Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline American Airlines

The cheapest airline(s) flying from Portland to Chicago is American Airlines.

  • American Airlines American Airlines
  • United Airlines United Airlines
  • Southwest Airlines Southwest Airlines
Cheapest Month February

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Portland to Chicago is February.

  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
Cheapest Day of the Week Saturday

The cheapest day(s) of the week to fly from Portland to Chicago is Saturday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

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      • Availability
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      • 07:30 PWM
        09:44 ORD
        3Hrs, 14m Direct
      • PWMPortland Airport 07:30 - ORD 09:44 3h 14m Direct
      • PWMPortland Airport 07:30
      • ORDChicago O'Hare International Airport 09:44
      • 3h 14m
      • Direct
      • United Airlines (UA 3605)Embraer 175
      • United Airlines (UA 3605)
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        • S
      • Embraer 175
      • 16:15 PWM
        18:27 ORD
        3Hrs, 12m Direct
      • PWMPortland Airport 16:15 - ORD 18:27 3h 12m Direct
      • PWMPortland Airport 16:15
      • ORDChicago O'Hare International Airport 18:27
      • 3h 12m
      • Direct
      • United Airlines (UA 5517)Embraer 175
      • United Airlines (UA 5517)
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        • S
      • Embraer 175
      • 19:16 PWM
        23:25 ORD
        5Hrs, 09m 1 Stop (IAD)
      • PWMPortland Airport 19:16 - ORD 23:25 5h 09m 1 Stop (IAD) Washington
      • PWMPortland Airport 19:16
        IADWashington Dulles International Airport 22:20
      • IADWashington Dulles International Airport 21:20
        ORDChicago O'Hare International Airport 23:25
      • 5h 09m (1h)
      • 1 Stop IAD · Washington 1h
      • United Airlines (UA 3582)Embraer 175
        United Airlines (UA 1738)Boeing 757 200 Series
      • United Airlines (UA 3582)
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        • S
      • 05:20 PWM
        09:55 ORD
        5Hrs, 35m 1 Stop (IAD)
      • PWMPortland Airport 05:20 - ORD 09:55 5h 35m 1 Stop (IAD) Washington
      • PWMPortland Airport 05:20
        IADWashington Dulles International Airport 08:35
      • IADWashington Dulles International Airport 07:14
        ORDChicago O'Hare International Airport 09:55
      • 5h 35m (1h 21m)
      • 1 Stop IAD · Washington 1h 21m
      • United Airlines (UA 1668)Boeing 737 800
        United Airlines (UA 1710)Airbus
      • United Airlines (UA 1668)
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        • S
      • 05:25 PWM
        10:55 ORD
        6Hrs, 30m 1 Stop (DCA)
      • PWMPortland Airport 05:25 - ORD 10:55 6h 30m 1 Stop (DCA) Washington
      • PWMPortland Airport 05:25
        DCAWashington Ronald Reagan National Airport 09:29
      • DCAWashington Ronald Reagan National Airport 07:28
        ORDChicago O'Hare International Airport 10:55
      • 6h 30m (2h 01m)
      • 1 Stop DCA · Washington 2h 01m
      • American Airlines (AA 5309)Crj 700 Canadair Regional
        American Airlines (AA 4391)Embraer Emb 175
      • American Airlines (AA 5309)
        • -
        • -
        • -
        • -
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        • S
        • -
      • 05:25 PWM
        11:02 ORD
        6Hrs, 37m 1 Stop (DCA)
      • PWMPortland Airport 05:25 - ORD 11:02 6h 37m 1 Stop (DCA) Washington
      • PWMPortland Airport 05:25
        DCAWashington Ronald Reagan National Airport 09:44
      • DCAWashington Ronald Reagan National Airport 07:28
        ORDChicago O'Hare International Airport 11:02
      • 6h 37m (2h 16m)
      • 1 Stop DCA · Washington 2h 16m
      • American Airlines (AA 5309)Crj 700 Canadair Regional
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 5309)
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      • 05:25 PWM
        11:04 ORD
        6Hrs, 39m 1 Stop (DCA)
      • PWMPortland Airport 05:25 - ORD 11:04 6h 39m 1 Stop (DCA) Washington
      • PWMPortland Airport 05:25
        DCAWashington Ronald Reagan National Airport 09:37
      • DCAWashington Ronald Reagan National Airport 07:28
        ORDChicago O'Hare International Airport 11:04
      • 6h 39m (2h 09m)
      • 1 Stop DCA · Washington 2h 09m
      • American Airlines (AA 5309)Crj 700 Canadair Regional
        American Airlines (AA 4391)Embraer Emb 175
      • American Airlines (AA 5309)
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      • 05:25 PWM
        11:07 ORD
        6Hrs, 42m 1 Stop (DCA)
      • PWMPortland Airport 05:25 - ORD 11:07 6h 42m 1 Stop (DCA) Washington
      • PWMPortland Airport 05:25
        DCAWashington Ronald Reagan National Airport 09:40
      • DCAWashington Ronald Reagan National Airport 07:28
        ORDChicago O'Hare International Airport 11:07
      • 6h 42m (2h 12m)
      • 1 Stop DCA · Washington 2h 12m
      • American Airlines (AA 5309)Crj 700 Canadair Regional
        American Airlines (AA 4766)Embraer Emb 175
      • American Airlines (AA 5309)
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      • 05:30 PWM
        10:20 MDW
        5Hrs, 50m 1 Stop (BWI)
      • PWMPortland Airport 05:30 - MDW 10:20 5h 50m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 05:30
        BWIBaltimore Washington International Airport 09:10
      • BWIBaltimore Washington International Airport 07:15
        MDWChicago Midway Airport 10:20
      • 5h 50m (1h 55m)
      • 1 Stop BWI · Baltimore 1h 55m
      • Southwest Airlines (WN 2258)Boeing 737 800
        Southwest Airlines (WN 6315)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2258)
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      • 05:39 PWM
        11:01 ORD
        6Hrs, 22m 1 Stop (CLT)
      • PWMPortland Airport 05:39 - ORD 11:01 6h 22m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 05:39
        CLTCharlotte Airport 09:40
      • CLTCharlotte Airport 08:25
        ORDChicago O'Hare International Airport 11:01
      • 6h 22m (1h 15m)
      • 1 Stop CLT · Charlotte 1h 15m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 2981)
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      • 05:39 PWM
        12:07 ORD
        7Hrs, 28m 1 Stop (CLT)
      • PWMPortland Airport 05:39 - ORD 12:07 7h 28m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 05:39
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 08:25
        ORDChicago O'Hare International Airport 12:07
      • 7h 28m (2h 34m)
      • 1 Stop CLT · Charlotte 2h 34m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 2981)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:39 PWM
        12:12 ORD
        7Hrs, 33m 1 Stop (CLT)
      • PWMPortland Airport 05:39 - ORD 12:12 7h 33m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 05:39
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 08:25
        ORDChicago O'Hare International Airport 12:12
      • 7h 33m (2h 36m)
      • 1 Stop CLT · Charlotte 2h 36m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 2981)
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      • 05:39 PWM
        12:12 ORD
        7Hrs, 33m 1 Stop (CLT)
      • PWMPortland Airport 05:39 - ORD 12:12 7h 33m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 05:39
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 08:25
        ORDChicago O'Hare International Airport 12:12
      • 7h 33m (2h 36m)
      • 1 Stop CLT · Charlotte 2h 36m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 2279)Airbus A321 Neo
      • American Airlines (AA 2981)
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      • 06:00 PWM
        10:41 ORD
        5Hrs, 41m 1 Stop (PHL)
      • PWMPortland Airport 06:00 - ORD 10:41 5h 41m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 06:00
        PHLPhiladelphia International Airport 09:14
      • PHLPhiladelphia International Airport 07:40
        ORDChicago O'Hare International Airport 10:41
      • 5h 41m (1h 34m)
      • 1 Stop PHL · Philadelphia 1h 34m
      • American Airlines (AA 5362)Crj 700 Canadair Regional
        American Airlines (AA 1606)Airbus
      • American Airlines (AA 5362)
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        • -
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        • S
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      • 06:00 PWM
        10:53 ORD
        5Hrs, 53m 1 Stop (PHL)
      • PWMPortland Airport 06:00 - ORD 10:53 5h 53m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 06:00
        PHLPhiladelphia International Airport 09:24
      • PHLPhiladelphia International Airport 07:40
        ORDChicago O'Hare International Airport 10:53
      • 5h 53m (1h 44m)
      • 1 Stop PHL · Philadelphia 1h 44m
      • American Airlines (AA 5362)Crj 700 Canadair Regional
        American Airlines (AA 1606)Airbus
      • American Airlines (AA 5362)
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      • 06:00 PWM
        11:38 ORD
        6Hrs, 38m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 11:38 6h 38m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 07:45
        ORDChicago O'Hare International Airport 11:38
      • 6h 38m (2h 15m)
      • 1 Stop EWR · New York City 2h 15m
      • United Airlines (UA 2455)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2455)
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      • 06:00 PWM
        11:38 ORD
        6Hrs, 38m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 11:38 6h 38m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 07:45
        ORDChicago O'Hare International Airport 11:38
      • 6h 38m (2h 15m)
      • 1 Stop EWR · New York City 2h 15m
      • United Airlines (UA 2455)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 2455)
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        • S
      • 06:00 PWM
        12:15 ORD
        7Hrs, 15m 1 Stop (PHL)
      • PWMPortland Airport 06:00 - ORD 12:15 7h 15m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 06:00
        PHLPhiladelphia International Airport 10:41
      • PHLPhiladelphia International Airport 07:40
        ORDChicago O'Hare International Airport 12:15
      • 7h 15m (3h 01m)
      • 1 Stop PHL · Philadelphia 3h 01m
      • American Airlines (AA 5362)Crj 700 Canadair Regional
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 5362)
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      • 06:29 PWM
        12:12 ORD
        6Hrs, 43m 1 Stop (CLT)
      • PWMPortland Airport 06:29 - ORD 12:12 6h 43m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 06:29
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 09:15
        ORDChicago O'Hare International Airport 12:12
      • 6h 43m (1h 46m)
      • 1 Stop CLT · Charlotte 1h 46m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 2981)
        • -
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      • 11:10 PWM
        16:40 MDW
        6Hrs, 30m 1 Stop (BWI)
      • PWMPortland Airport 11:10 - MDW 16:40 6h 30m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 11:10
        BWIBaltimore Washington International Airport 15:35
      • BWIBaltimore Washington International Airport 12:50
        MDWChicago Midway Airport 16:40
      • 6h 30m (2h 45m)
      • 1 Stop BWI · Baltimore 2h 45m
      • Southwest Airlines (WN 2258)Boeing 737 700
        Southwest Airlines (WN 4710)Boeing 737 800
      • Southwest Airlines (WN 2258)
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      • 11:12 PWM
        17:04 ORD
        6Hrs, 52m 1 Stop (EWR)
      • PWMPortland Airport 11:12 - ORD 17:04 6h 52m 1 Stop (EWR) New York City
      • PWMPortland Airport 11:12
        EWRNewark Liberty International Airport 15:25
      • EWRNewark Liberty International Airport 13:02
        ORDChicago O'Hare International Airport 17:04
      • 6h 52m (2h 23m)
      • 1 Stop EWR · New York City 2h 23m
      • United Airlines (UA 3623)Embraer 175
        United Airlines (UA 605)Boeing 737 900
      • United Airlines (UA 3623)
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      • 11:12 PWM
        17:59 ORD
        7Hrs, 47m 1 Stop (EWR)
      • PWMPortland Airport 11:12 - ORD 17:59 7h 47m 1 Stop (EWR) New York City
      • PWMPortland Airport 11:12
        EWRNewark Liberty International Airport 16:20
      • EWRNewark Liberty International Airport 13:02
        ORDChicago O'Hare International Airport 17:59
      • 7h 47m (3h 18m)
      • 1 Stop EWR · New York City 3h 18m
      • United Airlines (UA 3623)Embraer 175
        United Airlines (UA 1789)Boeing 737 900
      • United Airlines (UA 3623)
        • M
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        • -
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      • 11:15 PWM
        14:50 MDW
        4Hrs, 35m 1 Stop (BWI)
      • PWMPortland Airport 11:15 - MDW 14:50 4h 35m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 11:15
        BWIBaltimore Washington International Airport 13:45
      • BWIBaltimore Washington International Airport 12:55
        MDWChicago Midway Airport 14:50
      • 4h 35m (50m)
      • 1 Stop BWI · Baltimore 50m
      • Southwest Airlines (WN 429)Boeing 737 700
        Southwest Airlines (WN 1689)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 429)
        • M
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      • 12:15 PWM
        18:09 ORD
        6Hrs, 54m 1 Stop (CLT)
      • PWMPortland Airport 12:15 - ORD 18:09 6h 54m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 12:15
        CLTCharlotte Airport 16:58
      • CLTCharlotte Airport 14:59
        ORDChicago O'Hare International Airport 18:09
      • 6h 54m (1h 59m)
      • 1 Stop CLT · Charlotte 1h 59m
      • American Airlines (AA 885)Airbus
        American Airlines (AA 2569)Boeing 737 800
      • American Airlines (AA 885)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:23 PWM
        18:21 ORD
        6Hrs, 58m 1 Stop (DCA)
      • PWMPortland Airport 12:23 - ORD 18:21 6h 58m 1 Stop (DCA) Washington
      • PWMPortland Airport 12:23
        DCAWashington Ronald Reagan National Airport 16:59
      • DCAWashington Ronald Reagan National Airport 14:26
        ORDChicago O'Hare International Airport 18:21
      • 6h 58m (2h 33m)
      • 1 Stop DCA · Washington 2h 33m
      • American Airlines (AA 5056)Crj 700 Canadair Regional
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 5056)
        • -
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        • -
        • -
        • -
        • S
        • -
      • 12:23 PWM
        18:36 ORD
        7Hrs, 13m 1 Stop (DCA)
      • PWMPortland Airport 12:23 - ORD 18:36 7h 13m 1 Stop (DCA) Washington
      • PWMPortland Airport 12:23
        DCAWashington Ronald Reagan National Airport 17:13
      • DCAWashington Ronald Reagan National Airport 14:26
        ORDChicago O'Hare International Airport 18:36
      • 7h 13m (2h 47m)
      • 1 Stop DCA · Washington 2h 47m
      • American Airlines (AA 5056)Crj 700 Canadair Regional
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 5056)
        • M
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      • 12:56 PWM
        16:54 ORD
        4Hrs, 58m 1 Stop (PHL)
      • PWMPortland Airport 12:56 - ORD 16:54 4h 58m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 12:56
        PHLPhiladelphia International Airport 15:26
      • PHLPhiladelphia International Airport 14:37
        ORDChicago O'Hare International Airport 16:54
      • 4h 58m (49m)
      • 1 Stop PHL · Philadelphia 49m
      • American Airlines (AA 5372)Crj 700 Canadair Regional
        American Airlines (AA 1309)Airbus
      • American Airlines (AA 5372)
        • M
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        • S
        • S
      • 12:56 PWM
        17:17 ORD
        5Hrs, 21m 1 Stop (PHL)
      • PWMPortland Airport 12:56 - ORD 17:17 5h 21m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 12:56
        PHLPhiladelphia International Airport 15:47
      • PHLPhiladelphia International Airport 14:37
        ORDChicago O'Hare International Airport 17:17
      • 5h 21m (1h 10m)
      • 1 Stop PHL · Philadelphia 1h 10m
      • American Airlines (AA 5372)Crj 700 Canadair Regional
        American Airlines (AA 2264)Airbus
      • American Airlines (AA 5372)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 13:15 PWM
        18:45 MDW
        6Hrs, 30m 1 Stop (BWI)
      • PWMPortland Airport 13:15 - MDW 18:45 6h 30m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 13:15
        BWIBaltimore Washington International Airport 17:40
      • BWIBaltimore Washington International Airport 14:50
        MDWChicago Midway Airport 18:45
      • 6h 30m (2h 50m)
      • 1 Stop BWI · Baltimore 2h 50m
      • Southwest Airlines (WN 2258)Boeing 737 700
        Southwest Airlines (WN 1291)Boeing 737 800
      • Southwest Airlines (WN 2258)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 13:38 PWM
        18:55 ORD
        6Hrs, 17m 1 Stop (IAD)
      • PWMPortland Airport 13:38 - ORD 18:55 6h 17m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:38
        IADWashington Dulles International Airport 17:35
      • IADWashington Dulles International Airport 15:45
        ORDChicago O'Hare International Airport 18:55
      • 6h 17m (1h 50m)
      • 1 Stop IAD · Washington 1h 50m
      • United Airlines (UA 4322)Embraer
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 4322)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 13:38 PWM
        18:55 ORD
        6Hrs, 17m 1 Stop (IAD)
      • PWMPortland Airport 13:38 - ORD 18:55 6h 17m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:38
        IADWashington Dulles International Airport 17:35
      • IADWashington Dulles International Airport 15:45
        ORDChicago O'Hare International Airport 18:55
      • 6h 17m (1h 50m)
      • 1 Stop IAD · Washington 1h 50m
      • United Airlines (UA 4322)Embraer
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 4322)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:55 PWM
        18:42 ORD
        5Hrs, 47m 1 Stop (IAD)
      • PWMPortland Airport 13:55 - ORD 18:42 5h 47m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:55
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 15:53
        ORDChicago O'Hare International Airport 18:42
      • 5h 47m (1h 29m)
      • 1 Stop IAD · Washington 1h 29m
      • United Airlines (UA 6052)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 6052)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 13:55 PWM
        18:42 ORD
        5Hrs, 47m 1 Stop (IAD)
      • PWMPortland Airport 13:55 - ORD 18:42 5h 47m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:55
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 15:53
        ORDChicago O'Hare International Airport 18:42
      • 5h 47m (1h 29m)
      • 1 Stop IAD · Washington 1h 29m
      • United Airlines (UA 6052)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 6052)
        • -
        • T
        • -
        • -
        • F
        • -
        • -
      • 13:55 PWM
        18:42 ORD
        5Hrs, 47m 1 Stop (IAD)
      • PWMPortland Airport 13:55 - ORD 18:42 5h 47m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:55
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 15:53
        ORDChicago O'Hare International Airport 18:42
      • 5h 47m (1h 29m)
      • 1 Stop IAD · Washington 1h 29m
      • United Airlines (UA 6052)Embraer 175
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 6052)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 14:15 PWM
        20:00 MDW
        6Hrs, 45m 1 Stop (BWI)
      • PWMPortland Airport 14:15 - MDW 20:00 6h 45m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 14:15
        BWIBaltimore Washington International Airport 18:55
      • BWIBaltimore Washington International Airport 15:50
        MDWChicago Midway Airport 20:00
      • 6h 45m (3h 05m)
      • 1 Stop BWI · Baltimore 3h 05m
      • Southwest Airlines (WN 3857)Boeing 737 800
        Southwest Airlines (WN 1014)Boeing 737 700
      • Southwest Airlines (WN 3857)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 14:17 PWM
        18:36 ORD
        5Hrs, 19m 1 Stop (DCA)
      • PWMPortland Airport 14:17 - ORD 18:36 5h 19m 1 Stop (DCA) Washington
      • PWMPortland Airport 14:17
        DCAWashington Ronald Reagan National Airport 17:13
      • DCAWashington Ronald Reagan National Airport 16:19
        ORDChicago O'Hare International Airport 18:36
      • 5h 19m (54m)
      • 1 Stop DCA · Washington 54m
      • American Airlines (AA 5469)Crj 700 Canadair Regional
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 5469)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 15:20 PWM
        20:35 MDW
        6Hrs, 15m 1 Stop (BWI)
      • PWMPortland Airport 15:20 - MDW 20:35 6h 15m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 15:20
        BWIBaltimore Washington International Airport 19:30
      • BWIBaltimore Washington International Airport 17:00
        MDWChicago Midway Airport 20:35
      • 6h 15m (2h 30m)
      • 1 Stop BWI · Baltimore 2h 30m
      • Southwest Airlines (WN 3053)Boeing 737 800
        Southwest Airlines (WN 854)Boeing 737 700
      • Southwest Airlines (WN 3053)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 15:55 PWM
        21:15 MDW
        6Hrs, 20m 1 Stop (BWI)
      • PWMPortland Airport 15:55 - MDW 21:15 6h 20m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 15:55
        BWIBaltimore Washington International Airport 20:10
      • BWIBaltimore Washington International Airport 17:35
        MDWChicago Midway Airport 21:15
      • 6h 20m (2h 35m)
      • 1 Stop BWI · Baltimore 2h 35m
      • Southwest Airlines (WN 3053)Boeing 737 700
        Southwest Airlines (WN 4710)Boeing 737 800
      • Southwest Airlines (WN 3053)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 15:55 PWM
        21:30 ORD
        6Hrs, 35m 1 Stop (BWI)
      • PWMPortland Airport 15:55 - ORD 21:30 6h 35m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 15:55
        BWIBaltimore Washington International Airport 20:10
      • BWIBaltimore Washington International Airport 17:35
        ORDChicago O'Hare International Airport 21:30
      • 6h 35m (2h 35m)
      • 1 Stop BWI · Baltimore 2h 35m
      • Southwest Airlines (WN 3053)Boeing 737 700
        Southwest Airlines (WN 1849)Boeing 737 700
      • Southwest Airlines (WN 3053)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 16:05 PWM
        21:52 ORD
        6Hrs, 47m 1 Stop (EWR)
      • PWMPortland Airport 16:05 - ORD 21:52 6h 47m 1 Stop (EWR) New York City
      • PWMPortland Airport 16:05
        EWRNewark Liberty International Airport 20:10
      • EWRNewark Liberty International Airport 17:58
        ORDChicago O'Hare International Airport 21:52
      • 6h 47m (2h 12m)
      • 1 Stop EWR · New York City 2h 12m
      • United Airlines (UA 3620)Embraer 175
        United Airlines (UA 546)Boeing 737 900
      • United Airlines (UA 3620)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 16:05 PWM
        21:57 ORD
        6Hrs, 52m 1 Stop (EWR)
      • PWMPortland Airport 16:05 - ORD 21:57 6h 52m 1 Stop (EWR) New York City
      • PWMPortland Airport 16:05
        EWRNewark Liberty International Airport 20:15
      • EWRNewark Liberty International Airport 17:58
        ORDChicago O'Hare International Airport 21:57
      • 6h 52m (2h 17m)
      • 1 Stop EWR · New York City 2h 17m
      • United Airlines (UA 3620)Embraer 175
        United Airlines (UA 546)Boeing 737 900
      • United Airlines (UA 3620)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 16:15 PWM
        20:07 ORD
        4Hrs, 52m 1 Stop (PHL)
      • PWMPortland Airport 16:15 - ORD 20:07 4h 52m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 16:15
        PHLPhiladelphia International Airport 18:35
      • PHLPhiladelphia International Airport 17:54
        ORDChicago O'Hare International Airport 20:07
      • 4h 52m (41m)
      • 1 Stop PHL · Philadelphia 41m
      • American Airlines (AA 5312)Canadair Regional
        American Airlines (AA 490)Airbus
      • American Airlines (AA 5312)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 16:15 PWM
        22:58 ORD
        7Hrs, 43m 1 Stop (PHL)
      • PWMPortland Airport 16:15 - ORD 22:58 7h 43m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 16:15
        PHLPhiladelphia International Airport 21:20
      • PHLPhiladelphia International Airport 17:54
        ORDChicago O'Hare International Airport 22:58
      • 7h 43m (3h 26m)
      • 1 Stop PHL · Philadelphia 3h 26m
      • American Airlines (AA 5312)Canadair Regional
        American Airlines (AA 2095)Boeing 737 800
      • American Airlines (AA 5312)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 17:08 PWM
        22:05 ORD
        5Hrs, 57m 1 Stop (DCA)
      • PWMPortland Airport 17:08 - ORD 22:05 5h 57m 1 Stop (DCA) Washington
      • PWMPortland Airport 17:08
        DCAWashington Ronald Reagan National Airport 20:45
      • DCAWashington Ronald Reagan National Airport 19:15
        ORDChicago O'Hare International Airport 22:05
      • 5h 57m (1h 30m)
      • 1 Stop DCA · Washington 1h 30m
      • American Airlines (AA 4650)Embraer Emb 175
        American Airlines (AA 1630)Boeing 737 800
      • American Airlines (AA 4650)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 17:17 PWM
        22:05 ORD
        5Hrs, 48m 1 Stop (DCA)
      • PWMPortland Airport 17:17 - ORD 22:05 5h 48m 1 Stop (DCA) Washington
      • PWMPortland Airport 17:17
        DCAWashington Ronald Reagan National Airport 20:45
      • DCAWashington Ronald Reagan National Airport 19:15
        ORDChicago O'Hare International Airport 22:05
      • 5h 48m (1h 30m)
      • 1 Stop DCA · Washington 1h 30m
      • American Airlines (AA 1113)Airbus
        American Airlines (AA 1630)Boeing 737 800
      • American Airlines (AA 1113)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 18:15 PWM
        23:15 MDW
        6Hrs, 00m 1 Stop (BWI)
      • PWMPortland Airport 18:15 - MDW 23:15 6h 1 Stop (BWI) Baltimore
      • PWMPortland Airport 18:15
        BWIBaltimore Washington International Airport 22:10
      • BWIBaltimore Washington International Airport 19:55
        MDWChicago Midway Airport 23:15
      • 6h (2h 15m)
      • 1 Stop BWI · Baltimore 2h 15m
      • Southwest Airlines (WN 3053)Boeing 737 700
        Southwest Airlines (WN 2536)Boeing 737 700
      • Southwest Airlines (WN 3053)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 18:35 PWM
        23:10 MDW
        5Hrs, 35m 1 Stop (BWI)
      • PWMPortland Airport 18:35 - MDW 23:10 5h 35m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 18:35
        BWIBaltimore Washington International Airport 22:05
      • BWIBaltimore Washington International Airport 20:15
        MDWChicago Midway Airport 23:10
      • 5h 35m (1h 50m)
      • 1 Stop BWI · Baltimore 1h 50m
      • Southwest Airlines (WN 4468)Boeing 737 700
        Southwest Airlines (WN 724)Boeing 737 700
      • Southwest Airlines (WN 4468)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
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      What’s the fastest flight time from Portland to Chicago?

      The fastest flight time for direct flights from Portland to Chicago is 3 hours 12 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Portland to Chicago?

      The most popular airline flying from Portland to Chicago is United Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Portland?

      The flight distance between Portland and Chicago is 1429km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:20. The last flight of the day departs at 19:16. See the full list of flight times on Wego.

      How many airlines offer direct flights from Portland to Chicago?

      There are 1 airlines that offer direct flights from Portland to Chicago. Find out the list of airlines on Wego.

      All Airports in Portland

      Portland Airport PWM

      Popular Airlines Flying From Portland to Chicago

      United Airlines ‏()
      Southwest Airlines ‏()

      Popular Destinations From Chicago

      Popular Destinations From Portland

      Popular Hotels in Chicago

      Hotels In Popular Destinations