C$ 183 Find Cheap Flights from Toronto Pearson Airport to Chicago – Compare and Save

Among airlines operating Toronto Pearson Intl Airport to Chicago flights:

• Air Canada: offers extra legroom; 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.

3 airlines operate flights between Toronto Pearson Intl Airport and Chicago. The airlines offering direct flights on this route include:

• United Airlines
• American Airlines
• Air Canada

Flights from Toronto Pearson Intl Airport to Chicago usually depart from Toronto Pearson Intl (YYZ) and may arrive at several airports in Chicago area, including 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
• United Airlines: a carry-on bag and a checked bag in Economy Class
• American 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.

Three cabin classes are available on flights from Toronto Pearson Intl Airport to Chicago:

• Economy Class
• Business Class
• First Class

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$ 399 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 Pearson Intl Airport to Chicago most commonly connect through:

• Detroit Metropolitan Wayne County (DTW) – 83% of one-stop connections
• Minneapolis St Paul (MSP) – 4% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) – 3% of one-stop connections
• Fort Lauderdale (FLL) – 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 11% on the Toronto Pearson Intl Airport to Chicago route. Thursday is the cheapest departure day at C$ 387 round-trip on average, while Monday is the most expensive at C$ 433, a difference of C$ 46. 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 Pearson Intl Airport to Chicago route, 13% of flights were delayed in the past 3 months, with delays averaging 2 hours 15 minutes.

Morning is the busiest departure period on Toronto Pearson Intl Airport to Chicago flights, with 40% leaving in that window. Afternoon departures account for 40%, Evening flights for 20%, 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 Pearson Intl Airport 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 66% above the route average of C$ 400. Book 13 weeks before departure for the lowest fares.

A direct flight from Toronto Pearson Intl Airport to Chicago takes 2h 07m, covering 1,099 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 Pearson Intl Airport to Chicago are currently lower than usual. Average one-way flight prices are about C$ 204, 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 Pearson Intl Airport 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.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 33m, compared with 4h 49m via Minneapolis St Paul (MSP) and 5h 05m via Charlotte Douglas (CLT).

Chicago is 1 hour behind Toronto Pearson Intl Airport (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 Pearson Intl Airport to Chicago range from C$ 325 to C$ 518, with an average of C$ 400 over the past 12 months. Anything below C$ 325 counts as a good deal.

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

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