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>

$85 CHEAP FLIGHTS from Oregon to Chicago

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

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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

Thu, Aug 21 - Sat, Aug 30

2:35 pm - 11:43 pmPDX-ORD

7h 08m1 stop

7:00 am - 10:39 pmORD-PDX

17h 39m1 stop

$171

Find Deal

Wed, Jul 9 - Mon, Jul 14

3:10 pm - 6:03 amPDX-ORD

12h 53m1 stop

7:08 am - 2:15 pmORD-PDX

9h 07m1 stop

$174Spirit Airlines

Find Deal

Sat, Sep 6 - Wed, Sep 10

5:50 pm - 11:59 pmPDX-ORD

4h 09mnonstop

2:07 pm - 4:36 pmORD-PDX

4h 29mnonstop

$181Alaska Airlines

Find Deal

Wed, Sep 3 - Wed, Sep 10

1:30 pm - 7:30 pmPDX-MDW

4h 00mnonstop

3:50 pm - 6:05 pmMDW-PDX

4h 15mnonstop

$181Southwest

Find Deal

Sat, Sep 6 - Tue, Sep 9

5:50 pm - 11:59 pmPDX-ORD

4h 09mnonstop

8:00 am - 12:24 pmORD-PDX

6h 24m1 stop

$191Alaska Airlines

Find Deal

Wed, Aug 20 - Tue, Aug 26

9:05 pm - 7:10 amPDX-MDW

8h 05m1 stop

8:30 pm - 10:45 pmMDW-PDX

4h 15mnonstop

$191Southwest

Find Deal

Fri, Oct 3 - Sat, Oct 11

11:30 pm - 8:34 amBOI-ORD

8h 04m1 stop

7:30 am - 4:29 pmORD-BOI

9h 59m1 stop

$195Delta

Find Deal

Sat, Jul 12 - Sat, Jul 19

5:40 am - 1:06 pmBOI-MDW

6h 26m1 stop

9:25 am - 5:05 pmMDW-BOI

8h 40m2 stops

$200Delta

Find Deal

Thu, Aug 14 - Sun, Aug 17

5:35 pm - 11:39 pmPDX-ORD

4h 04mnonstop

7:00 am - 9:25 amORD-PDX

4h 25mnonstop

$214Hawaiian Airlines

Find Deal

Fri, Sep 19 - Mon, Sep 22

8:37 pm - 7:03 amPDX-ORD

8h 26m1 stop

7:00 am - 9:25 amORD-PDX

4h 25mnonstop

$217Hawaiian Airlines

Find Deal

Useful Info

Low season	January
High season	August
Cheapest flight	$85

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 10% lower on average.

Flight from Portland 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.

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 $739

Business Class flights to Chicagofrom $915

Prem Econ Class flights to Chicagofrom $765

Economy Class flights to Chicagofrom $236

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

$85 Find Cheap Flights from Oregon to Chicago

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

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.

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