C$ 182 Find Cheap Flights from Toronto to Chicago – Compare and Save

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.

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.

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

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).

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

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

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

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

Prices vary by airline.

On this route, layover flights are cheaper than direct options on average. Layover fares average C$ 281 round-trip via Charlotte Douglas (CLT), compared to C$ 388 for direct.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 34–C$ 139 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

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

• Detroit Metropolitan Wayne County (DTW) – 67% of one-stop connections
• Toronto Pearson Intl (YYZ) – 17% of one-stop connections
• Minneapolis St Paul (MSP) – 3% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) – 2% of one-stop connections

Detroit Metropolitan Wayne County (DTW) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 7% on the Toronto to Chicago route. Thursday is the cheapest departure day at C$ 380 round-trip on average, while Monday is the most expensive at C$ 406, a difference of C$ 26. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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 3 months, with delays averaging 2 hours 15 minutes.

Afternoon is the busiest departure period on Toronto to Chicago flights, with 42% leaving in that window. Morning departures account for 37%, Evening flights for 21%, and Night flights for 0%.

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.

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

• Earliest: departs at 6:30 am and lands at 8:37 am
• Latest: departs at 9:00 pm and lands at 11:07 pm.

The flight takes about 2h 07m.

Last-minute fares on this route – booked within 2 weeks of departure – run 63% above the route average of C$ 389. Book 26 weeks before departure for the lowest fares.

A direct flight from Toronto to Chicago takes 2h 07m, 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 275 to C$ 2,143. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Toronto to Chicago are currently lower than usual. Average one-way flight prices are about C$ 190, which is 38% below the typical average for this route.

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.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Based on prices from the last 5 days, flying between Toronto and Chicago is around C$ 275 round-trip, with a flight time of about 1h 58m. Recent bus fares are around C$ 203 round-trip, with a trip time of about 14h 25m. Compared with flying, recent bus fares are roughly 27% lower. However, taking the bus takes about 12+ hours longer each way.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 33m, compared with 4h 35m via Toronto Pearson Intl (YYZ) and 4h 49m via Minneapolis St Paul (MSP).

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

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$ 24:

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

Near Chicago Midway Airport (MDW) – daily rates from around C$ 45:

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

Near Chicago Greater Rockford Airport (RFD) – daily rates from around C$ 42:

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

Round-trip flights from Toronto to Chicago range from C$ 309 to C$ 512, with an average of C$ 389 over the past 12 months. Anything below C$ 309 counts as a good deal.

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

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