$64 Find Cheap Flights from Oregon to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Cheap Flights from Oregon to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oregon to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oregon to Chicago

Mon, Aug 4 - Sat, Aug 9
Frontier Logo
11:00 am - 9:06 pmPDX-ORD
8h 06m1 stop
Frontier Logo
7:00 am - 11:30 amORD-PDX
6h 30m1 stop
$131Frontier
Find Deal
Mon, Aug 4 - Sat, Aug 9
Frontier Logo
11:00 am - 9:06 pmPDX-ORD
8h 06m1 stop
Frontier Logo
7:00 am - 11:30 amORD-PDX
6h 30m1 stop
$132Frontier
Find Deal
Mon, Jul 28 - Tue, Jul 29
Logo
11:00 am - 9:06 pmPDX-ORD
8h 06m1 stop
Logo
7:08 am - 2:15 pmORD-PDX
9h 07m1 stop
$150
Find Deal
Mon, Jul 28 - Tue, Jul 29
Logo
11:00 am - 9:06 pmPDX-ORD
8h 06m1 stop
Logo
7:08 am - 2:15 pmORD-PDX
9h 07m1 stop
$155
Find Deal
Tue, Jul 22 - Tue, Jul 29
Spirit Airlines Logo
3:10 pm - 6:03 amPDX-ORD
12h 53m1 stop
Spirit Airlines Logo
7:08 am - 2:15 pmORD-PDX
9h 07m1 stop
$174Spirit Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
Spirit Airlines Logo
9:16 pm - 11:36 amBOI-ORD
13h 20m1 stop
Spirit Airlines Logo
10:15 am - 8:21 pmORD-BOI
11h 06m1 stop
$180Spirit Airlines
Find Deal
Sat, Aug 23 - Sun, Aug 31
Southwest Logo
9:55 am - 9:20 pmPDX-MDW
9h 25m1 stop
Southwest Logo
8:55 am - 11:10 amMDW-PDX
4h 15mnonstop
$213Southwest
Find Deal
Thu, Aug 28 - Sun, Aug 31
Southwest Logo
1:35 pm - 7:35 pmPDX-MDW
4h 00mnonstop
Southwest Logo
8:20 pm - 10:35 pmMDW-PDX
4h 15mnonstop
$214Southwest
Find Deal
Sat, Aug 30 - Tue, Sep 2
Hawaiian Airlines Logo
4:00 pm - 11:59 pmBOI-ORD
6h 59m1 stop
Hawaiian Airlines Logo
6:20 am - 3:00 pmORD-BOI
9h 40m1 stop
$214Hawaiian Airlines
Find Deal
Tue, Aug 5 - Wed, Aug 13
Hawaiian Airlines Logo
1:38 pm - 11:59 pmRDM-ORD
8h 21m1 stop
Hawaiian Airlines Logo
1:03 pm - 6:51 pmORD-RDM
7h 48m1 stop
$278Hawaiian Airlines
Find Deal
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$64
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Portland to Chicago O'Hare Airport

FAQs for booking flights from Oregon to Chicago

  • How does KAYAK find such low prices on flights from Oregon to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oregon to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oregon to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Oregon is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oregon to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Oregon with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Oregon

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $728
Business Class flights to Chicagofrom $1,079
Prem Econ Class flights to Chicagofrom $768
Economy Class flights to Chicagofrom $194

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