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$90 Find cheap flights from Oregon to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 6/4. 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
Thu 6/27
Thu 7/4

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

June

Cheapest flight

$90
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Portland to Chicago Midway Airport

FAQs for booking Oregon to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Oregon to Chicago Midway Airport?

    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 Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oregon to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?

    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 Midway Airport 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 Midway Airport?

    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 Midway Airport 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 Midway Airport?

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

Nonstop departures

Oregon to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights

Nonstop returns

Chicago Midway to Oregon

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights
See more direct flights

Book cheap flights from Oregon to Chicago

Recent round-trip flight deals

9/10Tue
1 stopFrontier
9h 04mPDX-MDW
9/18Wed
1 stopFrontier
19h 54mMDW-PDX
$178
8/21Wed
1 stopFrontier
9h 04mPDX-MDW
8/28Wed
1 stopFrontier
11h 04mMDW-PDX
$179
6/10Mon
1 stopFrontier
10h 20mPDX-MDW
6/15Sat
1 stopFrontier
12h 11mMDW-PDX
$180
9/13Fri
1 stopFrontier
9h 04mPDX-MDW
9/17Tue
1 stopFrontier
19h 54mMDW-PDX
$181
6/10Mon
1 stopFrontier
10h 20mPDX-MDW
6/13Thu
1 stopFrontier
12h 00mMDW-PDX
$182
6/8Sat
1 stopFrontier
24h 33mPDX-MDW
6/11Tue
1 stopFrontier
26h 50mMDW-PDX
$183
6/8Sat
2 stopsFrontier
8h 56mPDX-MDW
6/11Tue
1 stopFrontier
11h 50mMDW-PDX
$185
6/10Mon
2 stopsFrontier
11h 55mPDX-MDW
6/12Wed
1 stopFrontier
9h 32mMDW-PDX
$187
8/6Tue
1 stopDelta
7h 03mBOI-MDW
8/12Mon
1 stopDelta
5h 50mMDW-BOI
$257
7/11Thu
2 stopsDelta
11h 39mBOI-MDW
7/16Tue
2 stopsDelta
11h 51mMDW-BOI
$278

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Recent one-way flight deals

6/4Tue
1 stopFrontier
7h 05mPDX-MDW
$90
6/2Sun
1 stopFrontier
28h 56mPDX-MDW
$95
6/3Mon
1 stopFrontier
11h 14mPDX-MDW
$96
6/2Sun
2 stopsFrontier
31h 30mPDX-MDW
$99
6/8Sat
1 stopFrontier
24h 33mPDX-MDW
$101
9/5Thu
1 stopDelta
6h 03mPDX-MDW
$108
9/11Wed
1 stopDelta
5h 51mPDX-MDW
$169
6/30Sun
2 stops
18h 19mPDX-MDW
$234
8/1Thu
2 stopsAllegiant Air
17h 47mEUG-MDW
$239
6/30Sun
3 stops
26h 38mPDX-MDW
$263

Search by stops

Search by airline

Search by price

Last minute flights from Oregon to Midway

Last minute flight, train and bus deals

6/2Sun
multi-stopFrontier
8h 21mPDX-MDW
6/10Mon
multi-stopFrontier
20h 01mMDW-PDX
$182
5/29Wed
multi-stopFrontier
8h 36mPDX-MDW
6/3Mon
multi-stopFrontier
17h 15mMDW-PDX
$183
6/2Sun
multi-stopFrontier
8h 21mPDX-MDW
6/10Mon
multi-stopFrontier
21h 40mMDW-PDX
$187
6/2Sun
multi-stopFrontier
8h 21mPDX-MDW
6/6Thu
multi-stopFrontier
11h 51mMDW-PDX
$188
5/30Thu
multi-stopFrontier
28h 56mPDX-MDW
6/3Mon
multi-stopFrontier
20h 34mMDW-PDX
$189
5/29Wed
multi-stopFrontier
31h 30mPDX-MDW
6/1Sat
multi-stopFrontier
27h 57mMDW-PDX
$193
5/31Fri
multi-stopFrontier
18h 18mPDX-MDW
6/8Sat
multi-stopFrontier
12h 19mMDW-PDX
$261
5/31Fri
multi-stopFrontier
18h 18mPDX-MDW
6/3Mon
multi-stopFrontier
17h 15mMDW-PDX
$265
5/29Wed
multi-stopDelta
7h 50mPDX-MDW
6/1Sat
multi-stopDelta
8h 23mMDW-PDX
$352
5/29Wed
multi-stopDelta
7h 50mPDX-MDW
5/31Fri
multi-stopDelta
6h 15mMDW-PDX
$377

Search by stops

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Oregon

Cabin classes:

$737