$157 Find Cheap Flights from Chicago Midway Airport to Oregon - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Oregon departing on 8/24. 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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Cheap Flights from Midway to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$357
Eugene
Eugene1 stop$334
Redmond
Redmond2 stops$458
Medford
Medford2 stops$417
Boise
Boisenonstop$313
Portland
Portlandnonstop$357
Eugene
Eugene1 stop$334
Redmond
Redmond2 stops$458
Medford
Medford2 stops$417
Boise
Boisenonstop$313

Book Cheap Midway to Oregon Plane Tickets

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

Mon, Aug 17 - Thu, Aug 20
Southwest Logo
11:40 am - 2:10 pm
MDW
-
BOI
3h 30mnonstop
Southwest Logo
12:10 pm - 4:30 pm
BOI
-
MDW
3h 20mnonstop
$313Southwest
Mon, Aug 17 - Mon, Aug 24
Southwest Logo
11:40 am - 2:10 pm
MDW
-
BOI
3h 30mnonstop
Southwest Logo
12:10 pm - 4:30 pm
BOI
-
MDW
3h 20mnonstop
$313Southwest
Tue, Aug 18 - Thu, Aug 20
Southwest Logo
6:00 pm - 11:10 pm
MDW
-
BOI
6h 10m
1 stop
Southwest Logo
12:10 pm - 4:30 pm
BOI
-
MDW
3h 20mnonstop
$323Southwest
Mon, Aug 17 - Thu, Aug 20
Southwest Logo
4:55 pm - 11:55 pm
MDW
-
BOI
8h 00m
1 stop
Southwest Logo
12:10 pm - 4:30 pm
BOI
-
MDW
3h 20mnonstop
$323Southwest
Mon, Aug 17 - Mon, Aug 24
Southwest Logo
11:40 am - 2:10 pm
MDW
-
BOI
3h 30mnonstop
Southwest Logo
3:45 pm - 11:45 pm
BOI
-
MDW
7h 00m
1 stop
$323Southwest
Mon, Aug 17 - Mon, Aug 24
Southwest Logo
11:40 am - 2:10 pm
MDW
-
BOI
3h 30mnonstop
Southwest Logo
6:00 am - 5:00 pm
BOI
-
MDW
10h 00m
2 stops
$328Southwest
Tue, Aug 18 - Thu, Aug 20
Southwest Logo
3:10 pm - 11:10 pm
MDW
-
BOI
9h 00m
2 stops
Southwest Logo
12:10 pm - 4:30 pm
BOI
-
MDW
3h 20mnonstop
$328Southwest
Mon, Aug 17 - Thu, Aug 20
Southwest Logo
11:40 am - 2:10 pm
MDW
-
BOI
3h 30mnonstop
Southwest Logo
6:00 am - 5:00 pm
BOI
-
MDW
10h 00m
2 stops
$328Southwest
Tue, Oct 6 - Tue, Oct 13
Delta Logo
5:31 pm - 11:59 pm
MDW
-
BOI
7h 28m
1 stop
Delta Logo
5:30 am - 11:47 am
BOI
-
MDW
5h 17m
1 stop
$333Delta
Tue, Oct 6 - Sat, Oct 10
Delta Logo
5:31 pm - 11:59 pm
MDW
-
BOI
7h 28m
1 stop
Delta Logo
1:40 pm - 10:33 pm
BOI
-
MDW
7h 53m
1 stop
$333Delta
Booking Insights

KAYAK's insights & trends for Midway to Oregon flights

Get data-powered insights and trends into flights from Midway to Oregon to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Oregon flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Oregon from Chicago Midway Airport found in the last 5 days was to Portland, at $307 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Portland (PDX), and the cheapest round-trip airline ticket found on this route in the last 5 days was $307.

What is the cheapest time of day to fly to Oregon?

The average price for all round-trip flights from Chicago Midway Airport to Oregon depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Oregon is generally in the evening, when round-trip flights cost $316 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $573.

Can I save money by flying with a layover from Chicago Midway Airport to Oregon?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $407, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Oregon?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Oregon, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Oregon is March, when tickets cost $227 (return) on average. On the other hand, the most expensive months are October and July, when the average cost of round-trip tickets is $538 and $427 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Oregon?

The average price of all round-trip flights from Chicago Midway Airport to Oregon clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Oregon on a Saturday and more expensive on a Tuesday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

Find deals

Good to know

Low season

February

Cheapest flight

$157
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago Midway Airport to Boise

FAQs - booking Oregon flights

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

    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 Chicago Midway Airport to Oregon.

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

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

    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 from Chicago Midway Airport to Oregon with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Oregon?

    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 from Chicago Midway Airport to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oregon. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Oregon? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4227 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Long layover in Chicago. Wish that could have been lessened.

Everything you need to know for your flight from Midway to Oregon

Information on your arrival and departure airports

Chicago Midway Airport (MDW)