C$ 218 Find Cheap Flights from Toronto to Chicago Midway Airport – Compare and Save

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

• Economy Class
• Premium Economy Class
• First Class

There are currently no direct flights available from Toronto to Chicago Midway Airport. Flights with 1 layover take between 4h 04m and 24h 55m in total, depending on the connection.

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 to Chicago Midway Airport range from C$ 293 to C$ 503, with an average of C$ 372 over the past 12 months. Anything below C$ 293 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 58% above the C$ 372 route average. Book 26 weeks before departure for the lowest fares.

On this route, direct flights are cheaper than layover options on average. Direct fares average C$ 371 round-trip, compared to C$ 431 via a layover through Atlanta Hartsfield-Jackson (ATL).

Delta is the only airline operating Toronto to Chicago Midway Airport flights. 25% of its flights are on time.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 41–C$ 140 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 354 to C$ 2,754. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Toronto to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about C$ 221, which is 14% below the typical average for this route.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around C$ 45 for economy cars. Top options include:

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

Flights from Toronto to Chicago Midway Airport may depart from several airports in Toronto area, including Toronto Region of Waterloo Intl (YKF), Toronto Island (YTZ) and Toronto Pearson Intl (YYZ). Flights usually arrive at Chicago Midway (MDW).

Afternoon flights have the fewest delays on this route.

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 to Chicago Midway Airport route, 75% of flights were delayed in the past three months, with delays averaging 1h 57m.

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

• Detroit Metropolitan Wayne County (DTW) – 95% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) – 2% of one-stop connections
• Orlando (MCO) – 2% of one-stop connections

Yes. Flexible dates can save you up to 15% on flights from Toronto to Chicago Midway Airport. Tuesday is the cheapest departure day at C$ 340 round-trip on average, while Friday is the most expensive at C$ 396, a difference of C$ 56.

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

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 04m, compared with 5h 11m via Atlanta Hartsfield-Jackson (ATL) and 24h 55m via Orlando (MCO).

Chicago Midway Airport is 1 hour behind Toronto (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 Midway Airport are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Among airlines operating Toronto to Chicago Midway Airport flights:

• 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:

• 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

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