C$ 181 Find Cheap Flights from Toronto Island to Chicago Midway Airport – Compare and Save

Among airlines operating Toronto Island Airport to Chicago Midway Airport flights:

• Porter Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Porter Airlines operates flights between Toronto Island Airport and Chicago Midway Airport.

Flights from Toronto Island Airport to Chicago Midway Airport usually depart from Toronto Island (YTZ) and arrive at Chicago Midway (MDW).

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 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 Midway Airport:

• Economy Class
• Premium Economy Class

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 36–C$ 138 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

The De Havilland (Bombardier) DHC-8-400 Dash 8Q family is used most often on this route, operated mainly by Porter Airlines and Air Transat. Other aircraft seen on the route include Boeing 737-900 variants.

Yes. Being flexible with your travel dates can save you up to 12% on the Toronto Island Airport to Chicago Midway Airport route. Monday is the cheapest departure day at C$ 335 round-trip on average, while Sunday is the most expensive at C$ 378, a difference of C$ 43. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Toronto Island Airport to Chicago Midway Airport flights, with 50% leaving in that window. Afternoon departures account for 50%, Evening flights for 0%, and Night flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

• Earliest: departs at 10:10 am and lands at 12:00 pm
• Latest: departs at 1:45 pm and lands at 3:35 pm.

The flight takes about 1h 50m.

Last-minute fares on this route – booked within 2 weeks of departure – run 63% above the route average of C$ 358. Book 26 weeks before departure for the lowest fares.

A direct flight from Toronto Island Airport to Chicago Midway Airport takes 1h 50m, covering 1,145 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$ 286 to C$ 1,290. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from Toronto Island Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about C$ 185, which is 25% below the typical average for this route.

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

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around C$ 44 for economy cars. Top options include:
· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Round-trip flights from Toronto Island Airport to Chicago Midway Airport range from C$ 284 to C$ 478, with an average of C$ 358 over the past 12 months. Anything below C$ 284 counts as a good deal.