Cheap Flights from Toronto to Chicago

Flight information Toronto to Chicago

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 703 kilometers

1h 40min

Most popular airline last month

Air Canada

Chicago O'Hare International, Chicago Pal-Waukee, Chicago Dupage County, Chicago Midway and others

5 airports

Flying out of Toronto

Toronto Pearson International Airport (YYZ) is a busy international airport serving Canada’s largest city. It is located 22.5 km from the city center. Billy Bishop Toronto City Airport is a smaller airport on the Toronto Islands which also sees international and domestic traffic. Direct flights from Toronto to Chicago depart from both airports. Main airlines flying this route include Porter Airlines, United, and Air Canada. You can find the cheapest flights from Toronto to Chicago by using Skyscanner’s flight search feature. All you have to do is tell it when you want to fly. If you know when you want to fly, sign up for price alerts from Skyscanner. You will receive notifications when the price of your chosen flight rises or falls so you can monitor fare fluctuations to get the best price on your tickets to Chicago from Toronto.

You can get to Billy Bishop Toronto City Airport by taking the ferry or walking through the pedestrian tunnel. You can get to Toronto Pearson International by taking the UP Express train, a public bus, taxi, or private car. Rental cars can be returned to the car rental companies with service at the airport. Passengers are asked to check in at least two hours before an international flight, but this can vary by airline. Canadians traveling to Chicago must present a passport valid for the duration of stay in the country. Both airports have food and beverage options, and Toronto Pearson offers currency exchange and free wi-fi throughout. Download Skyscanner’s mobile app to stay connected to the best travel deals no matter where you go.

Arriving in Chicago

Chicago O’Hare International Airport (ORD) is the primary airport serving the Chicago area. It is located 27 km northwest of the Loop. Midway International Airport (MDW) also takes international and domestic flights and is only 13 km from the Loop. Flights from Toronto may arrive at either airport. Passengers arriving from Canada will go through customs and immigration here. You can get from Chicago O’Hare to the city by taking the CTA blue line, the Metra, a taxi, shuttle, or private car. You can get to the city from Midway International by taking the CTA orange line or one of nine buses with service to Midway Airport. Taxis and private cars are always an option. Both airports have options for food and beverages.

Chicago’s humid continental climate is not much different from Toronto’s, with four distinct seasons including hot summers and cold winters. If you are flying in the winter be aware that winter weather may disrupt flights and cause delays. Toronto is one hour ahead of Chicago, so jet lag should not be a significant problem. I general, prices for similar goods and services are lower in Toronto than in Chicago.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.