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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$65 CHEAP FLIGHTS from Oregon to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

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41,299,237 searches in the past 7 days on KAYAK

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Cheapest round-trip

$239

Overall average: $284

Frontier

Fri 1/9Sun 1/11

PDX - ORD • 2 stops

Cheapest non-stop

$243

Typical prices: $372-$570

Alaska Airlines

Tue 3/10Wed 3/11

PDX - ORD • Non-stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

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.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Oregon to Chicago

Fri, Jan 9 - Sun, Jan 11

10:29 am - 5:41 pmPDX-ORD

29h 12m2 stops

6:15 am - 4:16 pmORD-PDX

12h 01m1 stop

$239Frontier

Find Deal

Thu, Jan 8 - Sat, Jan 10

1:18 pm - 6:58 pmPDX-ORD

27h 40m1 stop

6:51 pm - 4:16 pmORD-PDX

23h 25m1 stop

$240Frontier

Find Deal

Sun, Dec 21 - Tue, Jan 6

11:00 pm - 5:02 amPDX-ORD

4h 02mnonstop

7:00 am - 9:50 amORD-PDX

4h 50mnonstop

$243Alaska Airlines

Find Deal

Thu, Nov 27 - Wed, Dec 3

11:10 am - 8:05 pmPDX-MDW

6h 55m1 stop

3:10 pm - 10:00 pmMDW-PDX

8h 50m1 stop

$243Southwest

Find Deal

Tue, Dec 2 - Tue, Dec 9

12:32 am - 8:40 amPDX-ORD

6h 08m1 stop

7:20 am - 12:40 pmORD-PDX

7h 20m1 stop

$244Delta

Find Deal

Thu, Nov 27 - Wed, Dec 3

11:53 am - 11:40 pmPDX-MDW

9h 47m1 stop

12:50 pm - 7:35 pmMDW-PDX

8h 45m1 stop

$244Delta

Find Deal

Mon, Dec 29 - Sun, Jan 4

11:00 pm - 5:02 amPDX-ORD

4h 02mnonstop

7:00 am - 9:50 amORD-PDX

4h 50mnonstop

$245Alaska Airlines

Find Deal

Sat, Jan 10 - Sat, Jan 17

6:00 am - 11:55 amPDX-MDW

3h 55mnonstop

8:35 am - 11:15 amMDW-PDX

4h 40mnonstop

$248Southwest

Find Deal

Mon, Dec 1 - Sat, Dec 6

5:15 pm - 6:25 amPDX-ORD

35h 10m2 stops

9:06 pm - 4:37 pmORD-PDX

21h 31m1 stop

$248Multiple Airlines

Find Deal

Tue, Dec 30 - Tue, Jan 6

12:47 pm - 12:12 amPDX-ORD

9h 25m1 stop

7:57 pm - 12:23 pmORD-PDX

42h 26m2 stops

$249Multiple Airlines

Find Deal

Useful Info

Low season	January
High season	July
Cheapest flight	$65

Best time to beat the crowds with an average 12% drop in price.

Most popular time to fly with an average 2% increase in price.

Flight from Boise to Chicago O'Hare Airport

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.

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

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Oregon

First Class flights to Chicagofrom $874

Business Class flights to Chicagofrom $698

Prem Econ Class flights to Chicagofrom $624

Economy Class flights to Chicagofrom $198

$65 Find Cheap Flights from Oregon to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Everything you should know

Cheap Flights from Oregon to Chicago

Recent round-trip flight deals from Oregon to Chicago

Recent one-way flight deals from Oregon to Chicago

Recent last minute flight deals from Oregon to Chicago

Recent direct flight deals from Oregon to Chicago

Good to know

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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Oregon

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight