MDW

$144 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 6/7. 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

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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

Sun, May 24 - Sat, May 30
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
$305Southwest
Thu, May 28 - Wed, Jun 3
Southwest Logo
5:10 am - 11:05 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
5:35 pm - 11:00 pm
MDW
-
PDX
7h 25m
1 stop
$315Southwest
Sat, Jun 27 - Sun, Jul 5
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
9:45 pm - 12:05 am
MDW
-
PDX
4h 20mnonstop
$316Southwest
Sat, Jul 11 - Wed, Jul 15
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
3:05 pm - 10:10 pm
MDW
-
PDX
9h 05m
2 stops
$320Southwest
Sun, May 24 - Sat, May 30
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
1:55 pm - 10:05 pm
MDW
-
PDX
10h 10m
1 stop
$321Southwest
Wed, Jul 22 - Thu, Jul 30
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
5:00 am - 9:55 am
MDW
-
PDX
6h 55m
1 stop
$322Southwest
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
2:44 pm - 10:02 pm
PDX
-
MDW
29h 18m
2 stops
Multiple Airlines Logo
8:03 pm - 2:19 pm
MDW
-
PDX
20h 16m
1 stop
$328Multiple Airlines
Tue, Jun 23 - Tue, Jun 30
Delta Logo
5:30 am - 1:09 pm
BOI
-
MDW
6h 39m
1 stop
Delta Logo
1:49 pm - 8:55 pm
MDW
-
BOI
8h 06m
1 stop
$335Delta
Wed, Jul 8 - Tue, Jul 14
Delta Logo
10:29 am - 6:18 pm
BOI
-
MDW
6h 49m
1 stop
Delta Logo
1:49 pm - 12:05 am
MDW
-
BOI
11h 16m
2 stops
$340Delta
Wed, Aug 12 - Wed, Aug 19
Delta Logo
11:35 am - 9:46 pm
BOI
-
MDW
9h 11m
2 stops
Delta Logo
6:00 am - 2:34 pm
MDW
-
BOI
9h 34m
2 stops
$345Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$144
Best time to beat the crowds with an average 3% drop 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.

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
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)