S$127 Cheap Flights from Chicago to Toronto

View S$127 flight on Wed, 29 Jul, 2026Opens in a new window

Popular airlines from Chicago to Toronto

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 40% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Toronto (CHI-YTO)

Prices were available within the past 7 days and start at S$127 for one-way flights and S$324 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 5 Jun - Sun, 7 Jun
ORD
Chicago
YYZ
Toronto
S$324 Return, found 5 days ago
S$324
Return
found 5 days ago
Select Delta flight, departing Fri, 5 Jun from Chicago to Toronto, returning Sun, 7 Jun, priced at S$324 found 5 days ago
United
Fri, 5 Jun - Sun, 7 Jun
ORD
Chicago
YYZ
Toronto
S$330 Return, found 5 days ago
S$330
Return
found 5 days ago
Select United flight, departing Fri, 5 Jun from Chicago to Toronto, returning Sun, 7 Jun, priced at S$330 found 5 days ago
Air Canada
Fri, 5 Jun - Sun, 7 Jun
ORD
Chicago
YYZ
Toronto
S$331 Return, found 5 days ago
S$331
Return
found 5 days ago
Select Air Canada flight, departing Fri, 5 Jun from Chicago to Toronto, returning Sun, 7 Jun, priced at S$331 found 5 days ago
Delta
Fri, 5 Jun - Sun, 7 Jun
ORD
Chicago
YYZ
Toronto
S$334 Return, found 5 days ago
S$334
Return
found 5 days ago
Select Delta flight, departing Fri, 5 Jun from Chicago to Toronto, returning Sun, 7 Jun, priced at S$334 found 5 days ago
Air Canada
Fri, 5 Jun - Sun, 7 Jun
ORD
Chicago
YTZ
Toronto
S$335 Return, found 5 days ago
S$335
Return
found 5 days ago
Select Air Canada flight, departing Fri, 5 Jun from Chicago to Toronto, returning Sun, 7 Jun, priced at S$335 found 5 days ago
Air Canada
Fri, 5 Jun - Sun, 7 Jun
ORD
Chicago
YYZ
Toronto
S$335 Return, found 5 days ago
S$335
Return
found 5 days ago
Select Air Canada flight, departing Fri, 5 Jun from Chicago to Toronto, returning Sun, 7 Jun, priced at S$335 found 5 days ago
Air Canada
Wed, 6 May - Sat, 9 May
ORD
Chicago
YYZ
Toronto
S$336 Return, found 4 days ago
S$336
Return
found 4 days ago
Select Air Canada flight, departing Wed, 6 May from Chicago to Toronto, returning Sat, 9 May, priced at S$336 found 4 days ago
Air Canada
Fri, 31 Jul - Sun, 2 Aug
ORD
Chicago
YTZ
Toronto
S$339 Return, found 5 days ago
S$339
Return
found 5 days ago
Select Air Canada flight, departing Fri, 31 Jul from Chicago to Toronto, returning Sun, 2 Aug, priced at S$339 found 5 days ago
Porter Airlines
Fri, 8 May - Sun, 10 May
MDW
Chicago
YTZ
Toronto
S$342 Return, found 4 days ago
S$342
Return
found 4 days ago
Select Porter Airlines flight, departing Fri, 8 May from Chicago to Toronto, returning Sun, 10 May, priced at S$342 found 4 days ago
American Airlines
Sat, 9 May - Sun, 10 May
ORD
Chicago
YYZ
Toronto
S$423 Return, found 5 days ago
S$423
Return
found 5 days ago
Select American Airlines flight, departing Sat, 9 May from Chicago to Toronto, returning Sun, 10 May, priced at S$423 found 5 days ago

Frequently asked questions

How much is a flight from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
The lowest price advertised for a round-trip flight from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) is S$324. But you better act soon. This price is taken from fares offered within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
The majority of flights can be conveniently cancelled online, but whether or not you incur a fee all comes down to your airline. If you do need to cancel your escape, follow the instructions in the Customer Service Portal.
How do I find cheap flights from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
That new movie you've been wanting to see will just have to wait — the flight distance between Chicago, IL (CHI-All Airports) (CHI) and Toronto (YTO-All Airports) (YTO) is only 740 kilometres. The captain will be instructing you to put your seat upright for landing before you know it.
Which airlines fly direct from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
It's easy to fly directly from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports). Here are the most sought-after carriers that operate nonstop services on this route:

  • American Airlines - (AA) with 152 monthly flights
  • United Airlines - (UA) with 147 monthly flights
  • Air Canada - (AC) with 147 monthly flights
  • Porter Airlines - (PD) with 82 monthly flights

Are Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) can be hit-or-miss. You might be lucky and score a bargain, but then again, you could miss out entirely! If you'd prefer to start your trip planning early, Expedia compares flight deals up to a year in advance. Just bear in mind that not all airlines advertise their prices so far in advance. Our suggestion? Check back often as prices are updated frequently.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Pearson Intl.
Airlines serving
Air Canada
Return price
S$323
Distance
697 km

Explore a world of travel with Expedia

*Available to Expedia members.