PWM - MDW

$99 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 9/2. 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, 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$289
Southwest
Fri 9/11Mon 9/14
PWM - MDW • 1 stop
Cheapest non-stop
$297
Southwest
Wed 7/8Wed 7/29
PWM - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $289 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Start a new search
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

Fri, Sep 11 - Mon, Sep 14
Southwest Logo
3:40 pm - 9:00 pm
PWM
-
MDW
6h 20m
1 stop
Southwest Logo
6:10 pm - 9:30 pm
MDW
-
PWM
2h 20mnonstop
$289Southwest
Wed, Jul 8 - Wed, Jul 29
Southwest Logo
7:30 am - 9:05 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
6:15 pm - 9:35 pm
MDW
-
PWM
2h 20mnonstop
$297Southwest
Sat, Sep 12 - Mon, Sep 14
Southwest Logo
5:40 am - 10:40 am
PWM
-
MDW
6h 00m
1 stop
Southwest Logo
2:35 pm - 10:25 pm
MDW
-
PWM
6h 50m
2 stops
$298Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
7:30 am - 9:05 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
6:15 pm - 9:35 pm
MDW
-
PWM
2h 20mnonstop
$302Southwest
Sat, Sep 12 - Mon, Sep 14
Southwest Logo
5:40 am - 1:05 pm
PWM
-
MDW
8h 25m
2 stops
Southwest Logo
5:30 am - 3:00 pm
MDW
-
PWM
8h 30m
2 stops
$303Southwest
Wed, Jul 8 - Wed, Jul 29
Southwest Logo
7:10 pm - 11:15 pm
PWM
-
MDW
5h 05m
1 stop
Southwest Logo
6:15 pm - 9:35 pm
MDW
-
PWM
2h 20mnonstop
$307Southwest
Wed, Jul 8 - Wed, Jul 29
Southwest Logo
7:30 am - 9:05 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
6:15 pm - 9:35 pm
MDW
-
PWM
2h 20mnonstop
$312Southwest
Tue, Jun 30 - Sat, Jul 4
Southwest Logo
5:30 am - 11:00 am
PWM
-
MDW
6h 30m
1 stop
Southwest Logo
7:40 am - 10:55 am
MDW
-
PWM
2h 15mnonstop
$317Southwest
Wed, Sep 23 - Sat, Sep 26
Southwest Logo
7:45 am - 9:20 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
3:20 pm - 6:35 pm
MDW
-
PWM
2h 15mnonstop
$318Southwest
Wed, Jul 8 - Wed, Jul 29
Southwest Logo
7:10 pm - 11:15 pm
PWM
-
MDW
5h 05m
1 stop
Southwest Logo
6:15 pm - 9:35 pm
MDW
-
PWM
2h 20mnonstop
$322Southwest
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, Tuesday 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 Saturday, with Sunday 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.

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 $378 on average.

Find deals

Good to know

Cheapest flight$99
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 5 days, the lowest price for a flight from Portland to Chicago Midway Airport was $99 for a one-way ticket and $289 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, Delta, and JetBlue 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 MAX 8 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.

  • 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 $197 or less one-way and $408 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

Reviews of the top airline 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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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

Information on your arrival and departure airports

Portland (PWM)
Midway (MDW)