PWM - MDW

$115 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 12/3. 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 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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Everything you should know

Cheapest round-trip
$249
Delta
Thu 2/26Mon 3/2
PWM - MDW • 1 stop
Cheapest one-way
$115
Southwest
Wed 12/3
PWM - MDW • 1 stop
Top airlines
Delta
Cheapest • from $249 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
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+1
Airline reviews
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight 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, Feb 26 - Mon, Mar 2
Delta Logo
5:30 am - 12:01 pmPWM-MDW
7h 31m1 stop
Delta Logo
1:05 pm - 9:59 pmMDW-PWM
7h 54m1 stop
$249Delta
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Wed, Nov 12 - Sun, Nov 16
Delta Logo
2:30 pm - 11:40 pmPWM-MDW
10h 10m2 stops
Delta Logo
6:00 am - 12:30 pmMDW-PWM
5h 30m1 stop
$254Delta
Find Deal
Sat, Jan 24 - Fri, Jan 30
Delta Logo
6:17 am - 3:40 pmPWM-MDW
10h 23m2 stops
Delta Logo
12:48 pm - 12:20 amMDW-PWM
10h 32m2 stops
$259Delta
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Tue, Nov 11 - Thu, Nov 13
Delta Logo
6:00 am - 11:52 amPWM-MDW
6h 52m1 stop
Delta Logo
9:34 am - 4:07 pmMDW-PWM
5h 33m1 stop
$269Delta
Find Deal
Thu, Nov 13 - Mon, Nov 17
Delta Logo
6:00 am - 4:38 pmPWM-MDW
11h 38m2 stops
Delta Logo
6:00 am - 12:30 pmMDW-PWM
5h 30m1 stop
$274Delta
Find Deal
Fri, Dec 12 - Mon, Dec 15
Southwest Logo
11:50 am - 7:05 pmPWM-MDW
8h 15m2 stops
Southwest Logo
5:35 am - 2:55 pmMDW-PWM
8h 20m2 stops
$289Southwest
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Thu, Nov 13 - Mon, Nov 17
Southwest Logo
3:00 pm - 8:40 pmPWM-MDW
6h 40m1 stop
Southwest Logo
6:40 am - 12:10 pmMDW-PWM
4h 30m1 stop
$299Southwest
Find Deal
Sat, Jan 24 - Fri, Jan 30
Multiple Airlines Logo
11:02 am - 11:25 pmPWM-MDW
13h 23m2 stops
Multiple Airlines Logo
8:56 pm - 10:22 amMDW-PWM
12h 26m1 stop
$309Multiple Airlines
Find Deal
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
5:25 am - 1:20 pmPWM-MDW
8h 55m1 stop
Southwest Logo
8:45 pm - 1:45 pmMDW-PWM
16h 00m2 stops
$315Southwest
Find Deal
Sun, Jan 25 - Fri, Jan 30
Southwest Logo
5:35 am - 12:05 pmPWM-MDW
7h 30m1 stop
Southwest Logo
6:50 am - 2:55 pmMDW-PWM
7h 05m1 stop
$359Southwest
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 Sunday is the most expensive. Flying from Chicago Midway Airport back to Portland, the best deals are generally found on Tuesday, with Thursday 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 $417, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$115
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 $115 for a one-way ticket and $249 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.

  • Which airline alliances offer flights from Portland to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Portland and Chicago Midway Airport.

  • 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 7.9.

  • 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 $278 or less one-way and $578 or less round-trip.

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 4241 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

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

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