Cheap Alaska Airlines flights from Portland to Chicago (PDX to MDW)

Discover our best Alaska Airlines flight from Portland PDX to Chicago MDW 

To find the best deals on flights to Portland from Chicago with Alaska Airlines, just enter your travel dates, filter by Alaska Airlines, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

Return flights from Portland PDX to Chicago MDW with Alaska Airlines 

If you’re planning a round trip, booking return flights with Alaska Airlines is usually the most cost-effective option. With airfares ranging from to , it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

Book one-way Alaska Airlines flights from Portland PDX to Chicago MDW 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way Alaska Airlines flight from Portland to Chicago costs from . Prices and availability subject to change. Additional terms may apply. 

The easy way to find cheap flights to Chicago MDW from  Portland PDX with Alaska Airlines 

To find a cheap Alaska Airlines flight from Portland PDX to Chicago MDW, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

How to find our best airfare deals on Alaska Airlines flights from Portland PDX to Chicago MDW 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as , or if you book a flight with a stopover. 

Find nonstop flights from Portland PDX to Chicago MDW with Alaska Airlines 

If you’re keen to be on Chicago soil fast, don’t waste time with a stopover—filter your search results to show direct Alaska Airlines flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

Flexible airline tickets for Alaska Airlines flights from Portland PDX to Chicago MDW 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

There are a lot of reasons to book your flights to Chicago MDW from  Portland PDX with Alaska Airlines on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.