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>

$97 CHEAP FLIGHTS from Oregon to Chicago

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

...and more

Travelers love KAYAK

41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$242

Overall average: $318

Frontier

Fri 2/6Sun 2/8

PDX - ORD • 2 stops

Cheapest non-stop

$243

Typical prices: $293-$428

Alaska Airlines

Mon 2/16Sat 2/21

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, Feb 6 - Sun, Feb 8

9:22 pm - 4:51 pmPDX-ORD

17h 29m2 stops

9:38 pm - 11:18 amORD-PDX

15h 40m1 stop

$242Frontier

Find Deal

Fri, Jan 9 - Sun, Jan 11

1:24 pm - 9:15 pmPDX-ORD

5h 51m1 stop

7:50 pm - 10:32 pmORD-PDX

4h 42mnonstop

$243United Airlines

Find Deal

Sun, Dec 21 - Sun, Dec 28

11:00 pm - 5:02 amPDX-ORD

4h 02mnonstop

2:12 pm - 4:50 pmORD-PDX

4h 38mnonstop

$246Alaska Airlines

Find Deal

Mon, Dec 29 - Thu, Jan 15

11:00 pm - 5:02 amPDX-ORD

4h 02mnonstop

3:35 pm - 8:47 pmORD-PDX

7h 12m1 stop

$247Alaska Airlines

Find Deal

Wed, Dec 31 - Mon, Jan 12

6:15 am - 5:19 pmPDX-MDW

9h 04m1 stop

1:49 pm - 8:12 pmMDW-PDX

8h 23m1 stop

$247Delta

Find Deal

Tue, Jan 27 - Sun, Feb 1

11:25 am - 9:50 pmPDX-MDW

8h 25m2 stops

8:10 am - 10:45 amMDW-PDX

4h 35mnonstop

$252Southwest

Find Deal

Sat, Jan 10 - Sat, Jan 17

6:10 am - 2:40 pmPDX-MDW

6h 30m1 stop

8:35 am - 11:15 amMDW-PDX

4h 40mnonstop

$253Southwest

Find Deal

Wed, Jan 14 - Tue, Jan 20

5:30 am - 5:55 pmEUG-ORD

10h 25m2 stops

6:40 pm - 11:59 pmORD-EUG

7h 19m1 stop

$256Delta

Find Deal

Thu, Jan 8 - Wed, Jan 14

3:18 pm - 7:59 pmBOI-ORD

3h 41mnonstop

10:43 am - 1:53 pmORD-BOI

4h 10mnonstop

$298American Airlines

Find Deal

Fri, Feb 6 - Mon, Feb 9

1:58 pm - 11:44 pmBOI-ORD

8h 46m1 stop

10:43 am - 1:53 pmORD-BOI

4h 10mnonstop

$305American Airlines

Find Deal

Useful Info

Low season	January
High season	November
Cheapest flight	$97

Best time to beat the crowds with an average 13% drop in price.

Most popular time to fly with an average 11% 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 $1,130

Business Class flights to Chicagofrom $698

Prem Econ Class flights to Chicagofrom $616

Economy Class flights to Chicagofrom $178

$97 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