MDW

$71 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 12/7. 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

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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$237
Typical prices: $361-$623
Delta
Mon 3/9Wed 3/11
PDX - MDW • 1 stop
Cheapest non-stop
$247
Typical prices: $281-$643
Southwest
Wed 12/10Sun 12/14
PDX - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Mon, Mar 9 - Wed, Mar 11
Delta Logo
12:55 am - 8:54 amPDX-MDW
5h 59m1 stop
Delta Logo
9:20 am - 4:51 pmMDW-PDX
9h 31m1 stop
$237Delta
Find Deal
Sat, Dec 6 - Sat, Dec 13
Delta Logo
11:20 pm - 8:54 amPDX-MDW
7h 34m1 stop
Delta Logo
1:50 pm - 8:52 pmMDW-PDX
9h 02m1 stop
$238Delta
Find Deal
Thu, Dec 4 - Tue, Dec 9
Delta Logo
12:32 am - 9:19 amPDX-MDW
6h 47m1 stop
Delta Logo
1:50 pm - 8:52 pmMDW-PDX
9h 02m1 stop
$247Delta
Find Deal
Thu, Feb 19 - Sun, Feb 22
Southwest Logo
2:25 pm - 10:25 pmPDX-MDW
6h 00m1 stop
Southwest Logo
5:20 am - 10:55 amMDW-PDX
7h 35m1 stop
$256Southwest
Find Deal
Fri, Dec 5 - Mon, Dec 8
Delta Logo
11:54 am - 11:47 pmPDX-MDW
9h 53m1 stop
Delta Logo
10:49 am - 7:35 pmMDW-PDX
10h 46m1 stop
$257Delta
Find Deal
Wed, Dec 10 - Sun, Dec 14
Southwest Logo
6:15 am - 12:10 pmPDX-MDW
3h 55mnonstop
Southwest Logo
7:50 am - 6:30 pmMDW-PDX
12h 40m1 stop
$262Southwest
Find Deal
Sun, Nov 23 - Thu, Nov 27
Frontier Logo
3:59 pm - 2:31 pmPDX-MDW
20h 32m1 stop
Frontier Logo
4:00 pm - 8:04 amMDW-PDX
18h 04m2 stops
$295Frontier
Find Deal
Sun, Dec 21 - Wed, Dec 31
Frontier Logo
12:47 pm - 9:50 pmPDX-MDW
7h 03m1 stop
Frontier Logo
6:12 am - 11:37 amMDW-PDX
31h 25m2 stops
$301Frontier
Find Deal
Sun, Dec 21 - Thu, Dec 25
Multiple Airlines Logo
12:38 pm - 9:50 pmBOI-MDW
8h 12m1 stop
Multiple Airlines Logo
6:12 am - 3:04 pmMDW-BOI
33h 52m2 stops
$358Multiple Airlines
Find Deal
Mon, Dec 22 - Sun, Jan 4
Multiple Airlines Logo
5:55 pm - 10:19 amEUG-MDW
14h 24m1 stop
Multiple Airlines Logo
3:01 pm - 1:48 pmMDW-EUG
24h 47m1 stop
$409Multiple Airlines
Find Deal
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$71
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.