$145 Find Cheap Flights from Toronto Pearson Airport to Chicago Midway Airport - Compare and Save

Flights from Toronto Pearson Intl Airport to Chicago Midway Airport usually depart from Toronto Pearson Intl (YYZ) and arrive at Chicago Midway (MDW).

Only Economy Class is available on flights from Toronto Pearson Intl Airport to Chicago Midway Airport.

One-stop flights from Toronto Pearson Intl Airport 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 43% on the Toronto Pearson Intl Airport to Chicago Midway Airport route. Thursday is the cheapest departure day at $265 round-trip on average, while Monday is the most expensive at $461, a difference of $196. 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 Pearson Intl Airport 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, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

There are currently no nonstop flights available from Toronto Pearson Intl Airport to Chicago Midway Airport. Flights with 1 layover take between 3h 59m 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $230 to $1,397. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Toronto Pearson Intl Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $147, which is 38% below the typical average for this route.

Delta is the only airline operating Toronto Pearson Intl Airport 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 Pearson Intl 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 $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Toronto Pearson Intl Airport to Chicago Midway Airport range from $265 to $368, with an average of $279 over the past 12 months. Anything below $265 counts as a good deal.