Airlines with flights from Portland to Chicago

There are three airlines with scheduled flights between PDX and MDW. Southwest is the only airline with non-stop flights from Portland International to Midway International Airport and the flight time is 3 hours and 55 minutes.

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Schedules

Non-stop with Southwest Airlines

  • Total flight time: 3 hours and 55 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 9 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
PDX
Direct
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN4478
06:00
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----
----
----
----
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WN3049
----
11:30
11:30
11:30
11:30
06:35
06:25
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2024-11-19

Via Denver with Southwest Airlines

  • Total flight time: 5h 25m - 10h 00m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 21 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
PDX
 
Via DEN
 
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN133
WN290
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05:50
05:50
05:50
05:50
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----
WN2458
WN1406
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----
----
----
----
06:00
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WN2820
WN2912
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----
----
----
----
----
06:05
WN2476
WN757
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----
----
----
----
06:50
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WN1542
WN2337
07:30
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----
----
----
----
----
WN4221
WN2509
----
07:45
07:45
07:45
07:45
----
----
WN423
WN2912
14:05
----
----
----
----
----
08:25
WN423
WN5843
----
----
----
----
----
----
08:25
WN4221
WN5305
----
----
----
----
----
----
10:10
WN537
WN2436
10:10
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----
----
----
----
----
WN863
WN4514
11:15
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----
----
----
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WN863
WN343
11:15
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----
----
----
----
----
WN863
WN1389
11:15
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----
----
----
----
----
WN2078
WN419
----
13:10
13:10
13:10
13:10
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11:30
WN2078
WN4514
----
----
----
----
----
12:50
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WN2078
WN207
----
13:10
13:10
13:10
13:10
----
----
WN793
WN4514
----
----
----
----
----
----
15:35
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2024-11-19

Via Minneapolis with Delta Air Lines

  • Total flight time: 5h 51m - 7h 56m.
  • Sky Team Alliance
  • 14 flights per week
PDX
 
Via MSP
 
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
DL2359
DL3795
00:59
00:59
----
----
----
----
----
DL572
DL3858
23:15
23:15
23:15
23:15
23:13
23:13
23:13
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2024-11-19

Via Sacramento with Southwest Airlines

  • Total flight time: 6h 00m - 10h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 7 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
PDX
 
Via SMF
 
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN133
WN290
----
05:50
05:50
05:50
05:50
----
----
WN2458
WN1406
----
----
----
----
----
06:00
----
WN2820
WN2912
----
----
----
----
----
----
06:05
WN2476
WN757
----
----
----
----
----
06:50
----
WN1542
WN2337
07:30
----
----
----
----
----
----
WN4221
WN2509
----
07:45
07:45
07:45
07:45
----
----
WN423
WN2912
14:05
----
----
----
----
----
08:25
WN423
WN5843
----
----
----
----
----
----
08:25
WN4221
WN5305
----
----
----
----
----
----
10:10
WN537
WN2436
10:10
----
----
----
----
----
----
WN863
WN4514
11:15
----
----
----
----
----
----
WN863
WN343
11:15
----
----
----
----
----
----
WN863
WN1389
11:15
----
----
----
----
----
----
WN2078
WN419
----
13:10
13:10
13:10
13:10
----
11:30
WN2078
WN4514
----
----
----
----
----
12:50
----
WN2078
WN207
----
13:10
13:10
13:10
13:10
----
----
WN793
WN4514
----
----
----
----
----
----
15:35
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2024-11-19

Via Denver with Frontier Airlines

  • Total flight time: 5h 35m - 7h 47m.
  • Low-cost airline
  • Chicago is a Frontier Airlines focus city.
  • 3 flights per week
PDX
 
Via DEN
 
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
F91790
F92210
06:05
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2024-11-19

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