Cheap Flights from Toronto to Chicago — $225

Flights from Toronto to Chicago are operated by several airlines — United Airlines, American Airlines, and Porter Airlines. This allows passengers to flexibly choose flights based on departure time, cost, and additional services. The minimum ticket price starts at $225, making this destination accessible to travelers with different budgets. We help compare all available options in real time, so you can book tickets at the best value for money. The service ensures transparent search and lets you book affordable flights in just a few clicks.

The distance between Toronto and Chicago is 701km (435 miles). There are 238 direct flights from Toronto to Chicago. The time difference between Toronto and Chicago is 1h. Flights from Toronto begin at 6:00 AM. The latest flight from Toronto departs at 9:00 PM

Toronto is served primarily by Toronto Pearson International (YYZ) and Billy Bishop Toronto City (YTZ), with Pearson acting as the main international hub and Billy Bishop catering to regional and budget-conscious business travelers. Pearson typically hosts legacy carriers like Air Canada and many global airlines, as well as low-cost options, and can be perceived as mid-to-high priced for transfers and services. The airport is about 22 km (roughly 30–45 minutes by car depending on traffic) from downtown; options include the UP Express train (about 25 minutes, fares normally in the moderate range), taxis/ride-shares (30–60 minutes, fares vary), and shuttle services. Pros: extensive international connections and full-service facilities; Cons: can be busy with unpredictable checks and longer transfers. Billy Bishop sits on the Toronto Islands just 2 km from downtown (a short ferry or pedestrian tunnel access of 5–15 minutes) and is typically used by regional carriers and budget airlines for quick hops; it’s often seen as convenient and time-saving for central arrivals, though it offers fewer lounges and long-haul services.

Fly direct from Toronto to Chicago for the quickest, most convenient way to get between these two vibrant cities — fewer hassles, no layovers, and more time to enjoy your trip. While connecting options can occasionally be cheaper, a nonstop flight saves hours and delivers a more comfortable, reliable travel experience, making it worth considering when you book.

Chicago is served by two main airports with distinct roles. O'Hare International (ORD) is the city's primary international and connecting hub, typically hosting legacy carriers like United and American alongside many global airlines; fares from O'Hare can be competitive for long-haul and connecting itineraries. It's about 17–20 miles northwest of downtown; the CTA Blue Line offers direct service in roughly 45–50 minutes for a modest fare, while taxis or rideshares often take 30–60 minutes depending on traffic and can be pricier. Pros: extensive flight options and amenities; cons: busy terminals and potential for delays. Midway Airport (MDW) functions more as a domestic and leisure-focused airport, usually favored by low-cost and point-to-point carriers, notably Southwest, which can make it a budget-friendly choice for short-haul travel. Located roughly 10–12 miles southwest of the Loop, it’s connected by the CTA Orange Line in about 25–35 minutes with a similar low fare, and rideshares/taxis typically take 20–40 minutes. Pros: smaller terminals and quicker walk times; cons: fewer international routes and less frequent late-night service compared with O'Hare.

The cost of a one-way flight from Toronto to Chicago ranges from $96 (March 2026) to $117 (May 2026). On average, the ticket price is about $107–$117.