Book Cheap Flights from Toronto to Chicago starting from C$138

Chicago in the United States offers a compelling blend of cultural depth, historical importance, and access to significant natural features, drawing travellers from Toronto and beyond. Whether your interest lies in groundbreaking architecture, exploring a profound musical heritage, or enjoying lakeside views, this city presents a wealth of experiences. It’s a destination rich in discovery, from its famed museums to its diverse neighbourhoods.

Flights from Toronto to Chicago generally take around 1 hour and 30 minutes, making it a convenient trip for a quick getaway or a longer visit. For an ideal travel experience, consider visiting during the spring or fall. These seasons offer pleasant weather for exploring the city's outdoor attractions and events. While summer is also popular, it can be hotter and more crowded. Winter travel might appeal to those seeking indoor cultural activities and fewer tourists, though colder temperatures are to be expected. Travellers can find a range of flight options throughout the year, with numerous daily departures connecting the two cities.

Toronto operates two main airports for travellers embarking on a flight journey to Chicago. Each offers distinct options for your discovery towards this destination.

Toronto Pearson International Airport (YYZ)

This is the largest and busiest airport in Toronto, located approximately 25 kilometres northwest of the city centre. It serves as a major hub for international and domestic flights, connecting passengers to a vast array of destinations, including frequent services to Chicago. Accessibility is well-managed through various public transit options and car rental facilities.

Billy Bishop Toronto City Airport (YTZ)

Situated on an island just offshore from downtown Toronto, Billy Bishop Toronto City Airport offers a convenient option, particularly for those starting their journey within the urban core. A quick ferry crossing or pedestrian tunnel connects travellers directly to the airport. It primarily handles regional flights, with regular connections to Chicago, focusing on a more streamlined travel experience.

Your journey from Toronto to Chicago offers several arrival points. Chicago is served by two main commercial airports, facilitating seamless travel into the region.

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport is a major global air hub, located approximately 25 kilometres northwest of downtown Chicago. It serves as a primary gateway for both domestic and international flights, providing extensive connectivity to various destinations. Travellers can access the city centre directly via the CTA Blue Line train service, which runs 24 hours a day, or through numerous bus and car rental options.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport is situated closer to the city centre, about 15 kilometres southwest of downtown Chicago. This airport primarily handles domestic flights and offers a convenient alternative for travellers heading to the south side of the city or needing quicker access to downtown. The CTA Orange Line train provides direct public transit to the Loop, complementing other ground transport choices like car rental and ride-share services.

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