Toronto (YYZ) to Chicago (ORD) flights
3 airlines fly nonstop from Toronto (YYZ) to Chicago (ORD): Air Canada, American Airlines and United Airlines. The two airports are 436 miles (702 km) apart. Air Canada and United Airlines are in Star Alliance and American Airlines is in oneworld. There are also 22 ways to fly it with one stop, through Detroit, Cleveland and Columbus and more.
Airlines flying nonstop from YYZ to ORD
- Air CanadaStar Alliance · bookable with 12 programsWho books it
- American Airlinesoneworld · bookable with 9 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book YYZ to ORD with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Air Canada AeroplanBooks Air Canada, United Airlines
- Air New Zealand AirpointsBooks Air Canada, United Airlines
- ANA Mileage ClubBooks Air Canada, United Airlines
- Avianca LifeMilesBooks Air Canada, United Airlines
- Emirates SkywardsBooks Air Canada, United Airlines
- EVA Air Infinity MileageLandsBooks Air Canada, United Airlines
- Lufthansa Miles & MoreBooks Air Canada, United Airlines
- Singapore Airlines KrisFlyerBooks Air Canada, United Airlines
- TAP Miles&GoBooks Air Canada, United Airlines
- Thai Royal Orchid PlusBooks Air Canada, United Airlines
- Turkish Airlines Miles&SmilesBooks Air Canada, United Airlines
- United MileagePlusBooks Air Canada, United Airlines
- Alaska Atmos RewardsBooks American Airlines
- American AAdvantageBooks American Airlines
- British Airways ClubBooks American Airlines
- Cathay Pacific Asia MilesBooks American Airlines
- Finnair PlusBooks American Airlines
- Iberia ClubBooks American Airlines
- JAL Mileage BankBooks American Airlines
- JetBlue TrueBlueBooks United Airlines
- Qantas Frequent FlyerBooks American Airlines
- Qatar Airways Privilege ClubBooks American Airlines
YYZ to ORD with one stop
22 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Cleveland (CLE)Air Canada, then American Airlines and United Airlines
- Via Columbus (CMH)Air Canada, then American Airlines and United Airlines
- Via Indianapolis (IND)Air Canada, then American Airlines and United Airlines
- Via Pittsburgh (PIT)Air Canada, then American Airlines and United Airlines
- Via Cincinnati (CVG)Air Canada, then American Airlines and United Airlines
- Via Ottawa (YOW)Air Canada, WestJet and 1 more, then United Airlines
- Via Saint Louis (STL)Air Canada, then American Airlines and United Airlines
- Via Dulles (IAD)United Airlines the whole way
- Via Washington (DCA)American Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines and Sun Country Airlines the whole way
+1 - Via Philadelphia (PHL)American Airlines the whole way
- Via Nashville (BNA)Air Canada and WestJet, then American Airlines and United Airlines
- Via Montreal (YUL)Air Canada the whole way
+2 - Via New York (EWR)United Airlines the whole way
YYZ to ORD: common questions
Which airlines fly nonstop from YYZ to ORD?
Air Canada (Star Alliance), American Airlines (oneworld) and United Airlines (Star Alliance) fly nonstop from Toronto (YYZ) to Chicago (ORD).
How far is Toronto from Chicago by plane?
Toronto (YYZ) and Chicago (ORD) are 436 miles (702 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book YYZ to ORD award flights?
22 programs can book at least one of the nonstop airlines: Air Canada Aeroplan, Air New Zealand Airpoints, ANA Mileage Club, Avianca LifeMiles, Emirates Skywards, EVA Air Infinity MileageLands, Lufthansa Miles & More, Singapore Airlines KrisFlyer and 14 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does YYZ to ORD cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for YYZ to ORD with taxes and fees.
Where can I connect between Toronto and Chicago?
The most direct connections are through Detroit (DTW), Cleveland (CLE), Columbus (CMH), Indianapolis (IND) and Pittsburgh (PIT). On 11 of them the same airline flies both flights, for example Delta Air Lines through Detroit.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.