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 7/2. 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

Thu, Aug 21 - Tue, Aug 26
Southwest Logo
10:35 am - 12:05 pmPWM-MDW
2h 30mnonstop
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
$245Southwest
Find Deal
Tue, Jul 1 - Tue, Jul 15
Delta Logo
12:49 pm - 6:41 pmPWM-MDW
6h 52m1 stop
Delta Logo
5:05 pm - 12:38 amMDW-PWM
6h 33m1 stop
$248Delta
Find Deal
Wed, Jul 2 - Wed, Jul 9
Delta Logo
12:49 pm - 6:41 pmPWM-MDW
6h 52m1 stop
Delta Logo
1:09 pm - 12:38 amMDW-PWM
10h 29m2 stops
$253Delta
Find Deal
Thu, Aug 21 - Tue, Aug 26
Southwest Logo
5:40 pm - 10:00 pmPWM-MDW
5h 20m1 stop
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
$255Southwest
Find Deal
Thu, Jul 3 - Sat, Jul 5
Southwest Logo
7:40 pm - 9:15 pmPWM-MDW
2h 35mnonstop
Southwest Logo
9:15 am - 12:30 pmMDW-PWM
2h 15mnonstop
$259Southwest
Find Deal
Thu, Aug 21 - Tue, Aug 26
Southwest Logo
5:50 am - 1:30 pmPWM-MDW
8h 40m2 stops
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
$260Southwest
Find Deal
Tue, Jul 1 - Wed, Jul 16
Delta Logo
12:49 pm - 6:41 pmPWM-MDW
6h 52m1 stop
Delta Logo
12:43 pm - 12:57 amMDW-PWM
11h 14m2 stops
$262Delta
Find Deal
Thu, Jul 3 - Sat, Jul 5
Southwest Logo
1:20 pm - 5:25 pmPWM-MDW
5h 05m1 stop
Southwest Logo
9:15 am - 12:30 pmMDW-PWM
2h 15mnonstop
$269Southwest
Find Deal
Tue, Jul 29 - Tue, Aug 5
Delta Logo
6:05 am - 12:29 pmPWM-MDW
7h 24m2 stops
Delta Logo
9:25 am - 4:11 pmMDW-PWM
5h 46m1 stop
$270Delta
Find Deal
Sun, Jun 29 - Wed, Jul 2
 Logo
12:46 pm - 9:44 amPWM-MDW
21h 58m2 stops
 Logo
9:03 am - 2:32 pmMDW-PWM
28h 29m2 stops
Useful Info

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 $318, prices are generally cheapest when you fly direct.

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 $245 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 737-800 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 $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 $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 $169 or less one-way and $294 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

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 4278 reviews
8.0Comfort
7.1Food
8.6Crew
7.6Entertainment
8.2Boarding
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

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