$79 Cheap flights from Portland Intl. Jetport to Midway Intl. (PWM to MDW)

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly from Portland Intl. Jetport to Midway Intl.

Amazing PWM to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $138 round trip and $79 one way. Prices and availability subject to change. Additional terms may apply.

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North
Hotel Riu Plaza Chicago
Fairmont Chicago at Millennium Park
The Emily Hotel
Sable at Navy Pier Chicago, Curio Collection by Hilton
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Traveling From
Portland Intl. Jetport
Traveling To
Midway Intl.
Shortest Flight Time
hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$138

Route Info

Flight path for flights from Portland International Jetport to Chicago Midway International Airport.


Distance:
1,066.00 miles


Discover our best flights from Portland PWM to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Portland PWM to Chicago MDW at the right price  

Airfares to Chicago MDW from Portland PWM currently cost between $138 and $243. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Portland PWM to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Portland PWM to Chicago MDW on Travelocity starting at $79. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago MDW from Portland PWM quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from PWM to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Portland PWM to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from PWM. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Portland PWM to Chicago MDW today 

If you’re flexible about when you travel, December is usually the cheapest month to fly from Portland PWM to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago MDW from Portland PWM 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from PWM have this option.  

 

Travel with confidence when you book flights to Chicago MDW from Portland PWM with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.