MDW - PWM

$100 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 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 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
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Cheap Flights from Midway to Portland (MDW-PWM)

 
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

Sat, Sep 6 - Tue, Sep 9
Southwest Logo
12:50 pm - 4:05 pmMDW-PWM
2h 15mnonstop
Southwest Logo
10:30 am - 12:00 pmPWM-MDW
2h 30mnonstop
$217Southwest
Find Deal
Tue, Sep 9 - Sat, Sep 13
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
Southwest Logo
2:55 pm - 8:45 pmPWM-MDW
6h 50m1 stop
$227Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
4:25 pm - 12:03 amMDW-PWM
6h 38m1 stop
Delta Logo
11:48 am - 5:37 pmPWM-MDW
6h 49m1 stop
$228Delta
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Tue, Sep 9 - Sat, Sep 13
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
Southwest Logo
5:45 am - 1:30 pmPWM-MDW
8h 45m2 stops
$232Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
1:08 pm - 12:03 amMDW-PWM
9h 55m2 stops
Delta Logo
11:48 am - 5:37 pmPWM-MDW
6h 49m1 stop
$233Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
4:25 pm - 12:03 amMDW-PWM
6h 38m1 stop
Delta Logo
11:48 am - 5:37 pmPWM-MDW
6h 49m1 stop
$237Delta
Find Deal
Wed, Sep 3 - Tue, Sep 9
Delta Logo
4:25 pm - 12:03 amMDW-PWM
6h 38m1 stop
Delta Logo
11:50 am - 9:26 pmPWM-MDW
10h 36m2 stops
$242Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
4:25 pm - 12:03 amMDW-PWM
6h 38m1 stop
Delta Logo
11:48 am - 5:37 pmPWM-MDW
6h 49m1 stop
$244Delta
Find Deal
Wed, Sep 3 - Tue, Sep 9
Delta Logo
1:43 pm - 12:03 amMDW-PWM
9h 20m2 stops
Delta Logo
6:00 am - 12:28 pmPWM-MDW
7h 28m2 stops
$247Delta
Find Deal
Thu, Sep 4 - Tue, Sep 9
Southwest Logo
2:10 pm - 8:00 pmMDW-PWM
4h 50m1 stop
Southwest Logo
10:30 am - 12:00 pmPWM-MDW
2h 30mnonstop
$248Southwest
Find Deal
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.

If you are looking for a flight deal from Chicago Midway Airport to Portland, look for departures on Tuesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Portland, Thursday is the cheapest day to fly and Saturday is the most expensive.

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 $348, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$100
Best time to beat the crowds with an average 51% drop 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 $100 for a one-way ticket and $217 for a round-trip.

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

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

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

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Portland is Portland.

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

    Only American Airlines offers 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 Embraer 175 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 PWM 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 $215 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 4241 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
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.

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

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