:00 → DTW 2026-12-27 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-27 12:44:00 → MDW 2026-12-27 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-02 13:31:00 → DCA 2027-01-02 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-02 13:31:00 → DTW 2027-01-02 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-02 17:07:00 → DCA 2027-01-02 18:39:00.

2026-12-26 → 2027-01-03 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-26 09:45:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-26 09:45:00 → DTW 2026-12-26 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-03 13:31:00 → DCA 2027-01-03 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-03 13:31:00 → DTW 2027-01-03 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-03 17:07:00 → DCA 2027-01-03 18:39:00.

2026-12-27 → 2027-01-03 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-27 09:45:00 → MDW 2026-12-27 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-27 09:45:00 → DTW 2026-12-27 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-27 12:44:00 → MDW 2026-12-27 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-03 13:31:00 → DCA 2027-01-03 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-03 13:31:00 → DTW 2027-01-03 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-03 17:07:00 → DCA 2027-01-03 18:39:00.

2026-12-26 → 2027-01-01 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-26 09:45:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-26 09:45:00 → DTW 2026-12-26 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-01 13:31:00 → DCA 2027-01-01 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-01 13:31:00 → DTW 2027-01-01 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-01 17:07:00 → DCA 2027-01-01 18:39:00.

2026-12-25 → 2027-01-02 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-25 09:45:00 → MDW 2026-12-25 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-25 09:45:00 → DTW 2026-12-25 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-25 12:44:00 → MDW 2026-12-25 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-02 13:31:00 → DCA 2027-01-02 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-02 13:31:00 → DTW 2027-01-02 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-02 17:07:00 → DCA 2027-01-02 18:39:00.

2026-12-25 → 2027-01-03 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-25 09:45:00 → MDW 2026-12-25 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-25 09:45:00 → DTW 2026-12-25 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-25 12:44:00 → MDW 2026-12-25 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-03 13:31:00 → DCA 2027-01-03 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-03 13:31:00 → DTW 2027-01-03 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-03 17:07:00 → DCA 2027-01-03 18:39:00.

2026-12-26 → 2027-01-02 · Axel-exclusive $425.25

  • Delta Air Lines DL1558 / DL4688: DCA 2026-12-26 09:45:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
    • DL1558: DCA 2026-12-26 09:45:00 → DTW 2026-12-26 11:22:00; layover at DTW: 82 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Delta Air Lines DL4688 / DL2030: MDW 2027-01-02 13:31:00 → DCA 2027-01-02 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
    • DL4688: MDW 2027-01-02 13:31:00 → DTW 2027-01-02 15:44:00; layover at DTW: 83 minutes.
    • DL2030: DTW 2027-01-02 17:07:00 → DCA 2027-01-02 18:39:00.

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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  • This page: Washington (DCA) to Chicago (MDW) · Dec 25–Dec 27, 2026 · return Jan 1–Jan 3, 2027: 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 Washington, DC 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.