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CA $192 Cheap Flights from Toronto (YTZ) to Chicago (MDW)

View CA $192 flight on Thu, Sep 24, 2026Opens in a new window

Popular airlines from Billy Bishop Toronto City Airport (YTZ) to Chicago Midway Airport (MDW)

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Cheap flights from Toronto (YTZ) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $192 for one-way flights and CA $322 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Sep 24 - Mon, Sep 28
YTZ
Toronto
MDW
Chicago
CA $322 Roundtrip, just found
CA $322
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Sep 24 from Toronto to Chicago, returning Mon, Sep 28, priced at CA $322 just found
Porter Airlines
Tue, Sep 1 - Wed, Sep 9
YTZ
Toronto
MDW
Chicago
CA $337 Roundtrip, found 3 days ago
CA $337
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Tue, Sep 1 from Toronto to Chicago, returning Wed, Sep 9, priced at CA $337 found 3 days ago
Porter Airlines
Sun, Sep 6 - Thu, Sep 10
YTZ
Toronto
MDW
Chicago
CA $344 Roundtrip, just found
CA $344
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Sep 6 from Toronto to Chicago, returning Thu, Sep 10, priced at CA $344 just found
Air Transat
Thu, Sep 24 - Mon, Sep 28
YTZ
Toronto
MDW
Chicago
CA $353 Roundtrip, just found
CA $353
Roundtrip
just found
Select Air Transat flight, departing Thu, Sep 24 from Toronto to Chicago, returning Mon, Sep 28, priced at CA $353 just found
Porter Airlines
Mon, Aug 31 - Wed, Sep 2
YTZ
Toronto
MDW
Chicago
CA $354 Roundtrip, just found
CA $354
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Aug 31 from Toronto to Chicago, returning Wed, Sep 2, priced at CA $354 just found
Porter Airlines
Thu, Sep 24 - Mon, Sep 28
YTZ
Toronto
MDW
Chicago
CA $362 Roundtrip, just found
CA $362
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Sep 24 from Toronto to Chicago, returning Mon, Sep 28, priced at CA $362 just found
Porter Airlines
Mon, Sep 7 - Thu, Sep 10
YTZ
Toronto
MDW
Chicago
CA $365 Roundtrip, just found
CA $365
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Sep 7 from Toronto to Chicago, returning Thu, Sep 10, priced at CA $365 just found
Air Transat
Thu, Sep 24 - Mon, Sep 28
YTZ
Toronto
MDW
Chicago
CA $365 Roundtrip, just found
CA $365
Roundtrip
just found
Select Air Transat flight, departing Thu, Sep 24 from Toronto to Chicago, returning Mon, Sep 28, priced at CA $365 just found
Air Transat
Sun, Sep 6 - Thu, Sep 10
YTZ
Toronto
MDW
Chicago
CA $375 Roundtrip, just found
CA $375
Roundtrip
just found
Select Air Transat flight, departing Sun, Sep 6 from Toronto to Chicago, returning Thu, Sep 10, priced at CA $375 just found
Porter Airlines
Thu, Aug 27 - Tue, Sep 1
YTZ
Toronto
MDW
Chicago
CA $376 Roundtrip, just found
CA $376
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Aug 27 from Toronto to Chicago, returning Tue, Sep 1, priced at CA $376 just found

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $441
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $441

Find the cheapest month to fly from Toronto (YTZ) to Chicago (MDW)

February is typically the cheapest month to fly

From CA $210 - CA $366 per traveller.

Frequently asked questions

How much does a flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from CA $192 and cheap return flights from CA $322 YTZ to MDW with Expedia. One-way flights typically cost between CA$222 and CA$643, and return flights often range between CA$347 and CA$1141. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when YTZ to MDW ticket fares go up or down.
What is the cheapest month to fly from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YTZ to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
There are 2 airlines offering direct flights from Billy Bishop Toronto City (YTZ) to Midway Intl. (MDW):
  • Porter Airlines operates 7 direct flights from Billy Bishop Toronto City (YTZ) to Midway Intl. (MDW) every week.
  • Air Transat operates 7 direct flights from Billy Bishop Toronto City (YTZ) to Midway Intl. (MDW) every week.
What is the cheapest airline that flies from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
Porter Airlines is one of the cheapest airlines offering nonstop return flights from Billy Bishop Toronto City (YTZ) to Midway Intl. (MDW), with tickets starting from around CA$376 for flights that can be booked for departure within the next year. Porter Airlines also offers one of the cheapest connecting return flights from Billy Bishop Toronto City (YTZ) to Midway Intl. (MDW) starting from around CA$2092. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Porter Airlines offers early morning flights. If price is the most important factor, Porter Airlines typically offers the lowest fares. Porter Airlines offers the most daily flights from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
You'll find around 1 nonstop flight per day from Billy Bishop Toronto City (YTZ) to Midway Intl. (MDW). For even more choices, look at flights that include layovers, as there is approximately 1 connecting flight per day.
What is the earliest flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) typically departs around 7:15 AM local time. This service is offered by Air Canada and Delta. This is a seasonal service, active in July and September. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Billy Bishop Toronto City (YTZ) to Chicago Midway Intl. (MDW) on a Friday, with around 4 flights available. This gives you a good selection for your travel plans. Major airlines on this route include Porter Airlines, Passaredo Transportes Aereos, and Air Canada. Flight options are notably more frequent on Fridays compared to other days of the week, offering you more flexibility.
What are the most popular departure times for flights from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Billy Bishop Toronto City (YTZ) to Midway Intl. (MDW) are in the morning, from 9am to 12pm. Many major carriers, including Porter Airlines, Passaredo Transportes Aereos and Air Canada, offer flights during this window. Many travellers prefer this time as it allows for an early start to their journey, getting them to their destination with plenty of time left in the day.
How long does it take to fly from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
A non-stop flight from Billy Bishop Toronto City (YTZ) to Chicago Midway International Airport (MDW) typically takes around 1 hour 45 minutes. This route covers a distance of approximately 711 kilometres. If you opt for a flight with two or more stops, your travel time will be significantly longer, averaging around 12 hours 20 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic.
Can you fly business or first class from Toronto, ON (YTZ) to Chicago, IL (MDW)?
Select the "Business class" and "First class" filters when looking for Toronto, ON (YTZ) to Chicago, IL (MDW) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (MDW) from Toronto, ON (YTZ)?
If you're planning to travel to Chicago from Billy Bishop Toronto City (YTZ), you typically fly into Midway Intl. (MDW). Some flights may connect through major hubs like Logan Intl. (BOS) or LaGuardia (LGA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Billy Bishop Toronto City
Destination airport
Midway Intl.
Airlines serving
Air Transat, Porter Airlines
Roundtrip price
CA $321
Distance
707 km

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Toronto to Chicago Flights

The easy way to book your flights from Toronto to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Toronto whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Toronto to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Billy Bishop Toronto City, YTZ to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Toronto to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Toronto currently is just CA $322 rising to CA $376.  

Here are more money-saving tips: 

  • Fly in September when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Toronto 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Toronto to Chicago Flights

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