PWM - MDW

$100 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 10/31. 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

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
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Flights Deals

Cheap Flights from Portland to Midway (PWM-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

Sat, Aug 30 - Sun, Aug 31
Southwest Logo
1:15 pm - 6:35 pmPWM-MDW
6h 20m1 stop
Southwest Logo
5:55 pm - 9:15 pmMDW-PWM
2h 20mnonstop
$209Southwest
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Thu, Aug 28 - Tue, Sep 2
Southwest Logo
10:35 am - 12:05 pmPWM-MDW
2h 30mnonstop
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
$217Southwest
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Sat, Aug 30 - Sun, Aug 31
Southwest Logo
5:45 am - 1:30 pmPWM-MDW
8h 45m2 stops
Southwest Logo
5:55 pm - 9:15 pmMDW-PWM
2h 20mnonstop
$223Southwest
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Thu, Aug 28 - Tue, Sep 2
Southwest Logo
5:40 pm - 10:00 pmPWM-MDW
5h 20m1 stop
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
$227Southwest
Find Deal
Thu, Aug 28 - Thu, Sep 4
Southwest Logo
5:40 pm - 10:00 pmPWM-MDW
5h 20m1 stop
Southwest Logo
5:40 am - 1:15 pmMDW-PWM
6h 35m1 stop
$237Southwest
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Thu, Sep 11 - Sun, Sep 14
Southwest Logo
10:35 am - 12:05 pmPWM-MDW
2h 30mnonstop
Southwest Logo
7:10 pm - 10:25 pmMDW-PWM
2h 15mnonstop
$238Southwest
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Tue, Sep 16 - Sat, Sep 20
Delta Logo
6:00 am - 11:48 amPWM-MDW
6h 48m1 stop
Delta Logo
9:35 am - 10:00 pmMDW-PWM
11h 25m2 stops
$242Delta
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Tue, Sep 16 - Sat, Sep 20
Delta Logo
1:40 pm - 9:36 pmPWM-MDW
8h 56m2 stops
Delta Logo
1:08 pm - 10:00 pmMDW-PWM
7h 52m2 stops
$247Delta
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Wed, Aug 20 - Sun, Aug 24
Southwest Logo
5:50 am - 11:45 amPWM-MDW
6h 55m1 stop
Southwest Logo
7:10 pm - 10:25 pmMDW-PWM
2h 15mnonstop
$248Southwest
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Wed, Nov 5 - Sat, Nov 8
Delta Logo
6:30 am - 4:14 pmPWM-MDW
10h 44m2 stops
Delta Logo
6:00 am - 12:31 pmMDW-PWM
5h 31m1 stop
$249Delta
Find Deal
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.

For Portland to Chicago Midway Airport, Thursday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago Midway Airport back to Portland, the best deals are generally found on Tuesday, with Monday being the most expensive.

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.

No, with an average price for the route of $397, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$100
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 $100 for a one-way ticket and $209 for a round-trip.

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

    No, a passport isn't needed to fly from Portland to Chicago Midway Airport. However, local authorities might ask for an official ID.

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

    American Airlines, and Delta 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 Embraer 175 is the aircraft model that flies most regularly on the Portland to Chicago Midway Airport flight route.

  • 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 $390 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $327 and an overall rating of 8.0.

  • 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 $147 or less one-way and $321 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.
8.0
SouthwestOverall score based on 4246 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

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