Airlines with flights from Portland to Chicago

There are five airlines with scheduled flights between PWM and ORD. Both American Airlines and United operates non-stop flights from Portland International Jetport to Chicago O'Hare and the flight time is 3 hours and 6 minutes.

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Direct

$American Airlines from {( $airportFrom->city_name }} to Chicago$

Non-stop

3h 6min

Direct

$United Airlines from {( $airportFrom->city_name }} to Chicago$

Non-stop

2h 57min

Via Detroit

4h 25min

Via Dulles

4h 46min

Via Washington

4h 56min

Via New York

4h 57min

Via Philadelphia

5h 2min

Via New York

5h 11min

Via New York

5h 11min

Via Charlotte

5h 16min

Via New York

5h 22min

NEW

Via Cleveland

7h 21min

NEW

Via Pittsburgh

7h 38min

Via New York

5h 3min

Via Minneapolis

5h 43min

Via Minneapolis

6h 10min

NEW Starts 24/09

Via Greenville

9h 12min

Schedules

Non-stop with American Airlines

Total flight time: 3 hours and 6 minutes
One World Alliance
Chicago is a American Airlines hub.

21 flights per week
Embraer 175

Airbus A319
First class available

PWM

Direct

ORD

Flight

Mon

Aug 3

Tue

Aug 4

Wed

Aug 5

Thu

Aug 6

Fri

Aug 7

Sat

Aug 8

Sun

Aug 9

AA4391

06:00

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AA4499

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09:08

06:46

09:08

AA4741

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12:09

AA4488

12:16

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AA1291

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16:07

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AA4729

----

18:09

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18:09

AA4774

19:34

19:24

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

Non-stop with United Airlines

Total flight time: 2 hours and 57 minutes
Chicago is a United Airlines hub (Largest hub ).

14 flights per week
Boeing 737MAX 8 Passenger

Boeing 737-900 Passenger

Boeing 737-800 Passenger
Business and first class available

PWM

Direct

ORD

Flight

Mon

Aug 3

Tue

Aug 4

Wed

Aug 5

Thu

Aug 6

Fri

Aug 7

Sat

Aug 8

Sun

Aug 9

UA723

06:00

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06:00

UA1113

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06:00

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UA1182

17:00

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

Via Detroit with Delta Air Lines

Total flight time: 4h 25m - 6h 15m.
Sky Team Alliance

61 flights per week

PWM

Via DTW

ORD

Flight

Mon

Aug 3

Tue

Aug 4

Wed

Aug 5

Thu

Aug 6

Fri

Aug 7

Sat

Aug 8

Sun

Aug 9

DL426
DL2358

12:42

DL1821
DL1665

16:52

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

Via Dulles with United Airlines

Total flight time: 4h 46m - 6h 56m.
Chicago is a United Airlines hub (Largest hub ).

131 flights per week
Boeing 737MAX 8 Passenger

Boeing 737-900 Passenger

Boeing 737-800 Passenger

PWM

Via IAD

ORD

Flight

Mon

Aug 3

Tue

Aug 4

Wed

Aug 5

Thu

Aug 6

Fri

Aug 7

Sat

Aug 8

Sun

Aug 9

UA1926
UA1775

05:15

UA3465
UA2331

09:55

10:04

09:55

UA3459
UA2497

14:20

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14:20

UA3582
UA1738

19:16

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CHECK PRICES FOR PWM - ORD

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

Via Washington with American Airlines

Total flight time: 4h 56m - 7h 24m.
One World Alliance
Chicago is a American Airlines hub.

165 flights per week
Embraer 175

Airbus A319

PWM

Via DCA

ORD

Flight

Mon

Aug 3

Tue

Aug 4

Wed

Aug 5

Thu

Aug 6

Fri

Aug 7

Sat

Aug 8

Sun

Aug 9

AA4351
AA4360

05:41

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AA2712
AA2607

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06:00

AA5366
AA3254

11:47

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AA5528
AA1637

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12:18

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12:18

AA1453
AA1637

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12:24

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AA5664
AA2903

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17:11

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AA2884
AA2903

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17:13

AA2355
AA2903

17:16

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SHOW RETURN SCHEDULE

CLOSE RETURN SCHEDULE

CHECK PRICES FOR PWM - ORD

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

Via New York with American Airlines

Total flight time: 4h 57m - 7h 13m.
One World Alliance
Chicago is a American Airlines hub.

27 flights per week
Embraer 175

Airbus A319

PWM

Via LGA

ORD

Flight

Mon

Aug 3

Tue

Aug 4

Wed

Aug 5

Thu

Aug 6

Fri

Aug 7

Sat

Aug 8

Sun

Aug 9

AA4515
AA386

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10:00

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10:00

AA4486
AA2079