Cheap Flights from Oregon to Chicago from $29

Q: 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!

Q: 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!

Q: 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!

Q: 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!

Good to know

Low season	January	Best time to beat the crowds with an average 3% drop in price.
High season	November	Most popular time to fly with an average 8% increase in price.
Average price of a round-trip	$357	(avg. price over the last 2 weeks)
Good deal for a round-trip	$159	or less

FAQs for booking Oregon to Chicago flights

How does KAYAK find such low prices 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?

What is the Hacker Fare option on flights from Oregon to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon to Chicago?

Top {4} airlines serving from Oregon to Chicago

Scores according to KAYAK customer reviews

8.0

Delta

Overall score based on 28,491 reviews

8.2

Boarding

7.8

Comfort

8.5

Crew

7.8

Entertainment

7.5

Food

Airline reviews

Book cheap flights from Oregon to Chicago (round-trip)

Airports

Origin

Destination

Multiple Airlines

Sat, Aug 29

9h 01m

Wed, Sep 9

9h 29m

$86

Trip: 12 days

Based on null reviews

Spirit Airlines

Sat, Aug 29

9h 01m

Sun, Sep 6

9h 48m

$103

Trip: 9 days

Based on null reviews

Multiple Airlines

Sat, Aug 29

9h 01m

Tue, Sep 8

9h 29m

$97

Trip: 11 days

Based on null reviews

Delta

Wed, Aug 12

9h 28m

Wed, Aug 19

12h 09m

$204

Trip: 8 days

Based on null reviews

Spirit Airlines

Sat, Aug 29

9h 01m

Sat, Sep 5

17h 02m

$106

Trip: 8 days

Based on null reviews

Multiple Airlines

Sat, Aug 29

9h 01m

Sat, Sep 5

17h 07m

$104

Trip: 8 days

Based on null reviews

Spirit Airlines

Fri, Jul 31

11h 11m

Sun, Aug 2

11h 32m

$110

Trip: 3 days

Based on null reviews

Multiple Airlines

Thu, Aug 6

14h 42m

Sat, Aug 8

12h 52m

$116

Trip: 3 days

Based on null reviews

Spirit Airlines

Sat, Aug 8

8h 00m

Mon, Aug 10

9h 48m

$117

Trip: 3 days

Based on null reviews

Multiple Airlines

Fri, Jul 31

7h 00m

Sat, Aug 15

12h 52m

$119

Trip: 16 days

Based on null reviews

Spirit Airlines

Thu, Jul 30

34h 25m

Sat, Aug 1

28h 33m

$122

Trip: 3 days

Based on null reviews

Multiple Airlines

Mon, Aug 10

7h 41m

Sun, Aug 16

24h 19m

$120

Trip: 7 days

Based on null reviews

Spirit Airlines

Fri, Jul 31

31h 19m

Mon, Aug 3

15h 17m

$125

Trip: 4 days

Based on null reviews

Multiple Airlines

Thu, Jul 30

34h 25m

Sat, Aug 1

14h 59m

$121

Trip: 3 days

Based on null reviews

Delta

Tue, Sep 15

8h 17m

Wed, Sep 23

7h 52m

$204

Trip: 9 days

Based on null reviews

Spirit Airlines

Sat, Aug 1

11h 11m

Mon, Aug 3

15h 17m

$128

Trip: 3 days

Based on null reviews

Multiple Airlines

Fri, Jul 31

7h 08m

Mon, Aug 3

11h 32m

$123

Trip: 4 days

Based on null reviews

Delta

Sat, Oct 24

22h 03m

Wed, Oct 28

12h 44m

$204

Trip: 5 days

Based on null reviews

Spirit Airlines

Mon, Jul 27

11h 11m

Tue, Jul 28

11h 32m

$129

Trip: 2 days

Based on null reviews

Multiple Airlines

Fri, Jul 31

7h 08m

Mon, Aug 3

11h 32m

$124

Trip: 4 days

Based on null reviews

Book cheap flights from Oregon to Chicago (one-way)

Airports

Origin

Destination

Spirit Airlines

Sat, Aug 1

11h 11m

$29

Based on null reviews

Multiple Airlines

Sat, Aug 15

14h 30m

$49

Based on null reviews

Spirit Airlines

Thu, Aug 6

9h 01m

$43

Based on null reviews

Multiple Airlines

Thu, Aug 6

14h 42m

$51

Based on null reviews

Delta

Sat, Aug 29

11h 02m

$102

Based on null reviews

Multiple Airlines

Wed, Jul 29

26h 45m

$55

Based on null reviews

Spirit Airlines

Mon, Aug 3

31h 19m

$56

Based on null reviews

Multiple Airlines

Mon, Aug 10

26h 51m

$57

Based on null reviews

Spirit Airlines

Sun, Aug 2

24h 50m

$59

Based on null reviews

Multiple Airlines

Mon, Aug 10

6h 48m

$58

Based on null reviews

Spirit Airlines

Tue, Aug 4

11h 11m

$64

Based on null reviews

Multiple Airlines

Fri, Jul 31

7h 00m

$60

Based on null reviews

Spirit Airlines

Sat, Aug 15

8h 00m

$65

Based on null reviews

Multiple Airlines

Mon, Aug 3

126h 48m

$62

Based on null reviews

Delta

Mon, Aug 17

12h 09m

$109

Based on null reviews

Multiple Airlines

Sun, Aug 2

33h 05m

$66

Based on null reviews

Spirit Airlines

Sat, Aug 8

8h 00m

$74

Based on null reviews

Major Airline

Sat, Aug 1

7h 03m

$239

Based on null reviews

Spirit Airlines

Fri, Jul 31

21h 11m

$75

Based on null reviews

Delta

Tue, Sep 8

7h 45m

$121

Based on null reviews

Flights to Chicago

Return flight deals:

Chicago - Oregon

Cabin classes:

First

$440

Business

$731

Prem Econ

$129

Economy

Browse origins:

$204

Eugene

$187

Medford

$765

North Bend

$80

Portland

$208

Redmond

Browse destinations:

$222

Chicago Midway Airport

$80

Chicago O'Hare Airport

Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Find cheap flights from Oregon to Chicago

Good to know

Low season

High season

Average price of a round-trip

Good deal for a round-trip

FAQs for booking Oregon to Chicago flights

How does KAYAK find such low prices 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?

What is the Hacker Fare option on flights from Oregon to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon to Chicago?

Top {4} airlines serving from Oregon to Chicago

Book cheap flights from Oregon to Chicago (round-trip)

Book cheap flights from Oregon to Chicago (one-way)

Flights to Chicago

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