C$ 189 Find Cheap Flights from Toronto to Chicago – Compare and Save

These are the earliest and latest flight times available from Toronto to Chicago:

• Earliest: departs at 6:45 am and lands at 8:58 am
• Latest: departs at 7:40 pm and lands at 9:53 pm.

The flight takes about 2h 13m.

Four cabin classes are available on flights from Toronto to Chicago:

• Economy Class
• Premium Economy Class
• Business Class
• First Class

Prices vary by airline.

A direct flight from Toronto to Chicago takes 2h 13m, covering 1,127 km.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Round-trip flights from Toronto to Chicago range from C$ 315 to C$ 518, with an average of C$ 394 over the past 12 months. Anything below C$ 315 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 61% above the C$ 394 route average. Book 26 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than direct options on average. Layover fares average C$ 283 round-trip via Charlotte Douglas (CLT), compared to C$ 394 for direct.

United Airlines is slightly above the route average for timely arrivals, while American Airlines has a lower on-time arrival rate. On-time arrival rates on Toronto to Chicago flights are:

• United Airlines: 91% on time
• American Airlines: 87% on time
• Air Canada: 80% on time

On average, flights on this route are punctual 87% of the time.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 34–C$ 140 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

Morning is the busiest departure period on Toronto to Chicago flights, with 39% leaving in that window. Afternoon departures account for 39%, Evening flights for 22%, and Night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 298 to C$ 2,288. That means the highest observed fare was about 8x higher than the lowest one.

Three airlines offer in-flight Wi-Fi on Toronto to Chicago flights:

• Air Canada
• United Airlines
• American Airlines

Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Based on prices from the last 5 days, flying between Toronto and Chicago is around C$ 298 round-trip, with a flight time of about 2h 05m. Recent bus fares are around C$ 187 round-trip, with a trip time of about 20h 20m. Compared with flying, recent bus fares are roughly 38% lower. However, taking the bus takes about 18+ hours longer each way.

One-way fares from Toronto to Chicago are currently lower than usual. Average one-way flight prices are about C$ 209, which is 32% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) – daily rates from around C$ 89:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

Near Chicago Midway Airport (MDW) – daily rates from around C$ 117:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) – daily rates from around C$ 114:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from Toronto to Chicago may depart from several airports in Toronto area, including Toronto Region of Waterloo Intl (YKF), Toronto Island (YTZ) and Toronto Pearson Intl (YYZ), with arrivals available at airports in Chicago area airports such as Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Morning flights have the fewest delays on this route, while evening departures tend to have the most.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Toronto to Chicago route, 13% of flights were delayed in the past three months, with delays averaging 2h 14m.

One-stop flights from Toronto to Chicago most commonly connect through:

• Detroit Metropolitan Wayne County (DTW) – 65% of one-stop connections
• Toronto Pearson Intl (YYZ) – 22% of one-stop connections
• Ottawa (YOW) – 4% of one-stop connections
• Montreal Pierre Elliott Trudeau Intl (YUL) – 3% of one-stop connections

Yes. Flexible dates can save you up to 11% on flights from Toronto to Chicago. Thursday is the cheapest departure day at C$ 383 round-trip on average, while Monday is the most expensive at C$ 429, a difference of C$ 46.

KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

4 airlines operate flights between Toronto and Chicago. The airlines offering direct flights on this route include:

• United Airlines
• Air Canada
• American Airlines
• Porter Airlines

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 23m, compared with 4h 35m via Toronto Pearson Intl (YYZ) and 5h 05m via Charlotte Douglas (CLT).

Chicago is 1 hour behind Toronto (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Chicago are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating Toronto to Chicago flights:

• Air Canada: offers extra legroom; offers free seat selection
• Porter Airlines: offers free seat selection
• United Airlines: offers extra legroom; offers free seat selection
• American Airlines: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• Air Canada: a carry-on bag and a checked bag in Economy Class
• Porter Airlines: a carry-on bag and a checked bag in Economy Class
• United Airlines: a carry-on bag and a checked bag in Economy Class

Baggage allowance can vary by ticket type, cabin class, route, and airline, so always check the fare details before booking.

Flights from Toronto to Chicago are quite short, usually lasting less than 2 hours, which means they occur regularly and are often non-stop. Direct flights are offered by numerous airlines including American Airlines, Porter Airlines and Air Canada.

Getting from downtown Toronto to Billy Bishop Airport is simple. Passengers can choose the free express shuttle that goes from Toronto’s city centre to the mainland ferry terminal every 15 minutes. There is then an 800-meter pedestrian tunnel or a 90-second ride on the ferry, both going directly to the airport.

While there are no airports directly inside Billy Bishop Airport, there are a number of nearby hotels like the Fairmont Royal York or the Strathcona Hotel. Both are located just minutes from Billy Bishop Airport and offer comfortable rooms and a number of amenities.

If your plane was delayed or Toronto is just one leg of your journey, Toronto Pearson International Airport offers many opportunities to pass the time. The airport is fully equipped so that you can enjoy a number of shops and kiosks, a workout at Goodlife Fitness or a treatment at the spa. More interested in art? Check out the displays throughout the airport, featuring works by local artists.

One of the quickest options is to travel on the Orange Line provided by the Chicago Transit Authority, that can take passengers from the airport to downtown Chicago in about 20 minutes, with trains leaving every 15 minutes or so throughout the day.

This airport offers an impressive number of both major rental car companies and local rental car companies that all have a location right on airport property for the convenience of passengers. All of the rental car companies operate at a multi-modal facility on the airport grounds. After any flight to this airport, passengers wishing to rent a car should follow the signage to travel on the Airport Transit System that can take you from any terminal building at the airport to the multi-modal facility in no more than about five minutes.