$102 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 10/23. 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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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

Fri, Oct 24 - Fri, Oct 31
Multiple Airlines Logo
12:43 pm - 12:59 amPDX-ORD
10h 16m1 stop
Multiple Airlines Logo
2:05 pm - 4:41 pmORD-PDX
4h 36mnonstop
$193Multiple Airlines
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Sat, Nov 15 - Mon, Nov 17
Frontier Logo
12:52 pm - 11:29 pmPDX-ORD
8h 37m1 stop
Frontier Logo
6:20 pm - 11:56 amORD-PDX
19h 36m2 stops
$194Frontier
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Fri, Dec 5 - Mon, Dec 8
Delta Logo
12:32 am - 10:29 amPDX-ORD
7h 57m1 stop
Delta Logo
6:13 pm - 10:40 pmORD-PDX
6h 27m1 stop
$195Delta
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Fri, Oct 17 - Tue, Oct 21
Delta Logo
12:40 am - 10:30 amPDX-MDW
7h 50m1 stop
Delta Logo
1:48 pm - 8:26 pmMDW-PDX
8h 38m1 stop
$195Delta
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Wed, Oct 22 - Thu, Oct 30
Southwest Logo
6:15 am - 7:20 pmPDX-MDW
11h 05m1 stop
Southwest Logo
6:25 pm - 12:05 amMDW-PDX
7h 40m1 stop
$200Southwest
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Fri, Oct 31 - Wed, Nov 5
Alaska Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
Alaska Airlines Logo
2:54 pm - 8:46 pmORD-PDX
7h 52m1 stop
$201Alaska Airlines
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Wed, Oct 22 - Thu, Oct 30
Southwest Logo
1:25 pm - 7:20 pmPDX-MDW
3h 55mnonstop
Southwest Logo
7:50 am - 10:10 amMDW-PDX
4h 20mnonstop
$203Southwest
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Tue, Oct 21 - Fri, Oct 31
Alaska Airlines Logo
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
Alaska Airlines Logo
7:00 am - 9:39 amORD-PDX
4h 39mnonstop
$209Alaska Airlines
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Wed, Oct 15 - Mon, Oct 20
United Airlines Logo
3:50 pm - 12:54 amPDX-ORD
7h 04m1 stop
United Airlines Logo
7:15 am - 9:40 amORD-PDX
4h 25mnonstop
$213United Airlines
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Wed, Oct 15 - Mon, Oct 20
United Airlines Logo
1:09 pm - 10:39 pmMFR-ORD
7h 30m1 stop
United Airlines Logo
6:15 am - 12:07 pmORD-MFR
7h 52m1 stop
$223United Airlines
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Everything you should know

Cheapest round-trip
$193
Overall average: $353
Multiple Airlines
Fri 10/24Fri 10/31
PDX - ORD • 1 stop
Cheapest non-stop
$203
Typical prices: $284-516
United Airlines
Wed 10/15Mon 10/20
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$102
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Boise 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Munster
Chesterton
Schererville
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 $772
Business Class flights to Chicagofrom $573
Prem Econ Class flights to Chicagofrom $595
Economy Class flights to Chicagofrom $210

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