£163 Cheap Flights from Portland (PDX) to Chicago (MDW)

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Portland to Chicago. Operating between them 2 flights per day, 17 airlines cover the route. And Southwest Airlines fly direct, getting you to Midway Intl. in just 8hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Portland Intl. to Midway Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Portland Intl. (PDX) to Midway Intl. (MDW)

The easiest way to view the best deals on flights from Portland to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Portland Intl. to Midway Intl. start at just £412 and range up to £621.  

To find an even better deal, try  

• being flexible on your dates – midweek flights can be cheaper
• looking for other airports near Portland and Chicago
• booking your flight during August, the cheapest month on this route
• varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Portland to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Portland Intl. to Midway Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.