Cheap Flights from Chicago to Toronto — $98

The route Chicago — Toronto is served by many carriers — 5 in total, including Air Canada, Porter Airlines, Passaredo Linhas Aereas, Air Transat, and American Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $98) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.

Chicago is served primarily by two major airports with distinct roles. O’Hare International (ORD) is the city’s international hub and a major transfer point for global and domestic carriers, typically handling full-service airlines and many long-haul routes; it sits about 17 miles northwest of downtown and is usually reached in 30–60 minutes by car depending on traffic. Public transit via the CTA Blue Line takes roughly 45–60 minutes with modest fares, while airport shuttles and taxis can be quicker but pricier. Midway (MDW) is a smaller, more budget-oriented airport about 10 miles southwest, commonly favored by low-cost carriers and short-haul flights; travel to downtown is often 20–40 minutes by car and 30–40 minutes by CTA Orange Line. O’Hare offers broader connections but can be busier and involve longer transfers; Midway can be simpler and cheaper for domestic trips but has fewer international options.

Toronto is primarily served by Toronto Pearson International (YYZ) and the smaller Billy Bishop Toronto City Airport (YTZ). Pearson is the city’s main international hub, typically handling most long-haul and legacy-carrier flights and often used by Air Canada and other global airlines; fares there can be mid-to-high relative to budget-centric airports. Located about 22 km northwest of downtown, travel options include the UP Express train (around 25 minutes, fares usually in the moderate range), taxis or rideshares (30–45 minutes depending on traffic, higher cost), and public buses. Pros: wide route network and full facilities; cons: can be busy with longer transfer times. Billy Bishop on the Toronto Islands is a compact, downtown-proximate airport favored by regional and low-cost carriers for short-haul trips. It sits roughly 2–3 km from the central business district and can be reached by a short ferry or pedestrian tunnel (5–15 minutes) or by taxi; fares are typically lower for short hop flights but service is limited. Pros: convenience and quick connections to downtown; cons: fewer destinations and restricted international capacity.

In different months, ticket prices from Chicago to Toronto vary: minimum — $95 (June 2026), maximum — $103 (July 2026). Typically, the flight costs $99–$201.