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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?
In general, March is the cheapest month to fly from Toronto Island Airport to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 263. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Toronto Island Airport during the month January is also very affordable. Most momondo users find prices during this month for around C$ 288.
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$ 336. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Toronto Island Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 365.
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 Island Airport to Chicago Midway Airport during this time can be as low as C$ 349. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 575.
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 C$ 357 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 C$ 297 on momondo.
What cabin class options are available on Toronto Island to Chicago Midway flights?
There are 1 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?
3 flights are operational daily from Toronto Island Airport to Chicago Midway Airport as of April 2025. The most popular departure time for this route is 3:00p.m., with 50% of flights per day taking off at noon.
How many flights depart from Toronto Island Airport to Chicago Midway Airport on average per week?
24 flights are operational weekly from Toronto Island Airport to Chicago Midway Airport as of April 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?
Chicago Midway is 711.3 km away from Toronto Island. 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 are updated 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 April 2025.
How old do you have to be to fly from Toronto Island Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Toronto Island Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek 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?
momondo data reveals that the most frequently booked plane model on the route from Toronto Island Airport to Chicago Midway Airport is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 29.14% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.78%, Embraer 175 (Enhanced Winglets) at 13.47%, and Airbus A220-300 at 9.93%.
What is the most popular airline from Toronto Island Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Toronto Island Airport and Chicago Midway Airport, the leading airline is Porter Airlines, making up 100% of the 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 C$ 268 | Free Cancellation | Rating 8.0 280 reviews |
Porter Airlines Flights From Toronto Island Airport to Chicago Midway Airport
Porter Airlines flies from Toronto Island Airport to Chicago Midway Airport around 12 times per week, with 280 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Toronto Island Airport to Chicago Midway Airport in the last 72 hours was C$ 193 (round-trip), much lower than the average airfare cost of C$ 268 for Porter Airlines flights on this route.
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?
Finding the right flight to Chicago from Toronto is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Toronto to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Toronto to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.
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.