$105 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 5/24. 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, Apr 23 - Sun, Apr 26
Frontier Logo
2:54 pm - 6:20 am
PDX
-
ORD
13h 26m
1 stop
Frontier Logo
8:58 pm - 8:59 am
ORD
-
PDX
14h 01m
1 stop
$250Frontier
Sat, May 9 - Sat, May 9
American Airlines Logo
6:22 am - 12:32 pm
PDX
-
ORD
4h 10mnonstop
American Airlines Logo
8:10 pm - 10:47 pm
ORD
-
PDX
4h 37mnonstop
$251American Airlines
Sat, May 9 - Sat, May 9
Southwest Logo
8:00 am - 1:55 pm
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
$251Southwest
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
2:54 pm - 6:20 am
PDX
-
ORD
13h 26m
1 stop
Frontier Logo
6:09 pm - 11:52 am
ORD
-
PDX
43h 43m
2 stops
$252Frontier
Tue, Apr 28 - Sat, May 2
Southwest Logo
11:20 am - 8:40 pm
EUG
-
MDW
7h 20m
1 stop
Southwest Logo
5:30 pm - 9:40 pm
MDW
-
EUG
6h 10m
1 stop
$257Southwest
Wed, Jun 10 - Tue, Jun 16
Delta Logo
6:13 am - 4:45 pm
EUG
-
ORD
8h 32m
1 stop
Delta Logo
7:37 pm - 11:58 pm
ORD
-
EUG
6h 21m
1 stop
$257Delta
Tue, May 5 - Wed, May 6
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
3:40 pm - 8:45 pm
MDW
-
PDX
7h 05m
1 stop
$257Southwest
Wed, Jun 10 - Tue, Sep 8
Delta Logo
6:13 am - 4:45 pm
EUG
-
ORD
8h 32m
1 stop
Delta Logo
1:35 pm - 11:54 pm
ORD
-
EUG
12h 19m
2 stops
$262Delta
Thu, Apr 30 - Wed, May 6
Alaska Airlines Logo
8:38 pm - 6:40 am
EUG
-
ORD
8h 02m
1 stop
Alaska Airlines Logo
3:52 pm - 10:54 pm
ORD
-
EUG
9h 02m
1 stop
$286Alaska Airlines
Tue, May 5 - Tue, May 12
Alaska Airlines Logo
5:56 pm - 1:13 pm
BOI
-
ORD
18h 17m
1 stop
Alaska Airlines Logo
8:50 am - 9:26 pm
ORD
-
BOI
13h 36m
1 stop
$295Alaska Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$105
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 6% 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
Griffith
Saint John

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.