$139 Find Cheap Flights from Toronto Pearson Airport to Chicago - Compare and Save

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

• Earliest: departs at 6:45 am and lands at 8:59 am
• Latest: departs at 7:26 pm and lands at 9:40 pm.

The flight takes about 2h 14m.

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

• Economy Class
• Business Class
• First Class

A nonstop flight from Toronto Pearson Intl Airport to Chicago takes 2h 14m, covering 424 miles.

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 Pearson Intl Airport to Chicago range from $236 to $374, with an average of $288 over the past 12 months. Anything below $236 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 64% above the $288 route average. Book 13 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $203 round-trip via Charlotte Douglas (CLT), compared to $288 for nonstop.

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

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

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$100 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 Pearson Intl Airport to Chicago flights, with 41% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 26%, 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 $222 to $1,597. That means the highest observed fare was about 7x higher than the lowest one.

Three airlines offer in-flight Wi-Fi on Toronto Pearson Intl Airport 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.

One-way fares from Toronto Pearson Intl Airport to Chicago are currently lower than usual. Average one-way flight prices are about $164, which is 30% 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 averaging $64:

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

Near Chicago Midway Airport (MDW) — daily rates averaging $84:

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

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

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

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).

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 Pearson Intl Airport to Chicago route, 13% of flights were delayed in the past 3 months, with delays averaging 2h 14m.

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

• Detroit Metropolitan Wayne County (DTW) - 91% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 2% of one-stop connections
• Charlotte Douglas (CLT) - 1% of one-stop connections
• Washington, D.C. Reagan-National (DCA) - 1% of one-stop connections

Yes. Flexible dates can save you up to 13% on flights from Toronto Pearson Intl Airport to Chicago. Thursday is the cheapest departure day at $280 round-trip on average, while Monday is the most expensive at $319, a difference of $39.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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

• United Airlines
• American Airlines
• Air Canada

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 23m, compared with 5h 05m via Charlotte Douglas (CLT) and 5h 07m via Washington, D.C. Reagan-National (DCA).

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.

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

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
• Porter Airlines: 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 cabin bag and a checked bag in Economy Class
• United Airlines: a cabin bag and a checked bag in Economy Class
• American Airlines: a cabin bag and a checked bag in Economy Class

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