Airlines with flights from Chicago to Portland

There are two airlines with scheduled flights between MDW and PDX. Southwest is the only airline with non-stop flights from Midway International Airport to Portland International and the flight time is 4 hours and 20 minutes.

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Choose airline

Schedules

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 20 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 22 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
Direct
PDX
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN2445
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08:15
WN2776
08:15
09:25
09:25
08:15
08:15
11:10
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WN495
14:05
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14:05
14:05
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WN2677
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17:05
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WN4346
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18:40
18:40
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----
----
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WN1004
21:35
22:10
22:10
21:35
21:35
20:35
22:25
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2024-03-15

Via Denver with Southwest Airlines

  • Total flight time: 5h 55m - 11h 05m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 40 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
 
Via DEN
 
PDX
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN4434
WN2433
05:10
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05:10
05:10
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WN5291
WN955
05:45
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05:45
05:45
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WN155
WN955
07:15
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07:15
07:15
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WN3786
WN955
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07:20
07:20
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----
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WN1100
WN855
07:55
08:15
08:15
07:55
07:55
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WN4259
WN855
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----
----
----
----
08:20
----
WN578
WN150
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08:20
08:20
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----
----
----
WN2435
WN855
08:30
----
----
08:30
08:30
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----
WN3477
WN3115
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----
----
----
----
----
09:30
WN3789
WN1577
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10:30
10:30
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WN3789
WN855
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10:30
10:30
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WN1467
WN2677
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----
----
----
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11:00
WN3959
WN1577
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11:40
11:40
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WN3992
WN1934
11:45
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11:45
11:45
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WN3789
WN3681
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----
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----
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12:45
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WN2473
WN1934
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----
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----
----
13:45
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WN4002
WN1934
13:50
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13:50
13:50
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WN4214
WN784
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13:55
13:55
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WN1866
WN5049
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14:45
14:45
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WN3128
WN1934
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----
----
----
----
15:50
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WN3758
WN4390
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16:05
16:05
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WN3288
WN1934
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----
----
----
----
16:15
WN1271
WN5049
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16:20
16:20
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WN1341
WN4390
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17:35
17:35
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----
WN4338
WN4390
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17:35
17:35
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WN2413
WN1552
17:50
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----
17:50
17:50
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WN5248
WN168
17:55
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----
17:55
17:55
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WN2557
WN4828
18:20
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----
18:20
18:20
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WN3062
WN168
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----
----
----
----
----
18:35
WN3571
WN4828
19:00
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19:00
19:00
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----
WN2089
WN4828
19:00
----
----
19:00
19:00
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----
WN2089
WN4390
----
19:00
19:00
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----
----
----
WN1341
WN168
----
----
----
----
----
19:05
----
WN2185
WN168
----
----
----
----
----
----
20:05
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2024-03-15

Via Minneapolis with Delta Air Lines

  • Total flight time: 5h 52m - 8h 24m.
  • Sky Team Alliance
  • 14 flights per week
MDW
 
Via MSP
 
PDX
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
DL3778
DL1661
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12:07
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DL3982
DL2151
14:24
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----
14:24
14:24
----
14:24
DL3799
DL1651
19:19
19:19
19:19
19:19
19:19
----
19:19
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2024-03-15

Via Sacramento with Southwest Airlines

  • Total flight time: 6h 30m - 10h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 4 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
 
Via SMF
 
PDX
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN4434
WN2433
05:10
----
----
05:10
05:10
----
----
WN5291
WN955
05:45
----
----
05:45
05:45
----
----
WN155
WN955
07:15
----
----
07:15
07:15
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----
WN3786
WN955
----
07:20
07:20
----
----
----
----
WN1100
WN855
07:55
08:15
08:15
07:55
07:55
----
----
WN4259
WN855
----
----
----
----
----
08:20
----
WN578
WN150
----
08:20
08:20
----
----
----
----
WN2435
WN855
08:30
----
----
08:30
08:30
----
----
WN3477
WN3115
----
----
----
----
----
----
09:30
WN3789
WN1577
----
10:30
10:30
----
----
----
----
WN3789
WN855
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10:30
10:30
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----
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WN1467
WN2677
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----
----
----
----
----
11:00
WN3959
WN1577
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11:40
11:40
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----
----
----
WN3992
WN1934
11:45
----
----
11:45
11:45
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----
WN3789
WN3681
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----
----
----
----
12:45
----
WN2473
WN1934
----
----
----
----
----
13:45
----
WN4002
WN1934
13:50
----
----
13:50
13:50
----
----
WN4214
WN784
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13:55
13:55
----
----
----
----
WN1866
WN5049
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14:45
14:45
----
----
----
----
WN3128
WN1934
----
----
----
----
----
15:50
----
WN3758
WN4390
----
16:05
16:05
----
----
----
----
WN3288
WN1934
----
----
----
----
----
----
16:15
WN1271
WN5049
----
16:20
16:20
----
----
----
----
WN1341
WN4390
----
17:35
17:35
----
----
----
----
WN4338
WN4390
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17:35
17:35
----
----
----
----
WN2413
WN1552
17:50
----
----
17:50
17:50
----
----
WN5248
WN168
17:55
----
----
17:55
17:55
----
----
WN2557
WN4828
18:20
----
----
18:20
18:20
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----
WN3062
WN168
----
----
----
----
----
----
18:35
WN3571
WN4828
19:00
----
----
19:00
19:00
----
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WN2089
WN4828
19:00
----
----
19:00
19:00
----
----
WN2089
WN4390
----
19:00
19:00
----
----
----
----
WN1341
WN168
----
----
----
----
----
19:05
----
WN2185
WN168
----
----
----
----
----
----
20:05
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2024-03-15

Via Saint Louis with Southwest Airlines

  • Total flight time: 6h 00m - 9h 40m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 3 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
 
Via STL
 
PDX
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN4434
WN2433
05:10
----
----
05:10
05:10
----
----
WN5291
WN955
05:45
----
----
05:45
05:45
----
----
WN155
WN955
07:15
----
----
07:15
07:15
----
----
WN3786
WN955
----
07:20
07:20
----
----
----
----
WN1100
WN855
07:55
08:15
08:15
07:55
07:55
----
----
WN4259
WN855
----
----
----
----
----
08:20
----
WN578
WN150
----
08:20
08:20
----
----
----
----
WN2435
WN855
08:30
----
----
08:30
08:30
----
----
WN3477
WN3115
----
----
----
----
----
----
09:30
WN3789
WN1577
----
10:30
10:30
----
----
----
----
WN3789
WN855
----
10:30
10:30
----
----
----
----
WN1467
WN2677
----
----
----
----
----
----
11:00
WN3959
WN1577
----
11:40
11:40
----
----
----
----
WN3992
WN1934
11:45
----
----
11:45
11:45
----
----
WN3789
WN3681
----
----
----
----
----
12:45
----
WN2473
WN1934
----
----
----
----
----
13:45
----
WN4002
WN1934
13:50
----
----
13:50
13:50
----
----
WN4214
WN784
----
13:55
13:55
----
----
----
----
WN1866
WN5049
----
14:45
14:45
----
----
----
----
WN3128
WN1934
----
----
----
----
----
15:50
----
WN3758
WN4390
----
16:05
16:05
----
----
----
----
WN3288
WN1934
----
----
----
----
----
----
16:15
WN1271
WN5049
----
16:20
16:20
----
----
----
----
WN1341
WN4390
----
17:35
17:35
----
----
----
----
WN4338
WN4390
----
17:35
17:35
----
----
----
----
WN2413
WN1552
17:50
----
----
17:50
17:50
----
----
WN5248
WN168
17:55
----
----
17:55
17:55
----
----
WN2557
WN4828
18:20
----
----
18:20
18:20
----
----
WN3062
WN168
----
----
----
----
----
----
18:35
WN3571
WN4828
19:00
----
----
19:00
19:00
----
----
WN2089
WN4828
19:00
----
----
19:00
19:00
----
----
WN2089
WN4390
----
19:00
19:00
----
----
----
----
WN1341
WN168
----
----
----
----
----
19:05
----
WN2185
WN168
----
----
----
----
----
----
20:05
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2024-03-15

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