Find cheap flights from Oregon to Chicago

Find cheap flights from Oregon to Chicago

Round-trip
Economy
Boston (BOS)
Chicago All airports
Fri 7/31
Fri 8/7
Any month
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Search hundreds of travel sites at once for deals on flights to Chicago

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
Read more about Delta

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

Airports
Origin
Portland
$86
only
$86
Redmond
$204
only
$204
Medford
$204
only
$204
Destination
Chicago
$86
only
$86
$204
only
$204
Sat, Aug 29
PDX
Portland Airport
ORD
Chicago O'Hare Airport
9h 01m
Wed, Sep 9
ORD
Chicago O'Hare Airport
PDX
Portland Airport
9h 29m
Trip: 12 days
Based on null reviews
Sat, Aug 29
PDX
Portland Airport
ORD
Chicago O'Hare Airport
9h 01m
Sun, Sep 6
ORD
Chicago O'Hare Airport
PDX
Portland Airport
9h 48m
Trip: 9 days
Based on null reviews
Sat, Aug 29
PDX
Portland Airport
ORD
Chicago O'Hare Airport
9h 01m
Tue, Sep 8
ORD
Chicago O'Hare Airport
PDX
Portland Airport
9h 29m
Trip: 11 days
Based on null reviews
Wed, Aug 12
RDM
Bend/Redmond
ORD
Chicago O'Hare Airport
9h 28m
Wed, Aug 19
ORD
Chicago O'Hare Airport
RDM
Bend/Redmond
12h 09m
Trip: 8 days
Based on null reviews
Sat, Aug 29
PDX
Portland Airport
ORD
Chicago O'Hare Airport
9h 01m
Sat, Sep 5
ORD
Chicago O'Hare Airport
PDX
Portland Airport
17h 02m
Trip: 8 days
Based on null reviews
Sat, Aug 29
PDX
Portland Airport
ORD
Chicago O'Hare Airport
9h 01m
Sat, Sep 5
ORD
Chicago O'Hare Airport
PDX
Portland Airport
17h 07m
Trip: 8 days
Based on null reviews
Fri, Jul 31
PDX
Portland Airport
ORD
Chicago O'Hare Airport
11h 11m
Sun, Aug 2
ORD
Chicago O'Hare Airport
PDX
Portland Airport
11h 32m
Trip: 3 days
Based on null reviews
Thu, Aug 6
PDX
Portland Airport
ORD
Chicago O'Hare Airport
14h 42m
Sat, Aug 8
ORD
Chicago O'Hare Airport
PDX
Portland Airport
12h 52m
Trip: 3 days
Based on null reviews
Sat, Aug 8
PDX
Portland Airport
ORD
Chicago O'Hare Airport
8h 00m
Mon, Aug 10
ORD
Chicago O'Hare Airport
PDX
Portland Airport
9h 48m
Trip: 3 days
Based on null reviews
Fri, Jul 31
PDX
Portland Airport
ORD
Chicago O'Hare Airport
7h 00m
Sat, Aug 15
ORD
Chicago O'Hare Airport
PDX
Portland Airport
12h 52m
Trip: 16 days
Based on null reviews
Thu, Jul 30
PDX
Portland Airport
ORD
Chicago O'Hare Airport
34h 25m
Sat, Aug 1
ORD
Chicago O'Hare Airport
PDX
Portland Airport
28h 33m
Trip: 3 days
Based on null reviews
Mon, Aug 10
PDX
Portland Airport
ORD
Chicago O'Hare Airport
7h 41m
Sun, Aug 16
ORD
Chicago O'Hare Airport
PDX
Portland Airport
24h 19m
Trip: 7 days
Based on null reviews
Fri, Jul 31
PDX
Portland Airport
ORD
Chicago O'Hare Airport
31h 19m
Mon, Aug 3
ORD
Chicago O'Hare Airport
PDX
Portland Airport
15h 17m
Trip: 4 days
Based on null reviews
Thu, Jul 30
PDX
Portland Airport
ORD
Chicago O'Hare Airport
34h 25m
Sat, Aug 1
ORD
Chicago O'Hare Airport
PDX
Portland Airport
14h 59m
Trip: 3 days
Based on null reviews
Tue, Sep 15
PDX
Portland Airport
MDW
Chicago Midway Airport
8h 17m
Wed, Sep 23
MDW
Chicago Midway Airport
PDX
Portland Airport
7h 52m
Trip: 9 days
Based on null reviews
Sat, Aug 1
PDX
Portland Airport
ORD
Chicago O'Hare Airport
11h 11m
Mon, Aug 3
ORD
Chicago O'Hare Airport
PDX
Portland Airport
15h 17m
Trip: 3 days
Based on null reviews
Fri, Jul 31
PDX
Portland Airport
ORD
Chicago O'Hare Airport
7h 08m
Mon, Aug 3
ORD
Chicago O'Hare Airport
PDX
Portland Airport
11h 32m
Trip: 4 days
Based on null reviews
Sat, Oct 24
MFR
Medford
ORD
Chicago O'Hare Airport
22h 03m
Wed, Oct 28
ORD
Chicago O'Hare Airport
MFR
Medford
12h 44m
Trip: 5 days
Based on null reviews
Mon, Jul 27
PDX
Portland Airport
ORD
Chicago O'Hare Airport
11h 11m
Tue, Jul 28
ORD
Chicago O'Hare Airport
PDX
Portland Airport
11h 32m
Trip: 2 days
Based on null reviews
Fri, Jul 31
PDX
Portland Airport
ORD
Chicago O'Hare Airport
7h 08m
Mon, Aug 3
ORD
Chicago O'Hare Airport
PDX
Portland Airport
11h 32m
Trip: 4 days
Based on null reviews

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

Airports
Origin
Portland
$29
only
$29
Redmond
$121
only
$121
Eugene
$102
only
$102
Medford
$109
only
$109
Destination
Chicago
$29
only
$29
Sat, Aug 1
PDX
Portland Airport
ORD
Chicago O'Hare Airport
11h 11m
Based on null reviews
Sat, Aug 15
PDX
Portland Airport
ORD
Chicago O'Hare Airport
14h 30m
Based on null reviews
Thu, Aug 6
PDX
Portland Airport
ORD
Chicago O'Hare Airport
9h 01m
Based on null reviews
Thu, Aug 6
PDX
Portland Airport
ORD
Chicago O'Hare Airport
14h 42m
Based on null reviews
Sat, Aug 29
EUG
Eugene
ORD
Chicago O'Hare Airport
11h 02m
Based on null reviews
Wed, Jul 29
PDX
Portland Airport
ORD
Chicago O'Hare Airport
26h 45m
Based on null reviews
Mon, Aug 3
PDX
Portland Airport
ORD
Chicago O'Hare Airport
31h 19m
Based on null reviews
Mon, Aug 10
PDX
Portland Airport
ORD
Chicago O'Hare Airport
26h 51m
Based on null reviews
Sun, Aug 2
PDX
Portland Airport
ORD
Chicago O'Hare Airport
24h 50m
Based on null reviews
Mon, Aug 10
PDX
Portland Airport
ORD
Chicago O'Hare Airport
6h 48m
Based on null reviews
Tue, Aug 4
PDX
Portland Airport
ORD
Chicago O'Hare Airport
11h 11m
Based on null reviews
Fri, Jul 31
PDX
Portland Airport
ORD
Chicago O'Hare Airport
7h 00m
Based on null reviews
Sat, Aug 15
PDX
Portland Airport
ORD
Chicago O'Hare Airport
8h 00m
Based on null reviews
Mon, Aug 3
PDX
Portland Airport
ORD
Chicago O'Hare Airport
126h 48m
Based on null reviews
Mon, Aug 17
MFR
Medford
ORD
Chicago O'Hare Airport
12h 09m
Based on null reviews
Sun, Aug 2
PDX
Portland Airport
ORD
Chicago O'Hare Airport
33h 05m
Based on null reviews
Sat, Aug 8
PDX
Portland Airport
ORD
Chicago O'Hare Airport
8h 00m
Based on null reviews
Sat, Aug 1
EUG
Eugene
ORD
Chicago O'Hare Airport
7h 03m
Based on null reviews
Fri, Jul 31
PDX
Portland Airport
ORD
Chicago O'Hare Airport
21h 11m
Based on null reviews
Tue, Sep 8
RDM
Bend/Redmond
ORD
Chicago O'Hare Airport
7h 45m
Based on null reviews
*
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 and someone from our team will get back to you promptly.

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