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Not ready to book? to track prices.Find the cheapest flights from Toronto Island Airport to Chicago
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Porter Airlines flights from Toronto Island Airport to Chicago Midway Airport
Our best Porter Airlines deals on Toronto Island Airport to Chicago Midway Airport flight tickets
Air Transat flights from Toronto Island Airport to Chicago Midway Airport
Our best Air Transat deals on Toronto Island Airport to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Toronto Island Airport 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 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 Island Airport, with most prices found around $208. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Toronto Island Airport during the month May is also very affordable. Most momondo users find prices during this month for around $241.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Toronto Island Airport. The lowest ticket price found for a Thursday departure recently was $253. 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, Tuesday is the most expensive day to depart from Toronto Island Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $292.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Toronto Island Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $249 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $284. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Toronto Island to Chicago Midway flight route?
Fly from Toronto Island to Chicago Midway for the best Toronto Island - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Toronto Island Airport when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $275 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Toronto Island Airport for as low as $224 on momondo.
What cabin class options are available on Toronto Island to Chicago Midway flights?
There are 4 cabin classes available to choose from on Toronto Island 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 many flights depart from Toronto Island Airport to Chicago Midway Airport on average per day?
1 flights are operational daily from Toronto Island Airport to Chicago Midway Airport as of February 2025. The most popular departure time for this route is 11:00AM, with 100% of flights per day taking off at noon.
How many flights depart from Toronto Island Airport to Chicago Midway Airport on average per week?
12 flights are operational weekly from Toronto Island Airport to Chicago Midway Airport as of February 2025. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.
When to book flights from Toronto Island Airport to Chicago Midway Airport
Cheap Toronto Island Airport to Chicago Midway Airport (YTZ to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto Island Airport to Chicago Midway Airport
How far is Toronto Island to Chicago Midway by plane?
A flight from Toronto Island to Chicago Midway will travel around 442.0 mi. In terms of flight time, this usually takes a little over 1h 49m.
When did momondo last update prices for flights from Toronto Island Airport to Chicago Midway Airport?
Prices for flights from Toronto Island Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Toronto Island Airport to Chicago Midway Airport?
There is 1 operator available for flights from Toronto Island Airport to Chicago Midway Airport as of February 2025.
How old do you have to be to fly from Toronto Island Airport 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 Island Airport 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 Island Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Toronto Island Airport and Chicago Midway Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 33.47% of the total bookings. Other popular models include Boeing 737 MAX 8 with 15.56%, Airbus A220-300 with 13.69%, and Embraer 175 (Enhanced Winglets) with 11.53%.
What is the most popular airline from Toronto Island Airport to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Toronto Island Airport to Chicago Midway Airport is Porter Airlines (100% of total bookings).
Best airlines flying from Toronto Island Airport to Chicago Midway Airport
Compare and see reviews for airlines that fly from Toronto Island Airport to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $209 | Free Cancellation | Rating 7.9 276 reviews |
Porter Airlines Flights From Toronto Island Airport to Chicago Midway Airport
Across 6 Porter Airlines flights from Toronto Island Airport to Chicago Midway Airport this week, the average price was $261, with the best Porter Airlines deals starting from $209 round-trip. 276 users have rated Porter Airlines on momondo, with an average score of 7.9/10.
Traveling 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?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Toronto to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Toronto to Chicago.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Toronto to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.