Create your free account
Sign in to your account
Search over 590,000 properties worldwide and 550 airlines worldwide.
No Expedia cancellation fee to change or cancel almost any hotel reservation.
Find cheap flights from Toronto (YYZ) to Chicago (ORD)
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Top Routes from Toronto
- Toronto to Shanghai (YYZ - PVG)
- Toronto to Calgary (YYZ - YYC)
- Toronto to London (YYZ - LCY)
- Toronto to Bangkok (YYZ - BKK)
- Toronto to Hong Kong (YYZ - HKG)
- Toronto to Paris (YYZ - CDG)
- Toronto to New York (YYZ - LGA)
- Toronto to Manila (YYZ - MNL)
- Toronto to Delhi (YYZ - DEL)
- Toronto to London (YYZ - STN)
- Toronto to Dublin (YYZ - DUB)
- Toronto to Rome (YYZ - FCO)
Top Routes to Chicago
- Ottawa to Chicago (YOW - ORD)
- Newark to Chicago (EWR - ORD)
- Calgary to Chicago (YYC - ORD)
- Burlington to Chicago (BTV - ORD)
- Detroit to Chicago (DTW - ORD)
- New York to Chicago (LGA - ORD)
- Winnipeg to Chicago (YWG - ORD)
- Halifax to Chicago (YHZ - ORD)
- Quebec to Chicago (YQB - ORD)
- Victoria to Chicago (YYJ - ORD)
- Seattle to Chicago (SEA - ORD)
- New York to Chicago (JFK - ORD)
Toronto to Chicago Flights
Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Toronto to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from YYZ to ORD and begin your journey!
Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Toronto to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.
Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from YYZ to ORD. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.
Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!
