Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Alaska Airlines

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

  • Alaska Airlines Alaska Airlines
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Spirit Airlines Spirit Airlines
Cheapest Month April

Travel Period: February 2025 - January 2026

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

  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
Cheapest Day of the Week Tuesday

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

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

Flight Schedules

Last Updated: Thu, 2 Jan, 2025

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      • 19:48 PDX
        05:30 ORD
        7Hrs, 42m 1 Stop (LAS)
      • PDXPortland Airport 19:48 - ORD 05:30 7h 42m 1 Stop (LAS) Las Vegas
      • PDXPortland Airport 19:48
        LASLas Vegas McCarran International Airport 23:58
      • LASLas Vegas McCarran International Airport 22:01
        ORDChicago O'Hare International Airport 05:30
      • 7h 42m (1h 57m)
      • 1 Stop LAS · Las Vegas 1h 57m
      • Spirit Airlines (NK 431)Airbus Industrie A320 Sharklets
        Spirit Airlines (NK 182)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 431)
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      • 13:05 PDX
        21:09 MDW
        6Hrs, 04m 1 Stop (DEN)
      • PDXPortland Airport 13:05 - MDW 21:09 6h 04m 1 Stop (DEN) Denver
      • PDXPortland Airport 13:05
        DENDenver Intl Airport 17:51
      • DENDenver Intl Airport 16:37
        MDWChicago Midway Airport 21:09
      • 6h 04m (1h 14m)
      • 1 Stop DEN · Denver 1h 14m
      • Frontier Airlines (F9 1790)Airbus A321 Neo
        Frontier Airlines (F9 2210)Airbus A320 Neo
      • Frontier Airlines (F9 1790)
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      • 13:05 PDX
        23:46 ORD
        8Hrs, 41m 1 Stop (DEN)
      • PDXPortland Airport 13:05 - ORD 23:46 8h 41m 1 Stop (DEN) Denver
      • PDXPortland Airport 13:05
        DENDenver Intl Airport 20:10
      • DENDenver Intl Airport 16:37
        ORDChicago O'Hare International Airport 23:46
      • 8h 41m (3h 33m)
      • 1 Stop DEN · Denver 3h 33m
      • Frontier Airlines (F9 1790)Airbus A321 Neo
        Frontier Airlines (F9 3172)Airbus A320 Neo
      • Frontier Airlines (F9 1790)
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      How far is Chicago from Portland?

      The flight distance between Portland and Chicago is 2823km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 13:05. The last flight of the day departs at 19:48. See the full list of flight times on Wego.

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      Portland Airport PDX

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