Flights from Portland (PDX) to Chicago (CHI)

Flight schedules from Portland to Chicago with Star Alliance member carriers

Please note that the flight schedules of our member carriers are subject to change on short notice. We recommend using our member airlines information page. for the latest flight updates, details on booking flexibility, as well as specific Frequent Flyer Program information.

Outbound (20)

Sort by

Portland US
PDX07:00
10h 47m
1 Stop
Chicago US
ORD19:47
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2406
  Portland. US
  PDX 07:00
  6h 48m
  1744 Miles
  Chicago. US
  ORD 19:47
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
Portland US
PDX07:08
3h 57m
No stops
Chicago US
ORD13:05
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 580
  Portland. US
  PDX 07:08
  3h 57m
  1744 Miles
  Chicago. US
  ORD 13:05
  Airbus A321neo
  Operated by United Airlines
Portland US
PDX10:56
3h 58m
No stops
Chicago US
ORD16:54
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1335
  Portland. US
  PDX 10:56
  3h 58m
  1744 Miles
  Chicago. US
  ORD 16:54
  Airbus A320 Passenger
  Operated by United Airlines
Portland US
PDX23:59
3h 49m
No stops
Chicago US
ORD05:48
+1 day/s
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1490
  Portland. US
  PDX 23:59
  3h 49m
  1744 Miles
  Chicago. US
  ORD 05:48
  Boeing 737-800 Passenger
  Operated by United Airlines
Portland US
PDX09:00
5h 56m
1 Stop
Chicago US
ORD16:56
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1974
  Portland. US
  PDX 09:00
  2h 31m
  994 Miles
  Denver. US
  DEN 12:31
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 617
  Denver. US
  DEN 13:25
  2h 31m
  891 Miles
  Chicago. US
  ORD 16:56
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX13:00
6h 11m
1 Stop
Chicago US
ORD21:11
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1942
  Portland. US
  PDX 13:00
  2h 31m
  994 Miles
  Denver. US
  DEN 16:31
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1898
  Denver. US
  DEN 17:40
  2h 31m
  891 Miles
  Chicago. US
  ORD 21:11
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX05:00
6h 14m
1 Stop
Chicago US
ORD13:14
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 459
  Portland. US
  PDX 05:00
  2h 31m
  994 Miles
  Denver. US
  DEN 08:31
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 2329
  Denver. US
  DEN 09:42
  2h 32m
  891 Miles
  Chicago. US
  ORD 13:14
  Airbus A321neo
  Operated by United Airlines
Portland US
PDX15:30
6h 27m
1 Stop
Chicago US
ORD23:57
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2190
  Portland. US
  PDX 15:30
  2h 31m
  994 Miles
  Denver. US
  DEN 19:01
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 377
  Denver. US
  DEN 20:25
  2h 32m
  891 Miles
  Chicago. US
  ORD 23:57
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX06:00
6h 41m
1 Stop
Chicago US
ORD14:41
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1164
  Portland. US
  PDX 06:00
  1h 50m
  553 Miles
  San Francisco. US
  SFO 07:50
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 534
  San Francisco. US
  SFO 08:30
  4h 11m
  1851 Miles
  Chicago. US
  ORD 14:41
  Boeing 777 Passenger
  Operated by United Airlines
Portland US
PDX08:00
6h 59m
1 Stop
Chicago US
ORD16:59
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2480
  Portland. US
  PDX 08:00
  1h 53m
  553 Miles
  San Francisco. US
  SFO 09:53
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1612
  San Francisco. US
  SFO 10:35
  4h 24m
  1851 Miles
  Chicago. US
  ORD 16:59
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX10:27
7h 3m
1 Stop
Chicago US
ORD19:30
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1823
  Portland. US
  PDX 10:27
  1h 53m
  553 Miles
  San Francisco. US
  SFO 12:20
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1791
  San Francisco. US
  SFO 13:15
  4h 15m
  1851 Miles
  Chicago. US
  ORD 19:30
  Boeing 787-8
  Operated by United Airlines
Portland US
PDX19:50
7h 10m
1 Stop
Chicago US
ORD05:00
+1 day/s
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1337
  Portland. US
  PDX 19:50
  1h 53m
  553 Miles
  San Francisco. US
  SFO 21:43
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1494
  San Francisco. US
  SFO 22:44
  4h 16m
  1851 Miles
  Chicago. US
  ORD 05:00
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX13:42
7h 27m
1 Stop
Chicago US
ORD23:09
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2633
  Portland. US
  PDX 13:42
  1h 51m
  553 Miles
  San Francisco. US
  SFO 15:33
  Boeing 737-800 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 2626
  San Francisco. US
  SFO 16:55
  4h 14m
  1851 Miles
  Chicago. US
  ORD 23:09
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX11:19
7h 46m
1 Stop
Chicago US
ORD21:05
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2106
  Portland. US
  PDX 11:19
  1h 51m
  553 Miles
  San Francisco. US
  SFO 13:10
  Boeing 737-800 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 468
  San Francisco. US
  SFO 14:45
  4h 20m
  1851 Miles
  Chicago. US
  ORD 21:05
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX05:00
7h 46m
1 Stop
Chicago US
ORD14:46
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 459
  Portland. US
  PDX 05:00
  2h 31m
  994 Miles
  Denver. US
  DEN 08:31
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 2312
  Denver. US
  DEN 11:15
  2h 31m
  891 Miles
  Chicago. US
  ORD 14:46
  Boeing 737 MAX 9 Passenger / BBJ MAX 9
  Operated by United Airlines
Portland US
PDX13:00
7h 51m
1 Stop
Chicago US
ORD22:51
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1942
  Portland. US
  PDX 13:00
  2h 31m
  994 Miles
  Denver. US
  DEN 16:31
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 2258
  Denver. US
  DEN 19:20
  2h 31m
  891 Miles
  Chicago. US
  ORD 22:51
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX09:00
7h 55m
1 Stop
Chicago US
ORD18:55
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1974
  Portland. US
  PDX 09:00
  2h 31m
  994 Miles
  Denver. US
  DEN 12:31
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1583
  Denver. US
  DEN 15:24
  2h 31m
  891 Miles
  Chicago. US
  ORD 18:55
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX19:50
8h 21m
1 Stop
Chicago US
ORD06:11
+1 day/s
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1337
  Portland. US
  PDX 19:50
  1h 53m
  553 Miles
  San Francisco. US
  SFO 21:43
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 476
  San Francisco. US
  SFO 23:59
  4h 12m
  1851 Miles
  Chicago. US
  ORD 06:11
  Boeing 777 Passenger
  Operated by United Airlines
Portland US
PDX10:27
8h 38m
1 Stop
Chicago US
ORD21:05
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1823
  Portland. US
  PDX 10:27
  1h 53m
  553 Miles
  San Francisco. US
  SFO 12:20
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 468
  San Francisco. US
  SFO 14:45
  4h 20m
  1851 Miles
  Chicago. US
  ORD 21:05
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX06:00
8h 59m
1 Stop
Chicago US
ORD16:59
Portland - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1164
  Portland. US
  PDX 06:00
  1h 50m
  553 Miles
  San Francisco. US
  SFO 07:50
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 1612
  San Francisco. US
  SFO 10:35
  4h 24m
  1851 Miles
  Chicago. US
  ORD 16:59
  Boeing 737-900 Passenger
  Operated by United Airlines

Flights from Portland (PDX) to Chicago (CHI) with Star Alliance

Weather in Chicago

Flight schedules from Portland to Chicago with Star Alliance member carriers

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago

Portland - Chicago