$89 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 1/9. 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
$216
Overall average: $489
Multiple Airlines
Tue 3/3Thu 3/12
BOI - ORD • 1 stop
Cheapest non-stop
$237
Typical prices: $231-$383
Alaska Airlines
Thu 1/22Sun 1/25
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 3 - Thu, Mar 12
Multiple Airlines Logo
7:00 am - 11:59 pm
BOI
-
ORD
15h 59m1 stop
Multiple Airlines Logo
7:00 am - 12:23 pm
ORD
-
BOI
6h 23m1 stop
$216Multiple Airlines
Tue, Jan 6 - Fri, Jan 9
Alaska Airlines Logo
6:00 pm - 2:38 pm
BOI
-
ORD
19h 38m1 stop
Alaska Airlines Logo
6:06 pm - 11:59 pm
ORD
-
BOI
6h 53m1 stop
$228Alaska Airlines
Thu, Jan 1 - Mon, Jan 5
Alaska Airlines Logo
11:00 pm - 5:02 am
PDX
-
ORD
4h 02mnonstop
Alaska Airlines Logo
3:37 pm - 10:04 pm
ORD
-
PDX
8h 27m1 stop
$236Alaska Airlines
Sat, Jan 17 - Tue, Jan 20
Southwest Logo
6:00 am - 11:55 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
4:10 pm - 10:30 pm
MDW
-
PDX
8h 20m1 stop
$237Southwest
Thu, Jan 15 - Mon, Jan 19
Delta Logo
12:37 pm - 9:52 pm
EUG
-
ORD
7h 15m1 stop
Delta Logo
6:40 pm - 11:59 pm
ORD
-
EUG
7h 19m1 stop
$239Delta
Fri, Jan 16 - Sun, Jan 18
Southwest Logo
6:45 am - 12:40 pm
PDX
-
MDW
3h 55mnonstop
Southwest Logo
11:10 am - 7:55 pm
MDW
-
PDX
10h 45m1 stop
$242Southwest
Thu, Jan 22 - Sat, Jan 31
United Airlines Logo
1:24 pm - 9:15 pm
PDX
-
ORD
5h 51m1 stop
United Airlines Logo
8:45 am - 2:46 pm
ORD
-
PDX
8h 01m1 stop
$242United Airlines
Tue, Dec 30 - Mon, Jan 5
United Airlines Logo
11:55 pm - 5:56 am
PDX
-
ORD
4h 01mnonstop
United Airlines Logo
7:58 pm - 10:40 pm
ORD
-
PDX
4h 42mnonstop
$243United Airlines
Thu, Jan 22 - Sat, Jan 31
Southwest Logo
2:15 pm - 10:50 pm
PDX
-
MDW
6h 35m1 stop
Southwest Logo
8:35 am - 2:35 pm
MDW
-
PDX
8h 00m1 stop
$246Southwest
Mon, Jan 5 - Sun, Jan 18
Delta Logo
9:45 pm - 8:43 am
PDX
-
ORD
8h 58m1 stop
Delta Logo
7:20 am - 12:32 pm
ORD
-
PDX
7h 12m1 stop
$247Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$89
Best time to beat the crowds with an average 16% 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 $992
Business Class flights to Chicagofrom $698
Prem Econ Class flights to Chicagofrom $616
Economy Class flights to Chicagofrom $184