Airlines with flights from Portland to Chicago

There are two 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 50 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 3 hours and 50 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 19 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
PDX
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1148
06:00
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WN3130
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10:55
10:55
06:15
06:15
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WN4867
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07:35
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WN2992
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10:55
WN1351
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11:35
11:35
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WN3202
11:50
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WN3131
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23:30
23:30
23:30
23:30
23:30
23:30
WN3203
23:30
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Denver with Southwest Airlines

  • Total flight time: 5h 20m - 10h 00m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 171 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
PDX
 
Via DEN
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3195
WN755
05:50
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WN3123
WN4021
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06:15
WN3123
WN523
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06:45
06:45
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WN3123
WN1428
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06:45
06:45
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06:50
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WN4099
WN1539
07:10
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WN3124
WN2044
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07:40
WN4156
WN1110
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10:35
10:35
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WN4326
WN1561
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10:35
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WN654
WN4717
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10:55
10:55
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WN1658
WN1251
11:00
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WN4359
WN1562
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11:15
WN360
WN3439
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12:40
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WN1698
WN1563
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13:25
13:25
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WN3124
WN1563
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13:40
13:40
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WN2513
WN1563
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14:20
WN2519
WN1615
14:45
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Minneapolis with Delta Air Lines

  • Total flight time: 5h 32m - 6h 36m.
  • Sky Team Alliance
  • 28 flights per week
PDX
 
Via MSP
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL2359
DL4712
00:35
00:35
00:35
00:35
00:35
00:35
00:35
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Sacramento with Southwest Airlines

  • Total flight time: 6h 00m - 9h 55m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 30 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
PDX
 
Via SMF
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3140
WN346
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06:45
WN300
WN3769
10:00
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WN3142
WN3716
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19:55
19:55
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WN3213
WN3802
20:15
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WN2619
WN3716
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21:25
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 7h 27m - 8h 02m.
  • Sky Team Alliance
  • 32 flights per week
PDX
 
Via DTW
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL919
DL4684
23:15
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23:15
23:15
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23:15
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

The timetable & schedule information was updated at 2026-04-21

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Staying up-to-date with the airlines

At Airlineinformation.com you can learn all about the airlines operating around the world together with their destinations and where they operate. You will get a transparent overview of airlines with scheduled flights between any two destinations with non-stop or 1-stop flights regardless of price or availability.
Flight data on this page was last updated on 2026-07-21
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