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Cheap round-trip flights to Chicago

These prices were available within the past 7 days. Prices quoted are per person, return, 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 C$262.44, 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!

Chicago Flight + Hotel Deals

Reviews from verified customers

Jan 19, 2018

Expedia was a pain - it doesn't provide the actual flight details when the carrier (actual United Airline flight) is not the the booking airline which was Air Canada.

Jan 18, 2018

Overall good service but hate the ergonomics of the chair. Super uncomfortable

Jan 17, 2018

1 hr delay @ ORD

Jan 14, 2018

The food was terrible

Jan 13, 2018

Good crew!

Jan 12, 2018

Landing in Chicago with bad weather conditions the pilots did a remarkable job.You should give them a raise in pay. Highly skilled professionals!!

Jan 12, 2018

waffle cookie was great

Jan 11, 2018

A light dinner should be offered for flights longer than 3 hours, instead of a bag of pretzels.

Jan 10, 2018

Baggage got 3 hours late to my final destination

Jan 8, 2018

Seriously the cute guy I was seated beside :)