PWM - MDW

$90 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 7/1. 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

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 Flight Deals 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.

Recent round-trip flight deals from Portland to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Portland to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
5:30 am - 11:53 amPWM-MDW
7h 23m1 stop
Delta Logo
9:24 am - 4:15 pmMDW-PWM
5h 51m1 stop
$229Delta
Find Deal
Tue, Jun 3 - Tue, Jun 17
Delta Logo
6:05 am - 12:28 pmPWM-MDW
7h 23m2 stops
Delta Logo
1:08 pm - 11:59 pmMDW-PWM
9h 51m2 stops
$233Delta
Find Deal
Thu, May 29 - Tue, Jun 3
Delta Logo
5:30 am - 12:28 pmPWM-MDW
7h 58m2 stops
Delta Logo
4:15 pm - 11:59 pmMDW-PWM
6h 44m1 stop
$234Delta
Find Deal
Tue, Jun 3 - Sat, Jun 7
Delta Logo
11:33 am - 6:45 pmPWM-MDW
8h 12m2 stops
Delta Logo
1:08 pm - 11:59 pmMDW-PWM
9h 51m2 stops
$239Delta
Find Deal
Tue, Jun 3 - Sat, Jun 7
Delta Logo
5:30 am - 11:53 amPWM-MDW
7h 23m1 stop
Delta Logo
1:09 pm - 12:26 amMDW-PWM
10h 17m2 stops
$244Delta
Find Deal
Wed, Jun 4 - Sun, Jun 8
Southwest Logo
5:50 pm - 11:25 pmPWM-MDW
6h 35m1 stop
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
$249Southwest
Find Deal
Wed, Jul 30 - Tue, Aug 5
Southwest Logo
7:55 pm - 9:30 pmPWM-MDW
2h 35mnonstop
Southwest Logo
6:10 pm - 11:25 pmMDW-PWM
4h 15m1 stop
$254Southwest
Find Deal
Sun, Jun 8 - Tue, Jun 10
Delta Logo
6:05 am - 12:28 pmPWM-MDW
7h 23m2 stops
Delta Logo
4:15 pm - 11:59 pmMDW-PWM
6h 44m1 stop
$268Delta
Find Deal
Thu, May 29 - Tue, Jun 3
Delta Logo
1:15 pm - 6:41 pmPWM-MDW
6h 26m1 stop
Delta Logo
4:26 pm - 12:26 amMDW-PWM
7h 00m1 stop
$269Delta
Find Deal
Sat, Jun 14 - Mon, Jun 16
Delta Logo
6:03 am - 12:29 pmPWM-MDW
7h 26m2 stops
Delta Logo
4:26 pm - 12:26 amMDW-PWM
7h 00m1 stop
$274Delta
Find Deal
Sat, Jun 14 - Mon, Jun 16
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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, Wednesday 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 Friday being the most expensive.

Good to know

Cheapest flight$90
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 $90 for a one-way ticket and $229 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 Boeing 737-700 Passenger/BBJ1 (winglets) 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?

    You can catch a nonstop flight from Portland to Chicago Midway Airport on Monday, Thursday, Friday, and Saturday.

  • 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 $371 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 $343 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 $193 or less one-way and $356 or less round-trip.

Prefer to fly direct from Portland to Chicago Midway Airport?

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
See more direct flights

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 4294 reviews
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

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

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