$148 Find Cheap Flights from Toronto Island to Chicago - Compare and Save

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

• Earliest: departs at 10:29 am and lands at 12:33 pm
• Latest: departs at 7:40 pm and lands at 9:44 pm.

The flight takes about 2h 04m.

Only Economy Class is available on flights from Toronto Island Airport to Chicago.

A nonstop flight from Toronto Island Airport to Chicago takes 2h 04m, covering 434 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 Island Airport to Chicago range from $215 to $354, with an average of $271 over the past 12 months. Anything below $215 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 59% above the $271 route average. Book 25 weeks before departure for the lowest fares.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $271 round-trip, compared to $361 via a layover through Montreal Pierre Elliott Trudeau Intl (YUL).

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $30–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Afternoon is the busiest departure period on Toronto Island Airport to Chicago flights, with 66% of flights leaving in that window. Morning departures account for 34%, evening flights for 0%, 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 $234 to $1,426. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Toronto Island Airport to Chicago are currently lower than usual. Average one-way flight prices are about $157, which is 13% 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 $63:

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

Near Chicago Midway Airport (MDW) — daily rates averaging $86:

• 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 Island Airport to Chicago usually depart from Toronto Island (YTZ) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Connecting flights from Toronto Island Airport to Chicago most commonly pass through:

• Ottawa (YOW) - 71% of one-stop connections
• Montreal Pierre Elliott Trudeau Intl (YUL) - 29% of one-stop connections

Yes. Flexible dates can save you up to 14% on flights from Toronto Island Airport to Chicago. Thursday is the cheapest departure day at $260 round-trip on average, while Sunday is the most expensive at $302, a difference of $42.

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

2 airlines operate flights between Toronto Island Airport and Chicago. The airlines offering nonstop flights on this route include:

• Porter Airlines
• Air Canada

Flying via Montreal Pierre Elliott Trudeau Intl (YUL) gives the shortest average 1-stop total travel time at 5h 37m, compared with 5h 38m via Ottawa (YOW).

Chicago is 1 hour behind Toronto Island 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 Island Airport to Chicago flights:

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

• Porter Airlines: a cabin bag and a checked bag in Economy Class
• Air Canada: a cabin bag and a checked bag in Economy Class
• Air Transat: 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.