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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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).
  • 10 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
Direct
PDX
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN1501
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08:30
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WN269
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17:00
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WN3245
20:05
20:10
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20:10
20:05
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20:05
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2025-01-15

Via Denver with Southwest Airlines

  • Total flight time: 5h 55m - 10h 45m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 22 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via DEN
 
PDX
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN2248
WN1080
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06:20
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WN4831
WN1453
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----
----
----
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07:40
WN1882
WN1453
07:55
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----
----
07:55
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WN1085
WN2055
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08:15
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08:15
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WN1090
WN2013
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----
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08:25
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WN2358
WN3403
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08:30
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WN1240
WN1453
10:15
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----
----
10:15
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10:15
WN1219
WN3155
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10:55
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----
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WN1266
WN2690
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11:35
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WN1450
WN3061
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----
----
----
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12:15
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WN3128
WN3841
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13:45
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13:45
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WN3128
WN2013
13:50
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----
----
13:50
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13:50
WN869
WN3841
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14:55
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14:55
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----
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WN4120
WN1880
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----
17:40
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----
----
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WN4120
WN1312
18:20
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----
----
18:20
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18:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2025-01-15

Via Sacramento with Southwest Airlines

  • Total flight time: 6h 40m - 10h 55m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 12 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via SMF
 
PDX
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN2248
WN1080
----
----
06:20
----
----
----
----
WN4831
WN1453
----
----
----
----
----
----
07:40
WN1882
WN1453
07:55
----
----
----
07:55
----
----
WN1085
WN2055
----
08:15
----
08:15
----
----
----
WN1090
WN2013
----
----
----
----
----
08:25
----
WN2358
WN3403
----
----
08:30
----
----
----
----
WN1240
WN1453
10:15
----
----
----
10:15
----
10:15
WN1219
WN3155
----
----
10:55
----
----
----
----
WN1266
WN2690
----
----
11:35
----
----
----
----
WN1450
WN3061
----
----
----
----
----
12:15
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WN3128
WN3841
----
13:45
----
13:45
----
----
----
WN3128
WN2013
13:50
----
----
----
13:50
----
13:50
WN869
WN3841
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14:55
----
14:55
----
----
----
WN4120
WN1880
----
----
17:40
----
----
----
----
WN4120
WN1312
18:20
----
----
----
18:20
----
18:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2025-01-15

Via Minneapolis with Delta Air Lines

  • Total flight time: 6h 06m - 8h 16m.
  • Sky Team Alliance
  • 6 flights per week
MDW
 
Via MSP
 
PDX
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
DL3792
DL1661
13:26
13:26
13:26
13:26
13:26
----
13:26
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2025-01-15

Via Detroit with Delta Air Lines

  • Total flight time: 6h 41m - 8h 43m.
  • Sky Team Alliance
  • 3 flights per week
MDW
 
Via DTW
 
PDX
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
DL3792
DL1661
13:26
13:26
13:26
13:26
13:26
----
13:26
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PDX

The timetable & schedule information was updated at 2025-01-15

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