MDW - PWM

$115 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 3/15. 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
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Everything you should know

Cheapest round-trip
$229
Southwest
Thu 1/8Mon 1/12
MDW - PWM • 1 stop
Cheapest non-stop
$413
Southwest
Fri 6/12Mon 6/15
MDW - PWM • Non-stop
Top airlines
Southwest
Cheapest • from $229 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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Flight Deals
Booking Insights
Flight Deals

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

Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:50 am - 12:10 pm
MDW
-
PWM
4h 20m1 stop
Southwest Logo
5:45 am - 11:35 am
PWM
-
MDW
6h 50m1 stop
$229Southwest
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:50 am - 2:55 pm
MDW
-
PWM
7h 05m1 stop
Southwest Logo
12:45 pm - 6:35 pm
PWM
-
MDW
6h 50m2 stops
$234Southwest
Sat, Jan 10 - Sat, Jan 17
Delta Logo
9:32 am - 10:27 pm
MDW
-
PWM
11h 55m2 stops
Delta Logo
1:13 pm - 10:07 pm
PWM
-
MDW
9h 54m2 stops
$239Delta
Sat, Apr 11 - Mon, Apr 13
Southwest Logo
9:05 am - 4:00 pm
MDW
-
PWM
5h 55m1 stop
Southwest Logo
5:30 am - 12:05 pm
PWM
-
MDW
7h 35m1 stop
$249Southwest
Sat, Jan 24 - Fri, Feb 6
Delta Logo
1:26 pm - 10:27 pm
MDW
-
PWM
8h 01m2 stops
Delta Logo
5:30 am - 11:59 am
PWM
-
MDW
7h 29m1 stop
$254Delta
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
6:50 am - 12:10 pm
MDW
-
PWM
4h 20m1 stop
Southwest Logo
5:35 am - 12:05 pm
PWM
-
MDW
7h 30m1 stop
$274Southwest
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
9:50 am - 2:55 pm
MDW
-
PWM
4h 05m1 stop
Southwest Logo
5:35 am - 12:30 pm
PWM
-
MDW
7h 55m2 stops
$279Southwest
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
10:10 am - 10:15 pm
MDW
-
PWM
11h 05m2 stops
Southwest Logo
12:45 pm - 6:35 pm
PWM
-
MDW
6h 50m2 stops
$284Southwest
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
11:25 am - 6:30 pm
MDW
-
PWM
6h 05m2 stops
Southwest Logo
7:30 am - 9:05 am
PWM
-
MDW
2h 35mnonstop
$289Southwest
Fri, Jan 23 - Wed, Feb 4
Multiple Airlines Logo
1:00 pm - 10:22 am
MDW
-
PWM
20h 22m1 stop
Multiple Airlines Logo
6:18 pm - 11:45 am
PWM
-
MDW
18h 27m2 stops
$296Multiple Airlines
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 Thursday, as it's usually the priciest day. When flying back from Portland, Thursday is the cheapest day to fly and Sunday 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.

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 $384 on average.

Find deals

Good to know

Cheapest flight$115
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 $115 for a one-way ticket and $229 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 Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Portland flight route.

  • 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.

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.
7.9
SouthwestOverall score based on 4250 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

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 you need to know for your flight from Midway to Portland

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Portland (PWM)