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Not ready to book? to track prices.Find the cheapest flights from Toronto to Chicago
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Porter Airlines flights from Toronto to Chicago Midway Airport
Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets
Air Transat flights from Toronto to Chicago Midway Airport
Our best Air Transat deals on Toronto to Chicago Midway Airport flight tickets
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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?
What is the cheapest month to fly to Chicago Midway Airport?
In general, May 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$ 282. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Toronto during the month February is also very affordable. Most momondo users find prices during this month for around C$ 291.
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 Wednesday when prices can be found for as low as C$ 324. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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$ 361.
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 in the morning. Flights from Toronto to Chicago Midway Airport during this time can be as low as C$ 330. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 567.
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 flights?
There are 1 cabin classes available to choose from on Toronto to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How have Toronto to Chicago Midway Airport flight prices changed over time?
How many flights depart from Toronto to Chicago Midway Airport on average per day?
3 flights are operational daily from Toronto to Chicago Midway Airport as of June 2025. The most popular departure time for this route is 7:00a.m., with 63% of flights per day taking off at noon.
How many flights depart from Toronto to Chicago Midway Airport on average per week?
As of June 2025, 26 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 15% 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
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 49m.
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 are 2 operators available for flights from Toronto to Chicago Midway Airport as of June 2025.
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 31.14% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 18.16%, Boeing 737-800 with 14.61%, and Airbus A220-300 with 10.21%.
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 89% of all bookings. The subsequent popular airline is Air Transat at 11%.
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$ 237 | Free Cancellation | Rating 8.0 288 reviews | |||
| PriceFrom C$ 471 | Free Cancellation | Rating 7.2 2,868 reviews |
Porter Airlines Flights From Toronto to Chicago Midway Airport
Porter Airlines flight deals from Toronto to Chicago Midway Airport start from C$ 173 round-trip. Over the 13 Porter Airlines flights for this route in a normal week, average airfare is usually C$ 267 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.