MDW

$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 2/27. 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
1 adult, Economy, 0 bags

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

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Everything you should know

Cheapest round-trip
$217
Overall average: $253
Delta
Tue 2/24Wed 3/4
PDX - MDW • 1 stop
Cheapest non-stop
$217
Typical prices: $329-$637
Southwest
Thu 3/12Mon 3/16
PDX - MDW • Non-stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Oregon to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oregon to Midway 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.

Recent round-trip flight deals from Oregon to Midway

Tue, Feb 24 - Wed, Mar 4
Delta Logo
12:40 am - 9:06 am
PDX
-
MDW
6h 26m
1 stop
Delta Logo
1:49 pm - 8:30 pm
MDW
-
PDX
8h 41m
1 stop
$217Delta
Tue, May 5 - Wed, Jun 10
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
5:30 pm - 7:50 pm
MDW
-
PDX
4h 20mnonstop
$221Southwest
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
5:05 am - 6:45 pm
PDX
-
MDW
11h 40m
2 stops
Southwest Logo
3:35 pm - 6:00 pm
MDW
-
PDX
4h 25mnonstop
$222Southwest
Fri, Feb 20 - Mon, Feb 23
Delta Logo
12:40 am - 11:03 am
PDX
-
MDW
8h 23m
1 stop
Delta Logo
1:49 pm - 8:30 pm
MDW
-
PDX
8h 41m
1 stop
$227Delta
Sat, Mar 14 - Tue, Mar 17
Southwest Logo
11:55 pm - 5:45 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
8:45 pm - 11:10 pm
MDW
-
PDX
4h 25mnonstop
$231Southwest
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
5:05 am - 6:45 pm
PDX
-
MDW
11h 40m
2 stops
Southwest Logo
8:25 am - 1:35 pm
MDW
-
PDX
7h 10m
1 stop
$232Southwest
Sat, Feb 14 - Tue, Feb 17
Delta Logo
6:00 am - 4:14 pm
PDX
-
MDW
8h 14m
1 stop
Delta Logo
1:49 pm - 8:30 pm
MDW
-
PDX
8h 41m
1 stop
$234Delta
Sat, Feb 14 - Tue, Feb 17
Southwest Logo
7:15 am - 1:15 pm
PDX
-
MDW
4h 00mnonstop
Southwest Logo
8:10 am - 10:45 am
MDW
-
PDX
4h 35mnonstop
$236Southwest
Thu, Feb 19 - Mon, Feb 23
Delta Logo
12:40 am - 9:06 am
PDX
-
MDW
6h 26m
1 stop
Delta Logo
1:49 pm - 8:30 pm
MDW
-
PDX
8h 41m
1 stop
$237Delta
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
10:00 am - 6:10 pm
PDX
-
MDW
6h 10m
1 stop
Southwest Logo
10:30 pm - 12:55 am
MDW
-
PDX
4h 25mnonstop
$241Southwest
Useful Info

Good to know

Low seasonDecember
Cheapest flight$90
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from Boise 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.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)