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

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.

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

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).

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.

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

• Economy Class
• Premium Economy Class
• First Class

On this route, direct flights are cheaper than layover options on average. Direct fares average C$ 360 round-trip, compared to C$ 482 via a layover through Detroit Metropolitan Wayne County (DTW).

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 36–C$ 139 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

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

• Detroit Metropolitan Wayne County (DTW) – 92% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) – 5% of one-stop connections
• Orlando (MCO) – 3% of one-stop connections

Detroit Metropolitan Wayne County (DTW) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 11% on the Toronto to Chicago Midway Airport route. Monday is the cheapest departure day at C$ 347 round-trip on average, while Tuesday is the most expensive at C$ 387, a difference of C$ 40. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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, 86% of flights were delayed in the past 3 months, with delays averaging 1 hour 57 minutes.

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 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 62% above the route average of C$ 362. Book 26 weeks before departure for the lowest fares.

A direct flight from Toronto to Chicago Midway Airport takes 1h 50m, covering 1,148 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$ 284 to C$ 1,923. That means the highest observed fare was about 7x 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$ 183, which is 26% below the typical average for this route.

Delta is the only airline operating Toronto to Chicago Midway Airport flights. 14% of its flights are on time.

Afternoon flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 59m, compared with 6h 14m 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.

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

Round-trip flights from Toronto to Chicago Midway Airport range from C$ 287 to C$ 482, with an average of C$ 362 over the past 12 months. Anything below C$ 287 counts as a good deal.