$104 Cheap Flights from Chicago (MDW) to Portland (PWM)

View $104 flight on Sun, May 11, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Portland (MDW-PWM)

Prices were available within the past 7 days and start at $104 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, May 24 - Wed, May 28
MDW
Chicago
PWM
Portland
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 24 from Chicago to Portland, returning Wed, May 28, priced at $217 found 1 day ago
Frontier Airlines
Sun, May 4 - Sat, May 10
MDW
Chicago
PWM
Portland
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 4 from Chicago to Portland, returning Sat, May 10, priced at $218 found 1 day ago
Delta
Wed, Jun 25 - Mon, Jun 30
MDW
Chicago
PWM
Portland
$219 Roundtrip, found 3 hours ago
$219
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Jun 25 from Chicago to Portland, returning Mon, Jun 30, priced at $219 found 3 hours ago
Delta
Wed, Jun 25 - Wed, Jul 2
MDW
Chicago
PWM
Portland
$223 Roundtrip, found 1 day ago
$223
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 25 from Chicago to Portland, returning Wed, Jul 2, priced at $223 found 1 day ago
Frontier Airlines
Sun, May 4 - Thu, May 8
MDW
Chicago
PWM
Portland
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 4 from Chicago to Portland, returning Thu, May 8, priced at $228 found 1 day ago
Southwest Airlines
Tue, Sep 16 - Sat, Sep 20
MDW
Chicago
PWM
Portland
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Portland, returning Sat, Sep 20, priced at $229 found 3 days ago
Delta
Sat, Jul 19 - Wed, Jul 23
MDW
Chicago
PWM
Portland
$229 Roundtrip, found 4 hours ago
$229
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Jul 19 from Chicago to Portland, returning Wed, Jul 23, priced at $229 found 4 hours ago
Frontier Airlines
Fri, May 23 - Sat, Jun 7
MDW
Chicago
PWM
Portland
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 23 from Chicago to Portland, returning Sat, Jun 7, priced at $230 found 2 days ago
Delta
Tue, Jun 10 - Wed, Jul 2
MDW
Chicago
PWM
Portland
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 10 from Chicago to Portland, returning Wed, Jul 2, priced at $233 found 1 day ago
Delta
Sat, Sep 13 - Wed, Sep 17
MDW
Chicago
PWM
Portland
$234 Roundtrip, found 2 days ago
$234
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 13 from Chicago to Portland, returning Wed, Sep 17, priced at $234 found 2 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) cost?
Discover the latest flight deals from MDW to PWM by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to PWM?
The cheapest flights from MDW to PWM are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
You can’t catch a direct flight to Portland Intl. Jetport Airport (PWM) from Chicago, IL (MDW-Midway Intl.). However, you can easily travel to Portland without any layovers by departing from O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from MDW to PWM?
At the moment, the cheapest carrier offering one-way flights from MDW to PWM is Southwest Airlines. You can take off on this route from $169. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on June 11 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
There aren’t any daily nonstop flights departing from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you’ll be cruising above the clouds in no time at all.
What day of the week has the most flights from MDW to PWM?
Typically you’ll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from MDW to PWM?
Consider traveling with Southwest Airlines if you’d like to go straight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) without any holdups. This carrier has the best track record for punctuality, with an on-time performance of 87%. Want to be updated if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
Book a flight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) that takes off before 3 PM to reduce the likelihood of delays. Departures after this hour are on average 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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) last-minute?
Waiting until just before your departure to book your flight from MDW to PWM generally means paying more. While you might find some last-minute discounts, there’s no guarantee. Be flexible with your itinerary to boost your chances of scoring a bargain.
Is it cheaper to book a MDW to PWM flight and hotel package?
Opting for a MDW to PWM flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our extensive range of accommodations and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
Generally, it’s possible to cancel or reschedule your MDW to PWM flight. However, if it’s been more than 24 hours since booking, additional fees may apply. Check your airline’s policies in your itinerary to see what changes are allowed and if any costs are involved. You’ll also find more details on our Customer Service portal.
*Available to One Key members.