Travel with Axel, get the best price.

Route overview: Chicago to Portland (PDX) flight deals

Chicago (MDW) to Portland (PDX), Dec 18–20, 2026, return Dec 25–27, 2026: from $399 round trip

Chicago (MDW) to Portland (PDX), Dec 18–20, 2026, return Dec 25–27, 2026: from $399 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $399 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 18–25, 2026, 1 adult, economy, checked Oct 29, 2026.

MDW → PDX1 adulteconomyRound trip

72 flight options · 2 airlines

Nonstop flights

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
10:05 amMDW
4h 35m
Nonstop
12:40 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1PDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
10:10 amMDW
4h 35m
Nonstop
12:45 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
10:05 amMDW
4h 35m
Nonstop
12:40 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
10:05 amMDW
4h 35m
Nonstop
12:40 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1PDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
10:00 pmMDW
4h 40m
Nonstop
12:40 am+1PDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
10:00 pmMDW
4h 40m
Nonstop
12:40 am+1PDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
10:10 amMDW
4h 35m
Nonstop
12:45 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1PDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
10:10 amMDW
4h 35m
Nonstop
12:45 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
10:00 pmMDW
4h 40m
Nonstop
12:40 am+1PDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Fri, Dec 18 – Sat, Dec 26

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX
Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Dec 18–25, 2026 · 7 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $538 · 4★ The Society Hotel $585 · 5★ Sentinel Hotel $1,119

Hotels for these nights (Dec 18–26, 2026 · 8 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $618 · 4★ The Society Hotel $677 · 5★ Sentinel Hotel $1,289

Hotels for these nights (Dec 18–27, 2026 · 9 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $702 · 4★ The Society Hotel $769 · 5★ Sentinel Hotel $1,465

Hotels for these nights (Dec 19–25, 2026 · 6 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $458 · 4★ The Society Hotel $495 · 5★ Sentinel Hotel $949

Hotels for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $538 · 4★ The Society Hotel $587 · 5★ Sentinel Hotel $1,119

Hotels for these nights (Dec 19–27, 2026 · 8 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $622 · 4★ The Society Hotel $679 · 5★ Sentinel Hotel $1,295

Hotels for these nights (Dec 20–25, 2026 · 5 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $376 · 4★ The Society Hotel $405 · 5★ Sentinel Hotel $776

Hotels for these nights (Dec 20–26, 2026 · 6 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $456 · 4★ The Society Hotel $497 · 5★ Sentinel Hotel $946

Hotels for these nights (Dec 20–27, 2026 · 7 nights · 2 adults, 1 room): 3★ Red Lion Hotel Portland Airport $540 · 4★ The Society Hotel $589 · 5★ Sentinel Hotel $1,122

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MDW ⇄ PDX

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Explore this route

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

Chicago (MDW) to Portland (PDX), Dec 18–20, 2026, return Dec 25–27, 2026: from $399 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $399 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 18–25, 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)
2026-12-18 → 2026-12-27Southwest AirlinesWN1045 / WN335010:00:00→12:35:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $414.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Southwest AirlinesWN1045 / WN335010:00:00→12:35:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $414.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Southwest AirlinesWN3295 / WN335010:05:00→12:40:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Southwest AirlinesWN3295 / WN335021:30:00→00:15:00 4h 45m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Southwest AirlinesWN2087 / WN335010:10:00→12:45:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Southwest AirlinesWN3295 / WN335010:05:00→12:40:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Southwest AirlinesWN3295 / WN335010:05:00→12:40:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Southwest AirlinesWN3295 / WN335021:30:00→00:15:00 4h 45m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Southwest AirlinesWN3295 / WN335021:15:00→23:55:00 4h 40m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $414.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Southwest AirlinesWN1045 / WN335010:00:00→12:35:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $414.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-27Southwest AirlinesWN3295 / WN335021:15:00→23:55:00 4h 40m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $414.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Southwest AirlinesWN3295 / WN335021:15:00→23:55:00 4h 40m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $414.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Southwest AirlinesWN2578 / WN335022:00:00→00:40:00 4h 40m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Southwest AirlinesWN2578 / WN335022:00:00→00:40:00 4h 40m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Southwest AirlinesWN2087 / WN335010:10:00→12:45:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Southwest AirlinesWN3295 / WN335021:30:00→00:15:00 4h 45m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Southwest AirlinesWN2087 / WN335010:10:00→12:45:00 4h 35m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Southwest AirlinesWN2578 / WN335022:00:00→00:40:00 4h 40m nonstop · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $468.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-27Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-27Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-27Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-27Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-27Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-26Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $399.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-18 → 2026-12-25Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Southwest AirlinesWN4606 + WN1196 / WN335014:35:00→20:15:00 7h 40m 1 stop via DEN · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-18 → 2026-12-27Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Southwest AirlinesWN3174 + WN2916 / WN335010:00:00→15:35:00 7h 35m 1 stop via OAK · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Southwest AirlinesWN3035 + WN314 / WN335010:15:00→15:50:00 7h 35m 1 stop via SJC · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Southwest AirlinesWN3564 + WN2407 / WN335014:35:00→21:05:00 8h 30m 1 stop via LAS · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Southwest AirlinesWN2995 + WN969 / WN335005:05:00→10:50:00 7h 45m 1 stop via PHX · 23:30:00→05:15:00 3h 45m nonstopAxel-exclusive $448.502026-10-29T01:29:13Z
2026-12-20 → 2026-12-27Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $507.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-26Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $507.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-25Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $507.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-25Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $507.002026-10-29T01:29:13Z
2026-12-19 → 2026-12-27Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $507.002026-10-29T01:29:13Z
2026-12-20 → 2026-12-26Delta Air LinesDL4714 + DL2151 / DL411 + DL468417:29:00→23:46:00 8h 17m 1 stop via MSP · 23:20:00→09:46:00 8h 26m 1 stop via DTWAxel-exclusive $507.002026-10-29T01:29:13Z

Hotels in Portland, Oregon for these trips

Hotels: under a trip, hotels in Portland, Oregon 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 Portland, Oregon

Route overview: Chicago to Portland (PDX) flight deals

2026-12-18 → 2026-12-27 · Axel-exclusive $414.00

  • Southwest Airlines WN1045: MDW 2026-12-18 10:00:00 → PDX 2026-12-18 12:35:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $448.50

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-18 17:29:00 → PDX 2026-12-18 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-18 17:29:00 → MSP 2026-12-18 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-18 21:59:00 → PDX 2026-12-18 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-26 23:20:00 → MDW 2026-12-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-26 23:20:00 → DTW 2026-12-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-27 09:10:00 → MDW 2026-12-27 09:46:00.

2026-12-18 → 2026-12-25 · Axel-exclusive $414.00

  • Southwest Airlines WN1045: MDW 2026-12-18 10:00:00 → PDX 2026-12-18 12:35:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $468.00

  • Southwest Airlines WN3295: MDW 2026-12-19 10:05:00 → PDX 2026-12-19 12:40:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $468.00

  • Southwest Airlines WN3295: MDW 2026-12-20 21:30:00 → PDX 2026-12-21 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $468.00

  • Southwest Airlines WN2087: MDW 2026-12-20 10:10:00 → PDX 2026-12-20 12:45:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $468.00

  • Southwest Airlines WN3295: MDW 2026-12-19 10:05:00 → PDX 2026-12-19 12:40:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $468.00

  • Southwest Airlines WN3295: MDW 2026-12-19 10:05:00 → PDX 2026-12-19 12:40:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $468.00

  • Southwest Airlines WN3295: MDW 2026-12-20 21:30:00 → PDX 2026-12-21 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $414.00

  • Southwest Airlines WN3295: MDW 2026-12-18 21:15:00 → PDX 2026-12-18 23:55:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $414.00

  • Southwest Airlines WN1045: MDW 2026-12-18 10:00:00 → PDX 2026-12-18 12:35:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $414.00

  • Southwest Airlines WN3295: MDW 2026-12-18 21:15:00 → PDX 2026-12-18 23:55:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $414.00

  • Southwest Airlines WN3295: MDW 2026-12-18 21:15:00 → PDX 2026-12-18 23:55:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $468.00

  • Southwest Airlines WN2578: MDW 2026-12-19 22:00:00 → PDX 2026-12-20 00:40:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $468.00

  • Southwest Airlines WN2578: MDW 2026-12-19 22:00:00 → PDX 2026-12-20 00:40:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $468.00

  • Southwest Airlines WN2087: MDW 2026-12-20 10:10:00 → PDX 2026-12-20 12:45:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $468.00

  • Southwest Airlines WN3295: MDW 2026-12-20 21:30:00 → PDX 2026-12-21 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $468.00

  • Southwest Airlines WN2087: MDW 2026-12-20 10:10:00 → PDX 2026-12-20 12:45:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $468.00

  • Southwest Airlines WN2578: MDW 2026-12-19 22:00:00 → PDX 2026-12-20 00:40:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $399.00

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-18 14:35:00 → PDX 2026-12-18 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-18 14:35:00 → DEN 2026-12-18 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-18 18:25:00 → PDX 2026-12-18 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $399.00

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-18 14:35:00 → PDX 2026-12-18 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-18 14:35:00 → LAS 2026-12-18 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-18 18:40:00 → PDX 2026-12-18 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $399.00

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-18 05:05:00 → PDX 2026-12-18 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-18 05:05:00 → PHX 2026-12-18 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-18 09:00:00 → PDX 2026-12-18 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $399.00

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-18 14:35:00 → PDX 2026-12-18 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-18 14:35:00 → LAS 2026-12-18 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-18 18:40:00 → PDX 2026-12-18 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $399.00

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-18 10:00:00 → PDX 2026-12-18 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-18 10:00:00 → OAK 2026-12-18 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-18 13:55:00 → PDX 2026-12-18 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $399.00

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-18 10:00:00 → PDX 2026-12-18 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-18 10:00:00 → OAK 2026-12-18 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-18 13:55:00 → PDX 2026-12-18 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $399.00

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-18 05:05:00 → PDX 2026-12-18 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-18 05:05:00 → PHX 2026-12-18 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-18 09:00:00 → PDX 2026-12-18 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $399.00

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-18 14:35:00 → PDX 2026-12-18 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-18 14:35:00 → LAS 2026-12-18 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-18 18:40:00 → PDX 2026-12-18 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $399.00

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-18 10:15:00 → PDX 2026-12-18 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-18 10:15:00 → SJC 2026-12-18 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-18 14:00:00 → PDX 2026-12-18 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $399.00

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-18 10:15:00 → PDX 2026-12-18 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-18 10:15:00 → SJC 2026-12-18 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-18 14:00:00 → PDX 2026-12-18 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $399.00

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-18 14:35:00 → PDX 2026-12-18 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-18 14:35:00 → DEN 2026-12-18 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-18 18:25:00 → PDX 2026-12-18 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $399.00

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-18 14:35:00 → PDX 2026-12-18 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-18 14:35:00 → DEN 2026-12-18 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-18 18:25:00 → PDX 2026-12-18 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $399.00

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-18 10:15:00 → PDX 2026-12-18 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-18 10:15:00 → SJC 2026-12-18 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-18 14:00:00 → PDX 2026-12-18 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $399.00

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-18 10:00:00 → PDX 2026-12-18 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-18 10:00:00 → OAK 2026-12-18 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-18 13:55:00 → PDX 2026-12-18 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $399.00

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-18 05:05:00 → PDX 2026-12-18 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-18 05:05:00 → PHX 2026-12-18 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-18 09:00:00 → PDX 2026-12-18 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-19 05:05:00 → PDX 2026-12-19 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-19 05:05:00 → PHX 2026-12-19 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-19 09:00:00 → PDX 2026-12-19 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-20 10:15:00 → PDX 2026-12-20 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-20 10:15:00 → SJC 2026-12-20 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-20 14:00:00 → PDX 2026-12-20 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-19 14:35:00 → PDX 2026-12-19 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-19 14:35:00 → DEN 2026-12-19 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-19 18:25:00 → PDX 2026-12-19 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-20 10:15:00 → PDX 2026-12-20 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-20 10:15:00 → SJC 2026-12-20 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-20 14:00:00 → PDX 2026-12-20 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-20 14:35:00 → PDX 2026-12-20 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-20 14:35:00 → DEN 2026-12-20 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-20 18:25:00 → PDX 2026-12-20 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-19 10:15:00 → PDX 2026-12-19 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-19 10:15:00 → SJC 2026-12-19 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-19 14:00:00 → PDX 2026-12-19 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-20 10:00:00 → PDX 2026-12-20 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-20 10:00:00 → OAK 2026-12-20 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-20 13:55:00 → PDX 2026-12-20 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-19 10:15:00 → PDX 2026-12-19 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-19 10:15:00 → SJC 2026-12-19 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-19 14:00:00 → PDX 2026-12-19 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-20 14:35:00 → PDX 2026-12-20 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-20 14:35:00 → DEN 2026-12-20 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-20 18:25:00 → PDX 2026-12-20 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-20 14:35:00 → PDX 2026-12-20 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-20 14:35:00 → LAS 2026-12-20 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-20 18:40:00 → PDX 2026-12-20 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $448.50

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-18 17:29:00 → PDX 2026-12-18 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-18 17:29:00 → MSP 2026-12-18 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-18 21:59:00 → PDX 2026-12-18 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-25 23:20:00 → MDW 2026-12-26 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-25 23:20:00 → DTW 2026-12-26 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-26 09:10:00 → MDW 2026-12-26 09:46:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-20 10:15:00 → PDX 2026-12-20 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-20 10:15:00 → SJC 2026-12-20 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-20 14:00:00 → PDX 2026-12-20 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-20 05:05:00 → PDX 2026-12-20 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-20 05:05:00 → PHX 2026-12-20 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-20 09:00:00 → PDX 2026-12-20 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-20 14:35:00 → PDX 2026-12-20 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-20 14:35:00 → DEN 2026-12-20 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-20 18:25:00 → PDX 2026-12-20 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-19 14:35:00 → PDX 2026-12-19 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-19 14:35:00 → DEN 2026-12-19 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-19 18:25:00 → PDX 2026-12-19 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-20 05:05:00 → PDX 2026-12-20 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-20 05:05:00 → PHX 2026-12-20 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-20 09:00:00 → PDX 2026-12-20 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-19 10:00:00 → PDX 2026-12-19 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-19 10:00:00 → OAK 2026-12-19 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-19 13:55:00 → PDX 2026-12-19 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-19 10:00:00 → PDX 2026-12-19 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-19 10:00:00 → OAK 2026-12-19 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-19 13:55:00 → PDX 2026-12-19 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-19 05:05:00 → PDX 2026-12-19 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-19 05:05:00 → PHX 2026-12-19 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-19 09:00:00 → PDX 2026-12-19 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-19 14:35:00 → PDX 2026-12-19 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-19 14:35:00 → LAS 2026-12-19 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-19 18:40:00 → PDX 2026-12-19 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-19 14:35:00 → PDX 2026-12-19 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-19 14:35:00 → LAS 2026-12-19 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-19 18:40:00 → PDX 2026-12-19 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-19 14:35:00 → PDX 2026-12-19 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-19 14:35:00 → DEN 2026-12-19 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-19 18:25:00 → PDX 2026-12-19 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $448.50

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-18 17:29:00 → PDX 2026-12-18 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-18 17:29:00 → MSP 2026-12-18 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-18 21:59:00 → PDX 2026-12-18 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-27 23:20:00 → MDW 2026-12-28 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-27 23:20:00 → DTW 2026-12-28 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-28 09:10:00 → MDW 2026-12-28 09:46:00.

2026-12-19 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-19 14:35:00 → PDX 2026-12-19 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-19 14:35:00 → LAS 2026-12-19 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-19 18:40:00 → PDX 2026-12-19 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $448.50

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-20 10:00:00 → PDX 2026-12-20 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-20 10:00:00 → OAK 2026-12-20 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-20 13:55:00 → PDX 2026-12-20 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-27 23:30:00 → MDW 2026-12-28 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-19 10:00:00 → PDX 2026-12-19 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-19 10:00:00 → OAK 2026-12-19 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-19 13:55:00 → PDX 2026-12-19 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-20 05:05:00 → PDX 2026-12-20 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-20 05:05:00 → PHX 2026-12-20 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-20 09:00:00 → PDX 2026-12-20 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-20 10:00:00 → PDX 2026-12-20 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-20 10:00:00 → OAK 2026-12-20 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-20 13:55:00 → PDX 2026-12-20 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-20 14:35:00 → PDX 2026-12-20 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-20 14:35:00 → LAS 2026-12-20 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-20 18:40:00 → PDX 2026-12-20 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-19 10:15:00 → PDX 2026-12-19 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-19 10:15:00 → SJC 2026-12-19 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-19 14:00:00 → PDX 2026-12-19 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $448.50

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-20 14:35:00 → PDX 2026-12-20 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-20 14:35:00 → LAS 2026-12-20 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-20 18:40:00 → PDX 2026-12-20 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-25 23:30:00 → MDW 2026-12-26 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $448.50

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-19 05:05:00 → PDX 2026-12-19 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-19 05:05:00 → PHX 2026-12-19 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-19 09:00:00 → PDX 2026-12-19 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-26 23:30:00 → MDW 2026-12-27 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $507.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-20 17:29:00 → PDX 2026-12-20 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-20 17:29:00 → MSP 2026-12-20 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-20 21:59:00 → PDX 2026-12-20 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-27 23:20:00 → MDW 2026-12-28 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-27 23:20:00 → DTW 2026-12-28 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-28 09:10:00 → MDW 2026-12-28 09:46:00.

2026-12-19 → 2026-12-26 · Axel-exclusive $507.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-19 17:29:00 → PDX 2026-12-19 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-19 17:29:00 → MSP 2026-12-19 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-19 21:59:00 → PDX 2026-12-19 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-26 23:20:00 → MDW 2026-12-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-26 23:20:00 → DTW 2026-12-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-27 09:10:00 → MDW 2026-12-27 09:46:00.

2026-12-19 → 2026-12-25 · Axel-exclusive $507.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-19 17:29:00 → PDX 2026-12-19 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-19 17:29:00 → MSP 2026-12-19 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-19 21:59:00 → PDX 2026-12-19 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-25 23:20:00 → MDW 2026-12-26 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-25 23:20:00 → DTW 2026-12-26 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-26 09:10:00 → MDW 2026-12-26 09:46:00.

2026-12-20 → 2026-12-25 · Axel-exclusive $507.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-20 17:29:00 → PDX 2026-12-20 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-20 17:29:00 → MSP 2026-12-20 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-20 21:59:00 → PDX 2026-12-20 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-25 23:20:00 → MDW 2026-12-26 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-25 23:20:00 → DTW 2026-12-26 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-26 09:10:00 → MDW 2026-12-26 09:46:00.

2026-12-19 → 2026-12-27 · Axel-exclusive $507.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-19 17:29:00 → PDX 2026-12-19 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-19 17:29:00 → MSP 2026-12-19 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-19 21:59:00 → PDX 2026-12-19 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-27 23:20:00 → MDW 2026-12-28 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-27 23:20:00 → DTW 2026-12-28 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-28 09:10:00 → MDW 2026-12-28 09:46:00.

2026-12-20 → 2026-12-26 · Axel-exclusive $507.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-20 17:29:00 → PDX 2026-12-20 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-20 17:29:00 → MSP 2026-12-20 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-20 21:59:00 → PDX 2026-12-20 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-26 23:20:00 → MDW 2026-12-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-26 23:20:00 → DTW 2026-12-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-27 09:10:00 → MDW 2026-12-27 09:46:00.

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: Chicago (MDW) to Portland (PDX) · Dec 18–Dec 20, 2026 · return Dec 25–Dec 27, 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 Portland, Oregon 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 Chicago to Portland (PDX) 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.