$71 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 12/7. 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, 0 bags

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Flight Deals

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

Thu, Jan 8 - Wed, Jan 14
Multiple Airlines Logo
12:35 pm - 9:01 pmEUG-ORD
30h 26m1 stop
Multiple Airlines Logo
6:40 am - 11:45 amORD-EUG
31h 05m2 stops
$220Multiple Airlines
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Wed, Dec 10 - Tue, Dec 16
Alaska Airlines Logo
2:31 pm - 11:50 pmPDX-ORD
7h 19m1 stop
Alaska Airlines Logo
2:05 pm - 4:48 pmORD-PDX
4h 43mnonstop
$227Alaska Airlines
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Fri, Nov 14 - Sat, Nov 15
Frontier Logo
3:26 pm - 12:15 amPDX-ORD
6h 49m1 stop
Frontier Logo
7:15 am - 11:56 amORD-PDX
6h 41m1 stop
$228Frontier
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Tue, Nov 11 - Fri, Nov 14
Frontier Logo
1:26 pm - 3:39 pmPDX-ORD
24h 13m1 stop
Frontier Logo
10:43 pm - 11:56 amORD-PDX
39h 13m2 stops
$229Frontier
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Wed, Jan 7 - Thu, Jan 15
American Airlines Logo
6:00 am - 12:15 pmPDX-ORD
4h 15mnonstop
American Airlines Logo
5:49 pm - 8:22 pmORD-PDX
4h 33mnonstop
$232American Airlines
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Tue, Mar 10 - Wed, Mar 11
Hawaiian Airlines Logo
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
Hawaiian Airlines Logo
7:45 am - 12:36 pmORD-PDX
6h 51m1 stop
$237Hawaiian Airlines
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Mon, Mar 9 - Wed, Mar 11
Delta Logo
12:55 am - 8:54 amPDX-MDW
5h 59m1 stop
Delta Logo
9:20 am - 4:51 pmMDW-PDX
9h 31m1 stop
$237Delta
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Sat, Dec 6 - Sat, Dec 13
Delta Logo
11:20 pm - 8:54 amPDX-MDW
7h 34m1 stop
Delta Logo
1:50 pm - 8:52 pmMDW-PDX
9h 02m1 stop
$238Delta
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Sun, Mar 1 - Tue, Mar 3
Hawaiian Airlines Logo
5:05 am - 1:04 pmMFR-ORD
5h 59m1 stop
Hawaiian Airlines Logo
10:00 am - 3:00 pmORD-MFR
7h 00m1 stop
$283Hawaiian Airlines
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Wed, Dec 10 - Sat, Dec 13
American Airlines Logo
2:57 pm - 12:31 amRDM-ORD
7h 34m1 stop
American Airlines Logo
12:10 pm - 7:33 pmORD-RDM
9h 23m1 stop
$298American Airlines
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Everything you should know

Cheapest round-trip
$220
Overall average: $383
Multiple Airlines
Thu 1/8Wed 1/14
EUG - ORD • 1 stop
Cheapest non-stop
$227
Typical prices: $331-$627
Alaska Airlines
Wed 12/10Mon 12/15
PDX - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$71
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Boise to Chicago Midway 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

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 $874
Business Class flights to Chicagofrom $877
Prem Econ Class flights to Chicagofrom $624
Economy Class flights to Chicagofrom $208

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