$118 Find Cheap Flights from Chicago Midway Airport to Oregon

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 4/14. 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 Oregon

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$207
Eugene
Eugene1 stop$237
Redmond
Redmond2 stops$370
Medford
Medford2 stops$321
Boise
Boise1 stop$294
Portland
Portlandnonstop$207
Eugene
Eugene1 stop$237
Redmond
Redmond2 stops$370
Medford
Medford2 stops$321
Boise
Boise1 stop$294

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

Tue, Apr 28 - Wed, May 6
Southwest Logo
8:50 pm - 11:10 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$207Southwest
Tue, Apr 28 - Wed, May 6
Southwest Logo
3:40 pm - 8:45 pm
MDW
-
PDX
7h 05m
1 stop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$213Southwest
Sat, Apr 25 - Tue, May 5
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
5:40 am - 11:35 am
PDX
-
MDW
3h 55mnonstop
$215Southwest
Sat, Apr 25 - Sat, May 2
Southwest Logo
5:10 am - 12:55 pm
MDW
-
PDX
9h 45m
1 stop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$217Southwest
Sat, Apr 25 - Sat, May 2
Southwest Logo
10:15 am - 6:45 pm
MDW
-
PDX
10h 30m
2 stops
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$222Southwest
Tue, Apr 28 - Tue, May 5
Delta Logo
2:12 pm - 8:07 pm
MDW
-
PDX
7h 55m
1 stop
Delta Logo
12:30 am - 8:46 am
PDX
-
MDW
6h 16m
1 stop
$227Delta
Sat, Apr 25 - Tue, May 5
Southwest Logo
1:55 pm - 6:45 pm
MDW
-
PDX
6h 50m
1 stop
Southwest Logo
7:00 am - 7:35 pm
PDX
-
MDW
10h 35m
2 stops
$232Southwest
Thu, Apr 16 - Sun, Apr 19
Multiple Airlines Logo
4:15 pm - 11:03 am
MDW
-
PDX
20h 48m
2 stops
Multiple Airlines Logo
7:46 pm - 3:04 pm
PDX
-
MDW
17h 18m
1 stop
$234Multiple Airlines
Wed, May 13 - Tue, May 19
Delta Logo
1:59 pm - 11:42 pm
MDW
-
MFR
11h 43m
2 stops
Delta Logo
5:15 am - 5:56 pm
MFR
-
MDW
10h 41m
2 stops
$321Delta
Sun, May 10 - Tue, May 19
Delta Logo
9:22 am - 11:55 pm
MDW
-
MFR
16h 33m
2 stops
Delta Logo
5:15 am - 5:56 pm
MFR
-
MDW
10h 41m
2 stops
$351Delta
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 72 hours was to Portland, at $217 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 72 hours was $217.

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 at night, when round-trip flights cost $317 on average. Morning departures are around 7% cheaper than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the evening, which is peak travel time and where the average cost of a ticket is $354.

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 $279, 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 $308 (return) on average. On the other hand, the most expensive months are June and October, when the average cost of round-trip tickets is $543 and $538 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 Monday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Thursday, and avoid Sundays for better deals.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$118
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago Midway Airport to Portland

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 4318 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)