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How much is the cheapest round-trip flight to Chicago?

Prices were available within the past 7 days and starts at CA $138 for one-way flights and CA $226 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Trending flights to Chicago

Prices were available within the past 7 days and starts at CA $138 for one-way flights and CA $226 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

When you're ready to check out Chicago, depend on Expedia.ca! With plenty of cheap plane tickets to choose from, you can depend on more savings in your pocket to finally see what the place is all about. Book your affordable plane ticket today and see the town up close.

  • Come find out why Chicago is such a popular place to visit.
  • With flights as cheap as CA $226, make the right move and book your flight now.
  • Add a Chicago hotel to your flight and save money by purchasing a packaged deal!

Welcome to Chi-Town

When you touch down, we know you want to start seeing the sites ASAP. Luckily, you have many activities to pick from. For starters, check out our things to do guide and see for yourself that there are is no shortage of fun attractions in Chicago.

Hotels Near the Airport

If you need to rest before seeing the sites, you have several activities to choose from. In fact, there are 269 hotels to pick from. Best of all, the average rating of these accommodations is 4, so you can count on a cozy place to stretch out. In fact, you won't have trouble finding hotels which are all near the airport, so you can drop off your luggage and wash up before exploring the town.

There is No Better Time to Fly!

You can book your cheap flight from Expedia.ca year-round. Why wait any longer? Stuff your backpack and get to know Chicago for yourself!

Flights to Chicago information

Destination Airport Midway Intl.
Destination Airport IATA Code MDW
Destination City Name Chicago

Reviews from verified customers

Jan 17, 2020

Great experience so far

Jan 14, 2020

The flight is ok.

Jan 12, 2020

Like to fly through Air Canada

Jan 12, 2020

Great service!

Jan 10, 2020

Our check in experience was far from great. The first employee told us to check in at the kiosk, but it didn’t work and he suggested verbally to figure it out by ourselves... After, we went to the counter and the employee who helped us was not fast and he didn’t offer us to upgrade our seats and we would have paid for it. Once boarded in the plane, service was flawless!

Jan 10, 2020

Never turned on the WiFi. I needed to get some work done. dissapointed.

Jan 7, 2020

seats too close together. hard to work on a PC even if the person in front does not put their seat back. Flying has become bus travel but buses are more comfortable...

Jan 6, 2020

Delayed flight

Jan 2, 2020

Would have loved wifi or movie choices

Jan 2, 2020

Flight was good but Chicago airport and staff are a nightmare.