Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline United Airlines

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

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

Travel Period: December 2024 - November 2025

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

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Wednesday

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

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

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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      • Availability
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      • 09:30 PWM
        11:29 ORD
        2Hrs, 59m Direct
      • PWMPortland Airport 09:30 - ORD 11:29 2h 59m Direct
      • PWMPortland Airport 09:30
      • ORDChicago O'Hare International Airport 11:29
      • 2h 59m
      • Direct
      • United Airlines (UA 5570)Embraer 175
      • United Airlines (UA 5570)
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        • S
      • Embraer 175
      • 16:30 PWM
        18:42 ORD
        3Hrs, 12m Direct
      • PWMPortland Airport 16:30 - ORD 18:42 3h 12m Direct
      • PWMPortland Airport 16:30
      • ORDChicago O'Hare International Airport 18:42
      • 3h 12m
      • Direct
      • United Airlines (UA 3678)Embraer 175
      • United Airlines (UA 3678)
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        • S
      • Embraer 175
      • 19:27 PWM
        23:20 ORD
        4Hrs, 53m 1 Stop (IAD)
      • PWMPortland Airport 19:27 - ORD 23:20 4h 53m 1 Stop (IAD) Washington
      • PWMPortland Airport 19:27
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 4h 53m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 3582)Embraer 170
        United Airlines (UA 1738)Airbus
      • United Airlines (UA 3582)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 19:27 PWM
        23:20 ORD
        4Hrs, 53m 1 Stop (IAD)
      • PWMPortland Airport 19:27 - ORD 23:20 4h 53m 1 Stop (IAD) Washington
      • PWMPortland Airport 19:27
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 4h 53m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 3582)Embraer 170
        United Airlines (UA 1738)Boeing 737 800
      • United Airlines (UA 3582)
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        • -
        • -
      • 19:27 PWM
        23:20 ORD
        4Hrs, 53m 1 Stop (IAD)
      • PWMPortland Airport 19:27 - ORD 23:20 4h 53m 1 Stop (IAD) Washington
      • PWMPortland Airport 19:27
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 4h 53m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 3582)Embraer 175
        United Airlines (UA 1738)Boeing 737 800
      • United Airlines (UA 3582)
        • -
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        • -
        • -
        • -
      • 19:27 PWM
        23:20 ORD
        4Hrs, 53m 1 Stop (IAD)
      • PWMPortland Airport 19:27 - ORD 23:20 4h 53m 1 Stop (IAD) Washington
      • PWMPortland Airport 19:27
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 4h 53m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 3582)Embraer 170
        United Airlines (UA 1738)Boeing 737 700
      • United Airlines (UA 3582)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:27 PWM
        23:20 ORD
        4Hrs, 53m 1 Stop (IAD)
      • PWMPortland Airport 19:27 - ORD 23:20 4h 53m 1 Stop (IAD) Washington
      • PWMPortland Airport 19:27
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 4h 53m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 3582)Embraer 170
        United Airlines (UA 1738)Boeing 737 900
      • United Airlines (UA 3582)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 05:20 PWM
        11:20 MDW
        7Hrs, 00m 1 Stop (BWI)
      • PWMPortland Airport 05:20 - MDW 11:20 7h 1 Stop (BWI) Baltimore
      • PWMPortland Airport 05:20
        BWIBaltimore Washington International Airport 10:15
      • BWIBaltimore Washington International Airport 07:05
        MDWChicago Midway Airport 11:20
      • 7h (3h 10m)
      • 1 Stop BWI · Baltimore 3h 10m
      • Southwest Airlines (WN 429)Boeing 737 800
        Southwest Airlines (WN 5265)Boeing 737 700
      • Southwest Airlines (WN 429)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:22 PWM
        10:58 ORD
        6Hrs, 36m 1 Stop (DCA)
      • PWMPortland Airport 05:22 - ORD 10:58 6h 36m 1 Stop (DCA) Washington
      • PWMPortland Airport 05:22
        DCAWashington Ronald Reagan National Airport 09:44
      • DCAWashington Ronald Reagan National Airport 07:31
        ORDChicago O'Hare International Airport 10:58
      • 6h 36m (2h 13m)
      • 1 Stop DCA · Washington 2h 13m
      • American Airlines (AA 5657)Canadair Regional
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 5657)
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      • 05:22 PWM
        11:00 ORD
        6Hrs, 38m 1 Stop (DCA)
      • PWMPortland Airport 05:22 - ORD 11:00 6h 38m 1 Stop (DCA) Washington
      • PWMPortland Airport 05:22
        DCAWashington Ronald Reagan National Airport 09:44
      • DCAWashington Ronald Reagan National Airport 07:31
        ORDChicago O'Hare International Airport 11:00
      • 6h 38m (2h 13m)
      • 1 Stop DCA · Washington 2h 13m
      • American Airlines (AA 5657)Canadair Regional
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 5657)
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      • 05:22 PWM
        11:01 ORD
        6Hrs, 39m 1 Stop (DCA)
      • PWMPortland Airport 05:22 - ORD 11:01 6h 39m 1 Stop (DCA) Washington
      • PWMPortland Airport 05:22
        DCAWashington Ronald Reagan National Airport 09:45
      • DCAWashington Ronald Reagan National Airport 07:31
        ORDChicago O'Hare International Airport 11:01
      • 6h 39m (2h 14m)
      • 1 Stop DCA · Washington 2h 14m
      • American Airlines (AA 5657)Canadair Regional
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 5657)
        • -
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        • -
        • -
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        • S
        • -
      • 05:30 PWM
        09:29 ORD
        4Hrs, 59m 1 Stop (IAD)
      • PWMPortland Airport 05:30 - ORD 09:29 4h 59m 1 Stop (IAD) Washington
      • PWMPortland Airport 05:30
        IADWashington Dulles International Airport 08:15
      • IADWashington Dulles International Airport 07:18
        ORDChicago O'Hare International Airport 09:29
      • 4h 59m (57m)
      • 1 Stop IAD · Washington 57m
      • United Airlines (UA 1172)Airbus
        United Airlines (UA 672)Boeing 737 800
      • United Airlines (UA 1172)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:30 PWM
        09:49 ORD
        5Hrs, 19m 1 Stop (IAD)
      • PWMPortland Airport 05:30 - ORD 09:49 5h 19m 1 Stop (IAD) Washington
      • PWMPortland Airport 05:30
        IADWashington Dulles International Airport 08:35
      • IADWashington Dulles International Airport 07:18
        ORDChicago O'Hare International Airport 09:49
      • 5h 19m (1h 17m)
      • 1 Stop IAD · Washington 1h 17m
      • United Airlines (UA 1172)Airbus
        United Airlines (UA 672)Boeing 737 800
      • United Airlines (UA 1172)
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        • F
        • -
        • -
      • 05:30 PWM
        10:40 MDW
        6Hrs, 10m 1 Stop (BWI)
      • PWMPortland Airport 05:30 - MDW 10:40 6h 10m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 05:30
        BWIBaltimore Washington International Airport 09:35
      • BWIBaltimore Washington International Airport 07:15
        MDWChicago Midway Airport 10:40
      • 6h 10m (2h 20m)
      • 1 Stop BWI · Baltimore 2h 20m
      • Southwest Airlines (WN 429)Boeing 737 800
        Southwest Airlines (WN 5265)Boeing 737 700
      • Southwest Airlines (WN 429)
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      • 05:50 PWM
        11:13 ORD
        6Hrs, 23m 1 Stop (PHL)
      • PWMPortland Airport 05:50 - ORD 11:13 6h 23m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 05:50
        PHLPhiladelphia International Airport 09:42
      • PHLPhiladelphia International Airport 07:40
        ORDChicago O'Hare International Airport 11:13
      • 6h 23m (2h 02m)
      • 1 Stop PHL · Philadelphia 2h 02m
      • American Airlines (AA 5043)Canadair Regional
        American Airlines (AA 2095)Boeing 737 800
      • American Airlines (AA 5043)
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        • S
      • 05:50 PWM
        12:24 ORD
        7Hrs, 34m 1 Stop (PHL)
      • PWMPortland Airport 05:50 - ORD 12:24 7h 34m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 05:50
        PHLPhiladelphia International Airport 10:46
      • PHLPhiladelphia International Airport 07:40
        ORDChicago O'Hare International Airport 12:24
      • 7h 34m (3h 06m)
      • 1 Stop PHL · Philadelphia 3h 06m
      • American Airlines (AA 5043)Canadair Regional
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 5043)
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        • -
      • 05:50 PWM
        12:25 ORD
        7Hrs, 35m 1 Stop (PHL)
      • PWMPortland Airport 05:50 - ORD 12:25 7h 35m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 05:50
        PHLPhiladelphia International Airport 10:46
      • PHLPhiladelphia International Airport 07:40
        ORDChicago O'Hare International Airport 12:25
      • 7h 35m (3h 06m)
      • 1 Stop PHL · Philadelphia 3h 06m
      • American Airlines (AA 5043)Canadair Regional
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 5043)
        • M
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      • 06:00 PWM
        10:44 ORD
        5Hrs, 44m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 10:44 5h 44m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 09:00
      • EWRNewark Liberty International Airport 07:34
        ORDChicago O'Hare International Airport 10:44
      • 5h 44m (1h 26m)
      • 1 Stop EWR · New York City 1h 26m
      • United Airlines (UA 2455)Boeing 737 Max 8 Passenger
        United Airlines (UA 2290)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2455)
        • -
        • -
        • -
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      • 06:00 PWM
        10:44 ORD
        5Hrs, 44m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 10:44 5h 44m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 09:00
      • EWRNewark Liberty International Airport 07:34
        ORDChicago O'Hare International Airport 10:44
      • 5h 44m (1h 26m)
      • 1 Stop EWR · New York City 1h 26m
      • United Airlines (UA 2455)Airbus
        United Airlines (UA 2290)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2455)
        • -
        • -
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        • S
      • 06:00 PWM
        10:44 ORD
        5Hrs, 44m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 10:44 5h 44m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 09:00
      • EWRNewark Liberty International Airport 07:34
        ORDChicago O'Hare International Airport 10:44
      • 5h 44m (1h 26m)
      • 1 Stop EWR · New York City 1h 26m
      • United Airlines (UA 2455)Boeing 737 Max 8 Passenger
        United Airlines (UA 2290)Boeing 737 900
      • United Airlines (UA 2455)
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      • 06:00 PWM
        11:46 ORD
        6Hrs, 46m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 11:46 6h 46m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 10:15
      • EWRNewark Liberty International Airport 07:34
        ORDChicago O'Hare International Airport 11:46
      • 6h 46m (2h 41m)
      • 1 Stop EWR · New York City 2h 41m
      • United Airlines (UA 2455)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 2455)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:00 PWM
        12:04 ORD
        7Hrs, 04m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 12:04 7h 04m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 10:30
      • EWRNewark Liberty International Airport 07:34
        ORDChicago O'Hare International Airport 12:04
      • 7h 04m (2h 56m)
      • 1 Stop EWR · New York City 2h 56m
      • United Airlines (UA 2455)Airbus
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 2455)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 PWM
        12:04 ORD
        7Hrs, 04m 1 Stop (EWR)
      • PWMPortland Airport 06:00 - ORD 12:04 7h 04m 1 Stop (EWR) New York City
      • PWMPortland Airport 06:00
        EWRNewark Liberty International Airport 10:30
      • EWRNewark Liberty International Airport 07:34
        ORDChicago O'Hare International Airport 12:04
      • 7h 04m (2h 56m)
      • 1 Stop EWR · New York City 2h 56m
      • United Airlines (UA 2455)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 2455)
        • M
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        • -
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        • -
      • 07:18 PWM
        12:15 ORD
        5Hrs, 57m 1 Stop (CLT)
      • PWMPortland Airport 07:18 - ORD 12:15 5h 57m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 07:18
        CLTCharlotte Airport 11:10
      • CLTCharlotte Airport 10:00
        ORDChicago O'Hare International Airport 12:15
      • 5h 57m (1h 10m)
      • 1 Stop CLT · Charlotte 1h 10m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 2981)
        • M
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        • F
        • -
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      • 07:18 PWM
        12:24 ORD
        6Hrs, 06m 1 Stop (CLT)
      • PWMPortland Airport 07:18 - ORD 12:24 6h 06m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 07:18
        CLTCharlotte Airport 11:13
      • CLTCharlotte Airport 10:00
        ORDChicago O'Hare International Airport 12:24
      • 6h 06m (1h 13m)
      • 1 Stop CLT · Charlotte 1h 13m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 2981)
        • -
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        • -
        • -
        • -
        • -
      • 07:18 PWM
        13:10 ORD
        6Hrs, 52m 1 Stop (CLT)
      • PWMPortland Airport 07:18 - ORD 13:10 6h 52m 1 Stop (CLT) Charlotte
      • PWMPortland Airport 07:18
        CLTCharlotte Airport 11:40
      • CLTCharlotte Airport 10:00
        ORDChicago O'Hare International Airport 13:10
      • 6h 52m (1h 40m)
      • 1 Stop CLT · Charlotte 1h 40m
      • American Airlines (AA 2981)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 2981)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 09:40 PWM
        14:19 ORD
        5Hrs, 39m 1 Stop (IAD)
      • PWMPortland Airport 09:40 - ORD 14:19 5h 39m 1 Stop (IAD) Washington
      • PWMPortland Airport 09:40
        IADWashington Dulles International Airport 13:05
      • IADWashington Dulles International Airport 11:35
        ORDChicago O'Hare International Airport 14:19
      • 5h 39m (1h 30m)
      • 1 Stop IAD · Washington 1h 30m
      • United Airlines (UA 6210)Embraer 175
        United Airlines (UA 673)Boeing 737 800
      • United Airlines (UA 6210)
        • M
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        • W
        • T
        • F
        • S
        • -
      • 09:40 PWM
        14:19 ORD
        5Hrs, 39m 1 Stop (IAD)
      • PWMPortland Airport 09:40 - ORD 14:19 5h 39m 1 Stop (IAD) Washington
      • PWMPortland Airport 09:40
        IADWashington Dulles International Airport 13:05
      • IADWashington Dulles International Airport 11:35
        ORDChicago O'Hare International Airport 14:19
      • 5h 39m (1h 30m)
      • 1 Stop IAD · Washington 1h 30m
      • United Airlines (UA 6210)Embraer 175
        United Airlines (UA 673)Boeing 737 700
      • United Airlines (UA 6210)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 11:24 PWM
        15:43 ORD
        5Hrs, 19m 1 Stop (EWR)
      • PWMPortland Airport 11:24 - ORD 15:43 5h 19m 1 Stop (EWR) New York City
      • PWMPortland Airport 11:24
        EWRNewark Liberty International Airport 14:09
      • EWRNewark Liberty International Airport 13:00
        ORDChicago O'Hare International Airport 15:43
      • 5h 19m (1h 09m)
      • 1 Stop EWR · New York City 1h 09m
      • United Airlines (UA 3623)Embraer 175
        United Airlines (UA 645)Boeing 737 900
      • United Airlines (UA 3623)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 11:24 PWM
        15:48 ORD
        5Hrs, 24m 1 Stop (EWR)
      • PWMPortland Airport 11:24 - ORD 15:48 5h 24m 1 Stop (EWR) New York City
      • PWMPortland Airport 11:24
        EWRNewark Liberty International Airport 14:14
      • EWRNewark Liberty International Airport 13:00
        ORDChicago O'Hare International Airport 15:48
      • 5h 24m (1h 14m)
      • 1 Stop EWR · New York City 1h 14m
      • United Airlines (UA 3623)Embraer 175
        United Airlines (UA 645)Boeing 737 Max 9 Passenger
      • United Airlines (UA 3623)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 11:24 PWM
        16:54 ORD
        6Hrs, 30m 1 Stop (EWR)
      • PWMPortland Airport 11:24 - ORD 16:54 6h 30m 1 Stop (EWR) New York City
      • PWMPortland Airport 11:24
        EWRNewark Liberty International Airport 15:15
      • EWRNewark Liberty International Airport 13:00
        ORDChicago O'Hare International Airport 16:54
      • 6h 30m (2h 15m)
      • 1 Stop EWR · New York City 2h 15m
      • United Airlines (UA 3623)Embraer 175
        United Airlines (UA 1144)Boeing 757 200 Series
      • United Airlines (UA 3623)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 11:25 PWM
        15:43 ORD
        5Hrs, 18m 1 Stop (EWR)
      • PWMPortland Airport 11:25 - ORD 15:43 5h 18m 1 Stop (EWR) New York City
      • PWMPortland Airport 11:25
        EWRNewark Liberty International Airport 14:09
      • EWRNewark Liberty International Airport 13:01
        ORDChicago O'Hare International Airport 15:43
      • 5h 18m (1h 08m)
      • 1 Stop EWR · New York City 1h 08m
      • United Airlines (UA 3623)Embraer 175
        United Airlines (UA 645)Boeing 737 900
      • United Airlines (UA 3623)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:25 PWM
        16:54 ORD
        6Hrs, 29m 1 Stop (EWR)
      • PWMPortland Airport 11:25 - ORD 16:54 6h 29m 1 Stop (EWR) New York City
      • PWMPortland Airport 11:25
        EWRNewark Liberty International Airport 15:15
      • EWRNewark Liberty International Airport 13:01
        ORDChicago O'Hare International Airport 16:54
      • 6h 29m (2h 14m)
      • 1 Stop EWR · New York City 2h 14m
      • United Airlines (UA 3623)Embraer 175
        United Airlines (UA 1144)Boeing 757 200 Series
      • United Airlines (UA 3623)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:24 PWM
        16:07 ORD
        4Hrs, 43m 1 Stop (DCA)
      • PWMPortland Airport 12:24 - ORD 16:07 4h 43m 1 Stop (DCA) Washington
      • PWMPortland Airport 12:24
        DCAWashington Ronald Reagan National Airport 14:49
      • DCAWashington Ronald Reagan National Airport 14:19
        ORDChicago O'Hare International Airport 16:07
      • 4h 43m (30m)
      • 1 Stop DCA · Washington 30m
      • American Airlines (AA 5056)Crj 700 Canadair Regional
        American Airlines (AA 1682)Boeing 737 800
      • American Airlines (AA 5056)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 12:24 PWM
        16:09 ORD
        4Hrs, 45m 1 Stop (DCA)
      • PWMPortland Airport 12:24 - ORD 16:09 4h 45m 1 Stop (DCA) Washington
      • PWMPortland Airport 12:24
        DCAWashington Ronald Reagan National Airport 14:49
      • DCAWashington Ronald Reagan National Airport 14:19
        ORDChicago O'Hare International Airport 16:09
      • 4h 45m (30m)
      • 1 Stop DCA · Washington 30m
      • American Airlines (AA 5056)Crj 700 Canadair Regional
        American Airlines (AA 1682)Boeing 737 800
      • American Airlines (AA 5056)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 17:32 DTW
        14:24 DCA
        6Hrs, 25m 1 Stop (ORD)
      • DTWDetroit Wayne County 17:32 - DCA 14:24 6h 25m 1 Stop (ORD) Chicago
      • DTWDetroit Wayne County 17:32
        PWMPortland Airport 12:30
      • ORDChicago O'Hare International Airport 17:55
        DCAWashington Ronald Reagan National Airport 14:24
      • 6h 25m (1h 13m)
      • 1 Stop ORD · Chicago 1h 13m
      • American Airlines (AA 3288)Airbus
        American Airlines (AA 5652)Canadair Regional
      • American Airlines (AA 3288)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 12:30 PWM
        19:17 ORD
        7Hrs, 47m 1 Stop (DCA)
      • PWMPortland Airport 12:30 - ORD 19:17 7h 47m 1 Stop (DCA) Washington
      • PWMPortland Airport 12:30
        DCAWashington Ronald Reagan National Airport 17:59
      • DCAWashington Ronald Reagan National Airport 14:24
        ORDChicago O'Hare International Airport 19:17
      • 7h 47m (3h 35m)
      • 1 Stop DCA · Washington 3h 35m
      • American Airlines (AA 5652)Canadair Regional
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 5652)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 12:30 PWM
        19:19 ORD
        7Hrs, 49m 1 Stop (DCA)
      • PWMPortland Airport 12:30 - ORD 19:19 7h 49m 1 Stop (DCA) Washington
      • PWMPortland Airport 12:30
        DCAWashington Ronald Reagan National Airport 17:59
      • DCAWashington Ronald Reagan National Airport 14:24
        ORDChicago O'Hare International Airport 19:19
      • 7h 49m (3h 35m)
      • 1 Stop DCA · Washington 3h 35m
      • American Airlines (AA 5652)Canadair Regional
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 5652)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 12:55 PWM
        18:40 MDW
        6Hrs, 45m 1 Stop (BWI)
      • PWMPortland Airport 12:55 - MDW 18:40 6h 45m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 12:55
        BWIBaltimore Washington International Airport 17:35
      • BWIBaltimore Washington International Airport 14:35
        MDWChicago Midway Airport 18:40
      • 6h 45m (3h)
      • 1 Stop BWI · Baltimore 3h
      • Southwest Airlines (WN 2258)Boeing 737 800
        Southwest Airlines (WN 981)Boeing 737 800
      • Southwest Airlines (WN 2258)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:59 PWM
        17:31 ORD
        5Hrs, 32m 1 Stop (PHL)
      • PWMPortland Airport 12:59 - ORD 17:31 5h 32m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 12:59
        PHLPhiladelphia International Airport 16:00
      • PHLPhiladelphia International Airport 14:48
        ORDChicago O'Hare International Airport 17:31
      • 5h 32m (1h 12m)
      • 1 Stop PHL · Philadelphia 1h 12m
      • American Airlines (AA 4520)Embraer Emb 175
        American Airlines (AA 1090)Boeing 737 800
      • American Airlines (AA 4520)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 12:59 PWM
        17:32 ORD
        5Hrs, 33m 1 Stop (PHL)
      • PWMPortland Airport 12:59 - ORD 17:32 5h 33m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 12:59
        PHLPhiladelphia International Airport 16:00
      • PHLPhiladelphia International Airport 14:48
        ORDChicago O'Hare International Airport 17:32
      • 5h 33m (1h 12m)
      • 1 Stop PHL · Philadelphia 1h 12m
      • American Airlines (AA 4520)Embraer Emb 175
        American Airlines (AA 1090)Boeing 737 800
      • American Airlines (AA 4520)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 12:59 PWM
        19:45 ORD
        7Hrs, 46m 1 Stop (PHL)
      • PWMPortland Airport 12:59 - ORD 19:45 7h 46m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 12:59
        PHLPhiladelphia International Airport 18:13
      • PHLPhiladelphia International Airport 14:48
        ORDChicago O'Hare International Airport 19:45
      • 7h 46m (3h 25m)
      • 1 Stop PHL · Philadelphia 3h 25m
      • American Airlines (AA 4520)Embraer Emb 175
        American Airlines (AA 490)Airbus
      • American Airlines (AA 4520)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 13:06 PWM
        17:32 ORD
        5Hrs, 26m 1 Stop (PHL)
      • PWMPortland Airport 13:06 - ORD 17:32 5h 26m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 13:06
        PHLPhiladelphia International Airport 16:00
      • PHLPhiladelphia International Airport 14:44
        ORDChicago O'Hare International Airport 17:32
      • 5h 26m (1h 16m)
      • 1 Stop PHL · Philadelphia 1h 16m
      • American Airlines (AA 5249)Canadair Regional
        American Airlines (AA 1090)Boeing 737 800
      • American Airlines (AA 5249)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 13:06 PWM
        17:36 ORD
        5Hrs, 30m 1 Stop (PHL)
      • PWMPortland Airport 13:06 - ORD 17:36 5h 30m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 13:06
        PHLPhiladelphia International Airport 16:06
      • PHLPhiladelphia International Airport 14:44
        ORDChicago O'Hare International Airport 17:36
      • 5h 30m (1h 22m)
      • 1 Stop PHL · Philadelphia 1h 22m
      • American Airlines (AA 5020)Canadair Regional
        American Airlines (AA 1090)Airbus
      • American Airlines (AA 5020)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:06 PWM
        19:45 ORD
        7Hrs, 39m 1 Stop (PHL)
      • PWMPortland Airport 13:06 - ORD 19:45 7h 39m 1 Stop (PHL) Philadelphia
      • PWMPortland Airport 13:06
        PHLPhiladelphia International Airport 18:13
      • PHLPhiladelphia International Airport 14:44
        ORDChicago O'Hare International Airport 19:45
      • 7h 39m (3h 29m)
      • 1 Stop PHL · Philadelphia 3h 29m
      • American Airlines (AA 5020)Canadair Regional
        American Airlines (AA 490)Airbus
      • American Airlines (AA 5020)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 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
        • -
        • -
        • -
        • -
      • 13:31 PWM
        18:35 ORD
        6Hrs, 04m 1 Stop (IAD)
      • PWMPortland Airport 13:31 - ORD 18:35 6h 04m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:31
        IADWashington Dulles International Airport 17:21
      • IADWashington Dulles International Airport 15:30
        ORDChicago O'Hare International Airport 18:35
      • 6h 04m (1h 51m)
      • 1 Stop IAD · Washington 1h 51m
      • United Airlines (UA 6062)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 6062)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 13:31 PWM
        18:35 ORD
        6Hrs, 04m 1 Stop (IAD)
      • PWMPortland Airport 13:31 - ORD 18:35 6h 04m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:31
        IADWashington Dulles International Airport 17:21
      • IADWashington Dulles International Airport 15:30
        ORDChicago O'Hare International Airport 18:35
      • 6h 04m (1h 51m)
      • 1 Stop IAD · Washington 1h 51m
      • United Airlines (UA 6062)Embraer 175
        United Airlines (UA 2497)Boeing 737 800
      • United Airlines (UA 6062)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 13:31 PWM
        18:35 ORD
        6Hrs, 04m 1 Stop (IAD)
      • PWMPortland Airport 13:31 - ORD 18:35 6h 04m 1 Stop (IAD) Washington
      • PWMPortland Airport 13:31
        IADWashington Dulles International Airport 17:21
      • IADWashington Dulles International Airport 15:33
        ORDChicago O'Hare International Airport 18:35
      • 6h 04m (1h 48m)
      • 1 Stop IAD · Washington 1h 48m
      • United Airlines (UA 4376)Embraer
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 4376)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:37 PWM
        19:17 ORD
        6Hrs, 40m 1 Stop (DCA)
      • PWMPortland Airport 13:37 - ORD 19:17 6h 40m 1 Stop (DCA) Washington
      • PWMPortland Airport 13:37
        DCAWashington Ronald Reagan National Airport 17:59
      • DCAWashington Ronald Reagan National Airport 15:34
        ORDChicago O'Hare International Airport 19:17
      • 6h 40m (2h 25m)
      • 1 Stop DCA · Washington 2h 25m
      • American Airlines (AA 5469)Crj 700 Canadair Regional
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 5469)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 13:37 PWM
        19:19 ORD
        6Hrs, 42m 1 Stop (DCA)
      • PWMPortland Airport 13:37 - ORD 19:19 6h 42m 1 Stop (DCA) Washington
      • PWMPortland Airport 13:37
        DCAWashington Ronald Reagan National Airport 17:59
      • DCAWashington Ronald Reagan National Airport 15:34
        ORDChicago O'Hare International Airport 19:19
      • 6h 42m (2h 25m)
      • 1 Stop DCA · Washington 2h 25m
      • American Airlines (AA 5469)Crj 700 Canadair Regional
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 5469)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 15:10 PWM
        19:35 MDW
        5Hrs, 25m 1 Stop (BWI)
      • PWMPortland Airport 15:10 - MDW 19:35 5h 25m 1 Stop (BWI) Baltimore
      • PWMPortland Airport 15:10
        BWIBaltimore Washington International Airport 18:30
      • BWIBaltimore Washington International Airport 16:50
        MDWChicago Midway Airport 19:35
      • 5h 25m (1h 40m)
      • 1 Stop BWI · Baltimore 1h 40m
      • Southwest Airlines (WN 3053)Boeing 737 700
        Southwest Airlines (WN 1776)Boeing 737 800
      • Southwest Airlines (WN 3053)
        • M
        • -
        • -
        • T
        • F
        • -
        • 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 2 hours 59 minutes. Check latest flight schedules & prices 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 19:27. 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.

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