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$50 Find cheap flights from Oregon to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 6/30
Sun 7/7

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In the last 7 days travelers have searched 42,787,818 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

June

Cheapest flight

$50
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Portland to Chicago O'Hare Airport

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.

See more FAQs

Prefer to fly non-stop from Oregon to Chicago?

Find which airlines fly direct from Oregon to Chicago, which days they fly and book direct flights.

Nonstop departures

Oregon to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights

Nonstop returns

Chicago to Oregon

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights
See more direct flights

Book cheap flights from Oregon to Chicago

Recent round-trip flight deals

8/21Wed
nonstopSpirit Airlines
3h 50mPDX-ORD
8/28Wed
nonstopSpirit Airlines
4h 30mORD-PDX
$86
9/7Sat
nonstopSpirit Airlines
3h 50mPDX-ORD
9/11Wed
nonstopSpirit Airlines
4h 30mORD-PDX
$87
8/24Sat
1 stop
10h 17mPDX-ORD
8/28Wed
nonstop
4h 30mORD-PDX
$135
9/18Wed
nonstop
3h 50mPDX-ORD
9/23Mon
1 stop
6h 52mORD-PDX
$147
6/10Mon
2 stopsFrontier
11h 51mPDX-ORD
6/12Wed
1 stopFrontier
11h 57mORD-PDX
$168
9/4Wed
1 stopFrontier
9h 04mPDX-MDW
9/17Tue
1 stopFrontier
19h 40mMDW-PDX
$176
8/27Tue
nonstopAlaska Airlines
4h 03mPDX-ORD
9/3Tue
nonstopAlaska Airlines
4h 30mORD-PDX
$179
9/3Tue
1 stopAlaska Airlines
7h 15mPDX-ORD
9/14Sat
nonstopAlaska Airlines
4h 30mORD-PDX
$188
7/15Mon
1 stopAmerican Airlines
8h 14mBOI-ORD
7/20Sat
1 stopAmerican Airlines
7h 36mORD-BOI
$192
8/14Wed
1 stopAmerican Airlines
8h 24mEUG-ORD
8/20Tue
1 stopAmerican Airlines
7h 59mORD-EUG
$232

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/21Wed
nonstopSpirit Airlines
3h 50mPDX-ORD
$50
6/8Sat
nonstopSpirit Airlines
4h 07mPDX-ORD
$53
7/4Thu
nonstopAlaska Airlines
4h 04mPDX-ORD
$90
6/8Sat
1 stopFrontier
8h 13mPDX-MDW
$90
6/10Mon
2 stopsFrontier
11h 51mPDX-ORD
$95
6/11Tue
2 stops
24h 52mPDX-RFD
$97
7/8Mon
1 stopSun Country Air
16h 00mPDX-ORD
$103
7/21Sun
1 stopSun Country Air
16h 20mPDX-ORD
$110
6/11Tue
3 stops
27h 11mPDX-RFD
$111
10/17Thu
1 stopAlaska Airlines
8h 11mPDX-ORD
$118

Search by stops

Search by airline

Search by price

Last minute flights from Oregon to Chicago

Last minute flight, train and bus deals

6/5Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
6/8Sat
nonstopSpirit Airlines
4h 27mORD-PDX
$99
6/5Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
6/22Sat
nonstopSpirit Airlines
4h 27mORD-PDX
$101
6/5Wed
nonstop
4h 07mPDX-ORD
6/8Sat
multi-stop
12h 34mORD-PDX
$135
6/1Sat
multi-stop
20h 02mPDX-ORD
6/8Sat
nonstop
4h 27mORD-PDX
$153
6/2Sun
multi-stopFrontier
10h 23mPDX-ORD
6/5Wed
multi-stopFrontier
11h 57mORD-PDX
$180
6/1Sat
multi-stopFrontier
8h 36mPDX-MDW
6/9Sun
multi-stopFrontier
13h 27mMDW-PDX
$180
6/4Tue
nonstopAlaska Airlines
4h 05mPDX-ORD
6/6Thu
nonstopAlaska Airlines
4h 20mORD-PDX
$308
6/4Tue
nonstopAlaska Airlines
4h 05mPDX-ORD
6/5Wed
nonstopAlaska Airlines
4h 20mORD-PDX
$327
6/3Mon
multi-stopAmerican Airlines
6h 10mBOI-ORD
6/7Fri
multi-stopAmerican Airlines
7h 00mORD-BOI
$352
6/2Sun
multi-stopAmerican Airlines
8h 00mRDM-ORD
6/7Fri
multi-stopAmerican Airlines
6h 51mORD-RDM
$845

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Oregon

Cabin classes:

$412
$954
$615
$142