PDX - MDW

$109 Find Cheap Flights from Portland 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 from Portland to Midway departing on 2/4. 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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago, 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 Portland to Chicago, 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
$236
Overall average: $197
Southwest
Wed 1/21Sat 1/24
PDX - MDW • 1 stop
Cheapest non-stop
$237
Typical prices: $197-$567
Southwest
Thu 1/8Mon 1/12
PDX - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
PDX's easy navigation simplifies check-in and security.
Use the CTA Orange Line for a quick ride from MDW.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $237 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
January
Cheapest • 45% price drop
May
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 Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Portland to Midway (PDX-MDW)

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

Wed, Jan 21 - Sat, Jan 24
Southwest Logo
2:15 pm - 10:50 pm
PDX
-
MDW
6h 35m1 stop
Southwest Logo
1:10 pm - 8:40 pm
MDW
-
PDX
9h 30m1 stop
$236Southwest
Fri, Jan 9 - Wed, Jan 14
Southwest Logo
11:05 am - 9:50 pm
PDX
-
MDW
8h 45m1 stop
Southwest Logo
3:35 pm - 6:00 pm
MDW
-
PDX
4h 25mnonstop
$237Southwest
Sat, Jan 24 - Mon, Jan 26
Southwest Logo
6:00 am - 11:55 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
8:10 am - 3:40 pm
MDW
-
PDX
9h 30m2 stops
$242Southwest
Sat, Jan 24 - Sun, Jan 25
Southwest Logo
6:00 am - 11:55 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
8:10 am - 10:45 am
MDW
-
PDX
4h 35mnonstop
$243Southwest
Fri, Jan 9 - Wed, Jan 14
Southwest Logo
11:30 am - 10:50 pm
PDX
-
MDW
9h 20m1 stop
Southwest Logo
5:05 am - 10:50 am
MDW
-
PDX
7h 45m1 stop
$246Southwest
Thu, Jan 8 - Tue, Jan 13
Southwest Logo
2:15 pm - 9:50 pm
PDX
-
MDW
5h 35m1 stop
Southwest Logo
3:35 pm - 6:00 pm
MDW
-
PDX
4h 25mnonstop
$247Southwest
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:30 am - 12:25 pm
PDX
-
MDW
3h 55mnonstop
Southwest Logo
8:10 am - 3:40 pm
MDW
-
PDX
9h 30m2 stops
$252Southwest
Sat, Jan 24 - Sun, Jan 25
Southwest Logo
8:45 am - 4:25 pm
PDX
-
MDW
5h 40m1 stop
Southwest Logo
8:10 am - 10:45 am
MDW
-
PDX
4h 35mnonstop
$253Southwest
Thu, Jan 8 - Thu, Jan 15
Frontier Logo
12:05 pm - 2:05 pm
PDX
-
MDW
24h 00m1 stop
Frontier Logo
11:05 am - 10:33 am
MDW
-
PDX
25h 28m2 stops
$255Frontier
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
9:55 am - 7:45 pm
PDX
-
MDW
7h 50m1 stop
Southwest Logo
2:35 pm - 7:55 pm
MDW
-
PDX
7h 20m1 stop
$256Southwest
Booking Insights

KAYAK's insights & trends for Portland to Midway flights

Get data-powered insights and trends into flights from Portland to Midway 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 Portland to Chicago Midway Airport?

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Chicago Midway Airport, 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 Portland to Chicago Midway Airport is January, where tickets cost $197 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $592 and $494 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $309 on average.

Expert advice

Expert advice for your flight from Portland to Midway

 
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.
Airports
PDX

PDX offers easy navigation with a single main terminal and clear signage, making check-in and security a breeze.

MDW

Take the CTA Orange Line from MDW to downtown Chicago for a quick, traffic-free 25-30 minute ride.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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 Leigh

Gabriel Leigh

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 seasonNovember
Cheapest flight$109
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from Portland to Chicago Midway Airport

When to book flights from Portland to Midway

Are your dates flexible? Find out the best times to travel from Portland to Midway 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 Portland to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Portland to Chicago Midway Airport was $109 for a one-way ticket and $236 for a round-trip.

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

    No

  • Which airports will I be using when flying from Portland to Chicago Midway Airport?

    When flying out of Portland you will be using Portland. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

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

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

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

    The Boeing 737 MAX 9 is the aircraft model that flies most regularly on the Portland to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Portland to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Portland and Chicago Midway Airport.

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

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

  • Which is the best airline for flights from Portland to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Southwest and Delta. With an average price for the route of $382 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $377 and an overall rating of 7.9.

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland 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 Portland 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 Portland 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 Portland with another airline. Booking your flights between Portland and MDW 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 Portland 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 Portland 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 Portland to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $166 or less one-way and $316 or less round-trip.

Prefer to fly direct from Portland to Chicago Midway Airport?

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

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from Portland to Midway

 
See real verified KAYAK customer reviews for airlines flying from Portland to Chicago. 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 Portland to Midway? 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.
7.9
SouthwestOverall score based on 4251 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

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

Information on your arrival and departure airports