Cheap Flights from Portland, OR to Chicago, IL from $65

Return flight: Chicago – Portland
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On Cheapflightsplus.com you will find 1 connecting flights from Portland to Chicago. You can compare airfare deals from 1 airlines and multiple travel sites from $126, book and save on cheap plane tickets and last minute offers. Also check out PDX-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Portland to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $65 (one-way), $111 (round-trip).
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Best Flights from Portland to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Portland to Chicago with the lowest price of $126. Take a look at the list of flights with layovers from Portland to Chicago from $126. There’re no direct flights. The fastest connecting flight – 7h 1m.
Price Departure Arrival Flight Duration Airline Flight
from $126
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13:53
Portland
Portland
 22:54
Chicago
O'Hare International
 7h 1m
layover
0h 52m - Dallas
 American Airlines
AA2714
AA1294
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 28, 2023
Full flight schedule will help you in detecting at what time planes fly from Portland to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
13:53 — 22:54
13:53 — 19:38 AA2714 American Airlines
Portland — Dallas
52m stop
20:30 — 22:54 AA1294 American Airlines
Dallas — Chicago
7h 1m
including layover
Find flight
from$126
*Departure and arrival times - local. Updated on May 28, 2023

Flight Information

Below we will explain in detail what the flights cost on the destination from Portland to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Portland and Chicago is 2816 miles. Time difference between the cities is 2h. Airplanes depart 13:53 to 13:53 from 1 Portland airport and arrive 13:53 to 13:53 to 7 Chicago airports. Average flight time is 7h 1m.

  • The fastest flight 7h 1m
  • Average flight time 7h 1m
  • The earliest flight 13:53
  • The latest flight 13:53
  • Distance 1750 ml

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $126. This airfare is for economy class on one-way AA2714 flight by American Airlines for August 24, 2020 which leaves Portland in Portland at 13:53 am and arrives at Chicago O'Hare International at 22:54.

Economy class
$126
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Business class
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Popular Airlines on the Route

The flight Portland — Chicago is served by 1 regular airline . Most of the flights on this route are operated by American Airlines - 1 departures per week at the price of from $ 126 . And the most expensive tickets are offered by American Airlines airline - from $ 126.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 1 flights with layovers on the route. The fastest connecting flight is AA2714 by American Airlines takes 7h 1m and the cheapest is AA2714 by American Airlines for $126.

  • AA - American Airlines
    from $126
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Airports

You can fly from Portland to Chicago from 1 airports (Portland).

Portland airports

  • Portland-PDX
    from $126
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Airplanes

There are flights to Chicago from Portland by 1 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.

  • Boeing 737-800
    from $126
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Top Domestic Destinations from Portland

You may also consider searching for discounted plane tickets to some other popular places from Portland within United States.

Top International Destinations from Portland

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

All flights from Portland | All flights to Chicago

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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