Take off on cheap flights from Portland to Chicago, your adventure starts now!

Find cheap airline tickets from Portland to Chicago by date

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • price
  • month of departure
  • month of return
$265
outward: Sep 28, 2018
7:05p PWM » 9:43p ORD
United Airlines direct (2h38m)
inbound: Sep 30, 2018
4:00p ORD » 6:18p PWM
United Airlines direct (2h18m)
$368
outward: Sep 26, 2018
7:05p PWM » 9:43p ORD
United Airlines direct (2h38m)
inbound: Oct 8, 2018
1:40p ORD » 5:59a PWM
Unknown Company 1 stop (16h19m)
Return
Departure
Choose when you'd like to depart to Chicago (USA):
Find the cheapest Portland Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Portland - Chicago with these new dates, click on an offer. Want to depart from another city? Choose: Las Vegas - Chicago New York - Chicago London - Chicago Miami - Chicago San Francisco - Chicago See more routes

Airlines operating flights from Portland to Chicago

Sorry! We haven't found any airline tickets from Portland to Chicago. Try launching another search above.

Travel tips for flights Portland - Chicago

Average flight duration: 2h38m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 21, 2018 8:10 PM, GMT-5
  • Weather:
  • min. 55ºF, max. 67ºF
  • Departure city:
  • Portland, USA
  • Airport(s):
  • Portland International Jetport (PWM)
  • Local time:
  • Sep 21, 2018 9:10 PM, GMT-4
  • Weather:
  • min. 48ºF, max. 67ºF