$68 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 3/5. 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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Everything you should know

Cheapest round-trip
$159
Typical prices: $563-$1,009
Alaska Airlines
Tue 3/10Wed 3/11
EUG - ORD • 1 stop
Cheapest non-stop
$217
Typical prices: $240-$423
American Airlines
Sat 1/31Sat 2/14
PDX - ORD • Non-stop
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Flight Deals
Useful Info
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

Tue, Mar 10 - Wed, Mar 11
Alaska Airlines Logo
9:01 am - 11:56 pm
EUG
-
ORD
12h 55m1 stop
Alaska Airlines Logo
7:00 am - 9:31 pm
ORD
-
EUG
16h 31m1 stop
$159Alaska Airlines
Thu, Feb 5 - Mon, Feb 9
Delta Logo
5:20 pm - 11:53 pm
EUG
-
ORD
28h 33m1 stop
Delta Logo
2:20 pm - 10:48 am
ORD
-
EUG
22h 28m1 stop
$169Delta
Thu, Feb 5 - Sun, Feb 8
Delta Logo
6:10 am - 1:22 pm
EUG
-
ORD
29h 12m1 stop
Delta Logo
7:30 am - 10:48 am
ORD
-
EUG
29h 18m1 stop
$179Delta
Wed, Apr 1 - Mon, Apr 6
Southwest Logo
6:10 am - 4:40 pm
EUG
-
MDW
8h 30m2 stops
Southwest Logo
5:40 pm - 10:35 pm
MDW
-
EUG
6h 55m1 stop
$206Southwest
Tue, Apr 28 - Sat, May 2
Southwest Logo
5:20 pm - 5:00 am
EUG
-
MDW
9h 40m1 stop
Southwest Logo
6:15 am - 2:55 pm
MDW
-
EUG
10h 40m1 stop
$210Southwest
Fri, Jan 30 - Sun, Feb 1
American Airlines Logo
6:00 am - 12:15 pm
PDX
-
ORD
4h 15mnonstop
American Airlines Logo
5:49 pm - 8:22 pm
ORD
-
PDX
4h 33mnonstop
$219American Airlines
Thu, Mar 26 - Mon, Mar 30
Frontier Logo
8:53 am - 10:45 pm
PDX
-
MDW
11h 52m1 stop
Frontier Logo
10:36 pm - 8:58 am
MDW
-
PDX
12h 22m1 stop
$220Frontier
Sat, Feb 7 - Sat, Feb 14
United Airlines Logo
1:24 pm - 9:15 pm
PDX
-
ORD
5h 51m1 stop
United Airlines Logo
9:10 am - 11:55 am
ORD
-
PDX
4h 45mnonstop
$223United Airlines
Sat, Mar 7 - Mon, Mar 9
Frontier Logo
11:47 am - 10:41 pm
PDX
-
MDW
8h 54m1 stop
Frontier Logo
9:51 pm - 8:58 am
MDW
-
PDX
37h 07m2 stops
$225Frontier
Fri, Feb 13 - Tue, Feb 17
United Airlines Logo
11:59 pm - 5:53 am
PDX
-
ORD
3h 54mnonstop
United Airlines Logo
9:10 am - 11:55 am
ORD
-
PDX
4h 45mnonstop
$227United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 2% increase in price.
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
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 $788
Business Class flights to Chicagofrom $977
Prem Econ Class flights to Chicagofrom $659
Economy Class flights to Chicagofrom $217