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Cheap Flights from Toronto (YTO) to Chicago (CHI)

Cheap Flights from Toronto to Chicago (YTO-CHI)

Prices were available within the past 7 days and start at AU$213 for one-way flights and AU$388 for return, for the period specified. Prices and availability are subject to change.
Porter Airlines
Wed, 11 Nov - Sun, 15 Nov
YTZ
Toronto
ORD
Chicago
AU$388
Return
Found 1 day ago
Select Porter Airlines flight, departing Wed, 11 Nov from Toronto to Chicago, returning Sun, 15 Nov, priced at AU$388 Found 1 day ago
Air Canada
Thu, 26 Nov - Mon, 30 Nov
YYZ
Toronto
ORD
Chicago
AU$397
Return
Found 1 day ago
Select Air Canada flight, departing Thu, 26 Nov from Toronto to Chicago, returning Mon, 30 Nov, priced at AU$397 Found 1 day ago
Air Canada
Wed, 11 Nov - Sun, 15 Nov
YHM
Hamilton
ORD
Chicago
AU$397
Return
Found 1 day ago
Select Air Canada flight, departing Wed, 11 Nov from Hamilton to Chicago, returning Sun, 15 Nov, priced at AU$397 Found 1 day ago
Air Canada
Wed, 11 Nov - Sun, 15 Nov
YKF
Kitchener
ORD
Chicago
AU$397
Return
Found 1 day ago
Select Air Canada flight, departing Wed, 11 Nov from Kitchener to Chicago, returning Sun, 15 Nov, priced at AU$397 Found 1 day ago
Air Canada
Thu, 26 Nov - Mon, 30 Nov
YYZ
Toronto
ORD
Chicago
AU$402
Return
Found 1 day ago
Select Air Canada flight, departing Thu, 26 Nov from Toronto to Chicago, returning Mon, 30 Nov, priced at AU$402 Found 1 day ago
Air Canada
Thu, 26 Nov - Mon, 30 Nov
YYZ
Toronto
ORD
Chicago
AU$406
Return
Found 1 day ago
Select Air Canada flight, departing Thu, 26 Nov from Toronto to Chicago, returning Mon, 30 Nov, priced at AU$406 Found 1 day ago
Air Canada
Wed, 11 Nov - Sun, 15 Nov
YTZ
Toronto
ORD
Chicago
AU$411
Return
Found 1 day ago
Select Air Canada flight, departing Wed, 11 Nov from Toronto to Chicago, returning Sun, 15 Nov, priced at AU$411 Found 1 day ago
American Airlines
Thu, 26 Nov - Mon, 30 Nov
YYZ
Toronto
ORD
Chicago
AU$418
Return
Found 1 day ago
Select American Airlines flight, departing Thu, 26 Nov from Toronto to Chicago, returning Mon, 30 Nov, priced at AU$418 Found 1 day ago
Delta
Sat, 7 Nov - Sun, 8 Nov
YYZ
Toronto
ORD
Chicago
AU$476
Return
Found 6 days ago
Select Delta flight, departing Sat, 7 Nov from Toronto to Chicago, returning Sun, 8 Nov, priced at AU$476 Found 6 days ago
WestJet
Thu, 3 Dec - Thu, 10 Dec
YYZ
Toronto
ORD
Chicago
AU$979
Return
Found 2 days ago
Select WestJet flight, departing Thu, 3 Dec from Toronto to Chicago, returning Thu, 10 Dec, priced at AU$979 Found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from AU$490
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from AU$490
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from AU$513
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from AU$513

Find the cheapest month to fly from Toronto (YTO) to Chicago (CHI)

October is typically the cheapest month to fly

From AU$304 - AU$570 per traveller.

Book with confidence

YTO to CHI Flights

Ready to get away? Use Expedia.com.au to book cheap flights from Toronto to Chicago AU$388, and have leftover money to spare on adventures and activities while you’re in town. We have the world’s largest selection of flights, not to mention lower airfares than you’ll find anywhere else on the Internet.

Our user-friendly tools make it easier than ever to book YTO to CHI flights, even if you’re hoping to hop aboard one of the last-minute flights leaving today. So whether you seek a spontaneous trip to this city’s hottest attractions, or prefer to plan out every detail of your adventure ahead of time, Expedia.com.au is here to help you find exactly what you are interested in.

If you’re on the hunt for cheap flights to Chicago from Toronto, you need not look any further. We make it simple for you to compare different airline carriers or choose the one that appeals to you most. We work with dozens of airlines in order to offer you incredible deals on business and personal travel. Start by searching through our selection of plane tickets today, and you’ll be in the sky before you know it.

Travel information

Origin airport
Billy Bishop Toronto City Airport
Destination airport
Chicago O'Hare International Airport
Distance
717 km away
Airlines serving
PD, Air Transat, Air Canada, United
Popular airline
PD
Return price
AU$388
Average flight time
2 hours 8 mins
*Available to Expedia members.