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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
Fri 4/12
2:25 p.m.-6:01 p.m.
1 stop4h 36m
Chicago Midway
Thu 10/12
9:37 a.m.-5:20 p.m.
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 10/12
6:00 a.m.-9:37 a.m.
1 stop4h 37m
Chicago Midway
Tue 15/12
9:37 a.m.-5:20 p.m.
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Mon 7/12
2:25 p.m.-6:01 p.m.
1 stop4h 36m
Chicago Midway
Thu 10/12
9:37 a.m.-5:20 p.m.
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 8/12
9:45 a.m.-1:01 p.m.
1 stop4h 16m
Chicago Midway
Thu 10/12
9:37 a.m.-5:20 p.m.
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Fri 4/12
2:25 p.m.-6:01 p.m.
1 stop4h 36m
Chicago Midway
Wed 9/12
9:37 a.m.-5:20 p.m.
1 stop6h 43m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 8/12
2:25 p.m.-6:01 p.m.
1 stop4h 36m
Chicago Midway
Fri 11/12
6:41 p.m.-11:07 p.m.
1 stop3h 26m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 10/12
6:00 a.m.-9:37 a.m.
1 stop4h 37m
Chicago Midway
Sun 13/12
6:41 p.m.-11:07 p.m.
1 stop3h 26m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 5/12
6:00 a.m.-1:01 p.m.
1 stop8h 01m
Chicago Midway
Mon 14/12
6:41 p.m.-11:07 p.m.
1 stop3h 26m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Fri 12/3
9:30 a.m.-10:20 a.m.
Nonstop1h 50m
Chicago Midway
Sun 14/3
5:35 p.m.-8:17 p.m.
Nonstop1h 42m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 20/10
1:45 p.m.-2:35 p.m.
Nonstop1h 50m
Chicago Midway
Fri 23/10
3:20 p.m.-6:00 p.m.
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 C$ 588 to C$ 671.The lowest price recently found on this route was C$ 406.
What is the cheapest month to fly to Chicago Midway Airport?
In general, January is the cheapest month to fly from Toronto to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 291. 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 C$ 300.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
The cheapest day to depart on your flight to Chicago Midway Airport is on a Thursday when prices can be found for as low as C$ 331. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 391.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Our most recent data shows that the best time of day to fly to Chicago Midway Airport is at noon. Flights from Toronto to Chicago Midway Airport during this time can be as low as C$ 341. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 690.
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 departing 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 that experiences the fewest 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 has had the least 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?
4 flights are operational daily from Toronto to Chicago Midway Airport as of October 2026. The most popular departure time for this route is 10:00a.m., with 50% of flights per day taking off at noon.
How many flights depart from Toronto to Chicago Midway Airport on average per week?
As of October 2026, 28 flights take off from Toronto and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly 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 713.1 km between Toronto and Chicago Midway. By plane, this route typically takes 1h 50m.
When did momondo last update prices for flights from Toronto to Chicago Midway Airport?
Prices for flights from Toronto to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Toronto to Chicago Midway Airport?
There is 1 operator available for flights from Toronto to Chicago Midway Airport as of October 2026.
How old do you have to be to fly from Toronto to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Toronto to Chicago Midway Airport?
Based on momondo bookings for flights between Toronto and Chicago Midway Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 42.48% of the total bookings. Other popular models include Boeing 737-900 with 9.77%, Embraer 175 (Enhanced Winglets) with 8.52%, and Boeing 737-800 with 6.34%.
What is the most popular airline from Toronto to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Toronto to Chicago Midway Airport is Porter Airlines, representing 100% of all 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 C$ 254 | Free Cancellation | Rating 8.0 468 reviews |
Porter Airlines Flights From Toronto to Chicago Midway Airport
Porter Airlines flight deals from Toronto to Chicago Midway Airport start from C$ 254 round-trip. Over the 14 Porter Airlines flights for this route in a normal week, average airfare is usually C$ 346 round-trip - but some users have found much cheaper deals with momondo.
Travelling to a place near Chicago?
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?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Toronto to Chicago for you.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Toronto with this policy.
How can momondo help me find flights from Toronto to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.