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Not ready to book? to track prices.Porter Airlines flights from Toronto to Chicago Midway Airport
Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets
Delta flights from Toronto to Chicago Midway Airport
Our best Delta deals on Toronto to Chicago Midway Airport flight tickets
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Use the filters below to find and compare flights from Toronto to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 12/10
6:00 am-9:37 am
1 stop4h 37m
Chicago Midway
Tue 12/15
9:37 am-5:20 pm
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Mon 12/7
2:25 pm-6:01 pm
1 stop4h 36m
Chicago Midway
Thu 12/10
9:37 am-5:20 pm
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Fri 12/4
2:25 pm-6:01 pm
1 stop4h 36m
Chicago Midway
Wed 12/9
9:37 am-5:20 pm
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 12/8
2:25 pm-6:01 pm
1 stop4h 36m
Chicago Midway
Fri 12/11
6:41 pm-11:07 pm
1 stop3h 26m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 12/10
6:00 am-9:37 am
1 stop4h 37m
Chicago Midway
Sun 12/13
6:41 pm-11:07 pm
1 stop3h 26m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 12/5
6:00 am-1:01 pm
1 stop8h 01m
Chicago Midway
Mon 12/14
6:41 pm-11:07 pm
1 stop3h 26m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Fri 12/4
2:25 pm-6:01 pm
1 stop4h 36m
Chicago Midway
Thu 12/10
9:37 am-5:20 pm
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 12/8
9:45 am-1:01 pm
1 stop4h 16m
Chicago Midway
Thu 12/10
9:37 am-5:20 pm
1 stop6h 43m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 10/20
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Wed 10/21
11:45 am-2:25 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Wed 10/21
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Sat 10/24
11:45 am-2:25 pm
Nonstop1h 40m
See travel insights to Chicago from
How to get the cheapest flight ticket from Toronto to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Toronto and Chicago Midway Airport?
Prices are currently low for flights on this route.
Typical prices usually range from $413 to $471.The lowest price recently found on this route was $285.
What is the cheapest month to fly to Chicago Midway Airport?
The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto, with most prices found around $204. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Toronto during the month December is also very affordable. Most momondo users find prices during this month for around $211.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Toronto. The lowest ticket price found for a Tuesday departure recently was $229. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $347.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Toronto in the morning is the least expensive time of day to depart. momondo users have found prices as low as $290 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $291. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Toronto to Chicago Midway flight route?
Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago Midway flight prices
What cabin class options are available on Toronto to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on Toronto to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Toronto to Chicago Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Toronto to Chicago Midway Airport.
How often are flights from Toronto to Chicago delayed?
Historically, on average around 16% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 107 minutes.
What is the most punctual flight time for Toronto to Chicago flights?
Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.
What day of the week experiences the fewest flight delays on this route?
Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.
Which airline has the best punctuality record on Toronto to Chicago flights?
According to our data, Porter Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.
How many flights depart from Toronto to Chicago Midway Airport on average per day?
As of October 2026, there are 4 flights per day flying from Toronto to Chicago Midway Airport. The most common time of day flights depart is 10:00AM, with 50% of flights taking off at noon.
How many flights depart from Toronto to Chicago Midway Airport on average per week?
As of October 2026, there are 28 flights per week flying from Toronto to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
When to book flights from Toronto to Chicago Midway Airport
Cheap Toronto to Chicago Midway Airport (YTO to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago Midway Airport
Frequently asked questions about flying from Toronto to Chicago Midway Airport
How far is Toronto to Chicago Midway by plane?
There are 443.1 mi between Toronto and Chicago Midway. Typically, this will take 1h 50m by plane in normal conditions.
When did momondo last update prices for flights from Toronto to Chicago Midway Airport?
Prices for flights from Toronto to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Toronto to Chicago Midway Airport?
As of October 2026, there is 1 operator available to choose from for flights from Toronto to Chicago Midway Airport.
How old do you have to be to fly from Toronto to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Toronto to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Toronto to Chicago Midway Airport is De Havilland (Bombardier) DHC-8-400 Dash 8Q (42.48% of total bookings). The next most popular plane models are Boeing 737-900 (9.77%), Embraer 175 (Enhanced Winglets) (8.52%), and Boeing 737-800 (6.34%).
What is the most popular airline from Toronto to Chicago Midway Airport?
Based on momondo bookings for flights between Toronto and Chicago Midway Airport, the leading airline is Porter Airlines, making up 100% of the total bookings.
Best airlines flying from Toronto to Chicago Midway Airport
Compare and see reviews for airlines that fly from Toronto to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $185 | Free Cancellation | Rating 8.0 468 reviews |
Porter Airlines Flights From Toronto to Chicago Midway Airport
Porter Airlines is one of the most popular airlines flying from Toronto to Chicago Midway Airport, operating 14 flights/week on average for this route. A good Porter Airlines flight deal for Toronto to Chicago Midway Airport starts from $185 round-trip, up to an average price of $365. Our users have rated Porter Airlines at 8.0/10.
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Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Toronto to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Toronto to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Toronto which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Toronto to Chicago?
Once all potential Toronto to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.