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

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.

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

• Porter Airlines
• Air Canada

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).

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

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

Two cabin classes are available on flights from Toronto Island Airport to Chicago:

• Economy Class
• Premium Economy Class

On this route, direct flights are cheaper than layover options on average. Direct fares average C$ 367 round-trip, compared to C$ 506 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 C$ 35–C$ 140 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

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

• Montreal Pierre Elliott Trudeau Intl (YUL) – 67% of one-stop connections
• Ottawa (YOW) – 33% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

Yes. Being flexible with your travel dates can save you up to 13% on the Toronto Island Airport to Chicago route. Monday is the cheapest departure day at C$ 354 round-trip on average, while Sunday is the most expensive at C$ 404, a difference of C$ 50. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Afternoon is the busiest departure period on Toronto Island Airport to Chicago flights, with 66% leaving in that window. Morning departures account for 34%, Evening flights for 0%, 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 Island Airport to Chicago:

• Earliest: departs at 10:10 am and lands at 12:14 pm
• Latest: departs at 7:40 pm and lands at 9:44 pm.

The flight takes about 2h 04m.

Last-minute fares on this route – booked within 2 weeks of departure – run 61% above the route average of C$ 367. Book 26 weeks before departure for the lowest fares.

A direct flight from Toronto Island Airport to Chicago takes 2h 04m, covering 1,125 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$ 287 to C$ 2,045. That means the highest observed fare was about 7x 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 C$ 186, which is 24% below the typical average for this route.

Flying via Montreal Pierre Elliott Trudeau Intl (YUL) gives the shortest average 1-stop total travel time at 5h 37m, compared with 5h 42m 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.

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$ 43:

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

Round-trip flights from Toronto Island Airport to Chicago range from C$ 292 to C$ 482, with an average of C$ 367 over the past 12 months. Anything below C$ 292 counts as a good deal.