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

Start your journey with just one click

Airline

1/27

Portland

toChicago

PDX-ORD

April 5, 2025

April 15, 2025

Sold byUnited Airlines

From

232USD Price subject to changes

Viewed:an hour ago

Roundtrip

Economy

2/27

Portland

toChicago

PDX-ORD

April 17, 2025

April 19, 2025

Sold byUnited Airlines

From

238USD Price subject to changes

Viewed:2 hours ago

Roundtrip

Economy

3/27

Portland

toChicago

PDX-ORD

April 11, 2025

April 15, 2025

Sold byUnited Airlines

From

242USD Price subject to changes

Viewed:an hour ago

Roundtrip

Economy

4/27

Portland

toChicago

PDX-ORD

April 5, 2025

April 14, 2025

Sold byUnited Airlines

From

243USD Price subject to changes

Viewed:an hour ago

Roundtrip

Economy

*Prices have been offered for round trips within the last 48 hours and might not be currently available. Not all Star Alliance Member Airlines or all fares/options are shown. Additional baggage fees, payment fees and fees for other optional services may apply. When booking, please check for restrictions on refunds, rebooking and baggage allowance that may apply. Prices may vary depending on the route and flights selected. Routings may include stopovers. Terms and conditions apply.

Weather in Chicago

Thursday

few clouds

13/03/2025

11°C

13/03/2025

few clouds

Friday

light rain

14/03/2025

18°C

14/03/2025

light rain

Saturday

heavy intensity rain

15/03/2025

18°C

15/03/2025

heavy intensity rain

Sunday

overcast clouds

16/03/2025

4°C

16/03/2025

overcast clouds

Monday

broken clouds

17/03/2025

13°C

17/03/2025

broken clouds

Tuesday

overcast clouds

18/03/2025

19°C

18/03/2025

overcast clouds

Wednesday

rain and snow

19/03/2025

9°C

19/03/2025

rain and snow

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 (19)

Sort by

Portland US
PDX07:00
4h 0m
No stops
Chicago US
ORD13:00
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 1693
  Portland. US
  PDX 07:00
  4h 0m
  1744 Miles
  Chicago. US
  ORD 13:00
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX11:00
3h 57m
No stops
Chicago US
ORD16:57
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 1335
  Portland. US
  PDX 11:00
  3h 57m
  1744 Miles
  Chicago. US
  ORD 16:57
  Boeing 737-800 Passenger
  Operated by United Airlines
Portland US
PDX23:58
3h 57m
No stops
Chicago US
ORD05:55
+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 2384
  Portland. US
  PDX 23:58
  3h 57m
  1744 Miles
  Chicago. US
  ORD 05:55
  Airbus A319 Passenger
  Operated by United Airlines
Portland US
PDX08:55
5h 56m
1 Stop
Chicago US
ORD16:51
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 1829
  Portland. US
  PDX 08:55
  2h 33m
  994 Miles
  Denver. US
  DEN 12:28
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 617
  Denver. US
  DEN 13:25
  2h 26m
  891 Miles
  Chicago. US
  ORD 16:51
  Airbus A321neo
  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 797
  Portland. US
  PDX 05:00
  2h 33m
  994 Miles
  Denver. US
  DEN 08:33
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 2329
  Denver. US
  DEN 09:40
  2h 34m
  891 Miles
  Chicago. US
  ORD 13:14
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX16:00
6h 23m
1 Stop
Chicago US
ORD00:23
+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 2190
  Portland. US
  PDX 16:00
  2h 34m
  994 Miles
  Denver. US
  DEN 19:34
  Boeing 737-800 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 377
  Denver. US
  DEN 20:55
  2h 28m
  891 Miles
  Chicago. US
  ORD 00:23
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX13:00
6h 28m
1 Stop
Chicago US
ORD21:28
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 616
  Portland. US
  PDX 13:00
  2h 34m
  994 Miles
  Denver. US
  DEN 16:34
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1898
  Denver. US
  DEN 17:55
  2h 33m
  891 Miles
  Chicago. US
  ORD 21:28
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX06:00
6h 55m
1 Stop
Chicago US
ORD14:55
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 1164
  Portland. US
  PDX 06:00
  1h 50m
  553 Miles
  San Francisco. US
  SFO 07:50
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 793
  San Francisco. US
  SFO 08:29
  4h 26m
  1851 Miles
  Chicago. US
  ORD 14:55
  Airbus A321neo
  Operated by United Airlines
Portland US
PDX07:45
7h 12m
1 Stop
Chicago US
ORD16:57
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 1702
  Portland. US
  PDX 07:45
  1h 54m
  553 Miles
  San Francisco. US
  SFO 09:39
  Boeing 737 MAX 9 Passenger / BBJ MAX 9
  Operated by United Airlines
2. Flight 2United Airlines UA 1612
  San Francisco. US
  SFO 10:35
  4h 22m
  1851 Miles
  Chicago. US
  ORD 16:57
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX19:31
7h 20m
1 Stop
Chicago US
ORD04:51
+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 436
  Portland. US
  PDX 19:31
  1h 55m
  553 Miles
  San Francisco. US
  SFO 21:26
  Airbus A320 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 2097
  San Francisco. US
  SFO 22:36
  4h 15m
  1851 Miles
  Chicago. US
  ORD 04:51
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX15:38
7h 22m
1 Stop
Chicago US
ORD01:00
+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 5486
  Portland. US
  PDX 15:38
  2h 0m
  553 Miles
  San Francisco. US
  SFO 17:38
  Embraer 175 (Enhanced Winglets)
  Operated by United Airlines
2. Flight 2United Airlines UA 2117
  San Francisco. US
  SFO 18:42
  4h 18m
  1851 Miles
  Chicago. US
  ORD 01:00
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX13:39
7h 52m
1 Stop
Chicago US
ORD23:31
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 1247
  Portland. US
  PDX 13:39
  1h 54m
  553 Miles
  San Francisco. US
  SFO 15:33
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 574
  San Francisco. US
  SFO 17:05
  4h 26m
  1851 Miles
  Chicago. US
  ORD 23:31
  Boeing 737 MAX 9 Passenger / BBJ MAX 9
  Operated by United Airlines
Portland US
PDX05:00
7h 54m
1 Stop
Chicago US
ORD14:54
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 797
  Portland. US
  PDX 05:00
  2h 33m
  994 Miles
  Denver. US
  DEN 08:33
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 1727
  Denver. US
  DEN 11:20
  2h 34m
  891 Miles
  Chicago. US
  ORD 14:54
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX13:00
7h 55m
1 Stop
Chicago US
ORD22:55
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 616
  Portland. US
  PDX 13:00
  2h 34m
  994 Miles
  Denver. US
  DEN 16:34
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 2258
  Denver. US
  DEN 19:27
  2h 28m
  891 Miles
  Chicago. US
  ORD 22:55
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX08:55
8h 0m
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 1829
  Portland. US
  PDX 08:55
  2h 33m
  994 Miles
  Denver. US
  DEN 12:28
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 1012
  Denver. US
  DEN 15:22
  2h 33m
  891 Miles
  Chicago. US
  ORD 18:55
  Boeing 737-900 Passenger
  Operated by United Airlines
Portland US
PDX10:05
8h 2m
1 Stop
Chicago US
ORD20:07
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 5463
  Portland. US
  PDX 10:05
  2h 3m
  553 Miles
  San Francisco. US
  SFO 12:08
  Embraer 175 (Enhanced Winglets)
  Operated by United Airlines
2. Flight 2United Airlines UA 2466
  San Francisco. US
  SFO 13:50
  4h 17m
  1851 Miles
  Chicago. US
  ORD 20:07
  Boeing 787-8
  Operated by United Airlines
Portland US
PDX19:31
8h 46m
1 Stop
Chicago US
ORD06:17
+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 436
  Portland. US
  PDX 19:31
  1h 55m
  553 Miles
  San Francisco. US
  SFO 21:26
  Airbus A320 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1112
  San Francisco. US
  SFO 23:59
  4h 18m
  1851 Miles
  Chicago. US
  ORD 06:17
  Boeing 777 Passenger
  Operated by United Airlines
Portland US
PDX06:00
8h 57m
1 Stop
Chicago US
ORD16:57
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 1164
  Portland. US
  PDX 06:00
  1h 50m
  553 Miles
  San Francisco. US
  SFO 07:50
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1612
  San Francisco. US
  SFO 10:35
  4h 22m
  1851 Miles
  Chicago. US
  ORD 16:57
  Boeing 757-300 Passenger
  Operated by United Airlines
Portland US
PDX10:05
9h 13m
1 Stop
Chicago US
ORD21:18
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 5463
  Portland. US
  PDX 10:05
  2h 3m
  553 Miles
  San Francisco. US
  SFO 12:08
  Embraer 175 (Enhanced Winglets)
  Operated by United Airlines
2. Flight 2United Airlines UA 1372
  San Francisco. US
  SFO 14:52
  4h 26m
  1851 Miles
  Chicago. US
  ORD 21:18
  Boeing 737-900 Passenger
  Operated by United Airlines

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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