MDW - PDX

$118 Find Cheap Flights from Chicago Midway Airport to Portland

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 Portland 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 Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, 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 Portland, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$207
Overall average: $346
Southwest
Tue 4/28Wed 5/6
MDW - PDX • Non-stop
Cheapest one-way
$118
Overall average: $174
Frontier
Tue 4/14
MDW - PDX • 2 stops
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal offers easy navigation.
Use Trimet Red Line from PDX for downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $207 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 4h 22m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Denver (DEN)
Cheapest • Avg $243 (round-trip)
Denver (DEN)
Shortest trip • 6h 41m (one-way)
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 21% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Portland!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Portland (MDW-PDX)

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

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
Sat, Apr 25 - Tue, May 5
Southwest Logo
10:15 am - 6:45 pm
MDW
-
PDX
10h 30m
2 stops
Southwest Logo
7:00 am - 7:35 pm
PDX
-
MDW
10h 35m
2 stops
$237Southwest
Wed, Apr 15 - Tue, Apr 28
Southwest Logo
8:50 pm - 11:10 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$239Southwest
Booking Insights

KAYAK's insights & trends for Midway to Portland flights

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

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

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

Your flight ticket price will generally be cheaper if you fly to Portland 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.

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

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 Portland, 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 Portland is March, where tickets cost $308 (return) on average. On the other hand, the most expensive months are June and October, where the average cost of round-trip tickets is $543 and $538 respectively.

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

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.

Find deals
Expert advice

Expert advice for your flight from Midway to Portland

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on PDX

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more

Good to know

Low seasonJanuary
Cheapest flight$118
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 38% increase in price.
Flight from Chicago Midway Airport to Portland

When to book flights from Midway to Portland

Are your dates flexible? Find out the best times to travel from Midway to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Portland flights

  • What is the cheapest flight from Chicago Midway Airport to Portland?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Portland was $118 for a one-way ticket and $207 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Portland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Portland?

    American Airlines, Alaska Airlines, Hawaiian Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago Midway Airport to Portland flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Portland?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Portland flight route.

  • On which days can I fly direct from Chicago Midway Airport to Portland?

    There are nonstop flights from Chicago Midway Airport to Portland on a daily basis.

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

    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 Portland.

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

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

    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 Portland with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PDX can sometimes prove cheaper using this method.

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

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

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $133 or less one-way and $248 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Portland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Portland.
Find which airlines fly direct from Chicago Midway Airport to Portland Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Portland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Portland to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. 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 Portland? 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
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
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 Portland

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Portland (PDX)