$76 Cheap Flights from Portland (PWM) to Chicago (MDW)

View $76 flight on Wed, Dec 3, 2025Opens in a new window

Popular airlines from Portland Intl. Jetport Airport (PWM) to Chicago Midway Airport (MDW)

Cheap Flights from Portland to Chicago (PWM-MDW)

Prices were available within the past 7 days and start at $76 for one-way flights and $190 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Dec 18 - Sun, Jan 11
PWM
Portland
MDW
Chicago
$190 Roundtrip, found 5 days ago
$190
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Dec 18 from Portland to Chicago, returning Sun, Jan 11, priced at $190 found 5 days ago
Southwest Airlines
Sat, Dec 6 - Sun, Dec 7
PWM
Portland
MDW
Chicago
$192 Roundtrip, found 6 days ago
$192
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Portland to Chicago, returning Sun, Dec 7, priced at $192 found 6 days ago
Southwest Airlines
Tue, Nov 18 - Wed, Dec 3
PWM
Portland
MDW
Chicago
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Portland to Chicago, returning Wed, Dec 3, priced at $201 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Sat, Oct 25
PWM
Portland
MDW
Chicago
$215 Roundtrip, found 6 days ago
$215
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Portland to Chicago, returning Sat, Oct 25, priced at $215 found 6 days ago
Delta
Tue, Nov 18 - Wed, Dec 3
PWM
Portland
MDW
Chicago
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 18 from Portland to Chicago, returning Wed, Dec 3, priced at $217 found 5 days ago
Delta
Thu, Jan 8 - Fri, Jan 23
PWM
Portland
MDW
Chicago
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Jan 8 from Portland to Chicago, returning Fri, Jan 23, priced at $222 found 6 days ago
Southwest Airlines
Tue, Nov 18 - Wed, Dec 3
PWM
Portland
MDW
Chicago
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Portland to Chicago, returning Wed, Dec 3, priced at $225 found 5 days ago
Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
PWM
Portland
MDW
Chicago
$225 Roundtrip, found 3 days ago
$225
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Portland to Chicago, returning Sat, Nov 1, priced at $225 found 3 days ago
Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
PWM
Portland
MDW
Chicago
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Portland to Chicago, returning Sat, Nov 1, priced at $235 found 3 days ago
Southwest Airlines
Sat, Nov 22 - Thu, Nov 27
PWM
Portland
MDW
Chicago
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Portland to Chicago, returning Thu, Nov 27, priced at $250 found 3 days ago

Frequently asked questions

How much does a flight from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $76 or cheap return flight from $190 from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW)?
Planning your trip for December can help you save, as it's the cheapest month for flights between PWM and MDW. You'll often find the lowest prices during the off-season.
What is the cheapest airline that flies from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest PWM to MDW flight.
How many flights per day from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW)?
Direct flights from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from PWM to MDW?
Usually you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW) route, fly before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Portland Intl. Jetport Airport (PWM)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Portland Intl. Jetport Airport (PWM). Check out your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a flight from PWM to MDW often results in higher prices. While you might find some last-minute offers, they aren't always guaranteed. Be flexible with your itinerary to boost your chances of landing a bargain.
Is it cheaper to book a PWM to MDW flight and hotel package?
Securing a PWM to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Pick from our wide range of hotels and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW)?
Usually, it's possible to reschedule or cancel your PWM to MDW flight. However, if it's been more than 24 hours since booking, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Portland Intl. Jetport
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$190
Distance
892 mi
Average flight time
2 hours 35 mins

Book with confidence

Book with confidence

Portland to Chicago Flights

The cheapest times to fly from Portland to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Chicago are during the month of December. You can find some of the cheapest flights from Portland to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Chicago

Sunday is one of the best days to book for cheap flights from Portland to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portland to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $76 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Portland to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.