Cheapest 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.

" YYZ Toronto to ORD Chicago $333.51 "

" YUL Montreal to MDW Chicago $369.67 "

" YTZ Toronto to MDW Chicago $380.17 "

" YOW Ottawa to MDW Chicago $428.51 "

" YEG Edmonton to ORD Chicago $436.58 "

" YTZ Toronto to ORD Chicago $440.71 "

" YOW Ottawa to ORD Chicago $454.67 "

" YYZ Toronto to MDW Chicago $469.94 "

" YHZ Halifax to MDW Chicago $485.03 "

" YYC Calgary to ORD Chicago $521.48 "

About Chicago

When you're ready to check out Chicago, depend on! 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 $333.51, 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 year-round. Why wait any longer? Stuff your backpack and get to know Chicago for yourself!

Explore Chicago

Heading to Chicago? Explore Chicago with Expedia's Travel Guides to find the best hotels, city breaks, car hire deals and more!

Alternative Nearby Airports

  • O'Hare Intl. (ORD)
  • Midway Intl. (MDW)