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CA $212 Cheap Flights from Toronto (YYZ) to Chicago (MDW)

View CA $212 flight on Tue, Sep 1, 2026Opens in a new window

Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at CA $212 for one-way flights and CA $342 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Sep 26 - Tue, Sep 29
YYZ
Toronto
MDW
Chicago
CA $342 Roundtrip, just found
CA $342
Roundtrip
just found
Select Delta flight, departing Sat, Sep 26 from Toronto to Chicago, returning Tue, Sep 29, priced at CA $342 just found
Delta
Sat, Sep 26 - Tue, Sep 29
YYZ
Toronto
MDW
Chicago
CA $369 Roundtrip, just found
CA $369
Roundtrip
just found
Select Delta flight, departing Sat, Sep 26 from Toronto to Chicago, returning Tue, Sep 29, priced at CA $369 just found
Delta
Fri, Sep 11 - Sun, Sep 13
YYZ
Toronto
MDW
Chicago
CA $370 Roundtrip, just found
CA $370
Roundtrip
just found
Select Delta flight, departing Fri, Sep 11 from Toronto to Chicago, returning Sun, Sep 13, priced at CA $370 just found
Delta
Sat, Aug 29 - Mon, Sep 14
YYZ
Toronto
MDW
Chicago
CA $375 Roundtrip, found 22 hours ago
CA $375
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Aug 29 from Toronto to Chicago, returning Mon, Sep 14, priced at CA $375 found 22 hours ago
Delta
Wed, Sep 30 - Sat, Oct 3
YYZ
Toronto
MDW
Chicago
CA $378 Roundtrip, just found
CA $378
Roundtrip
just found
Select Delta flight, departing Wed, Sep 30 from Toronto to Chicago, returning Sat, Oct 3, priced at CA $378 just found
Delta
Sun, Nov 15 - Thu, Nov 19
YYZ
Toronto
MDW
Chicago
CA $388 Roundtrip, found 3 days ago
CA $388
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Nov 15 from Toronto to Chicago, returning Thu, Nov 19, priced at CA $388 found 3 days ago
Delta
Sat, Sep 26 - Fri, Oct 2
YYZ
Toronto
MDW
Chicago
CA $394 Roundtrip, just found
CA $394
Roundtrip
just found
Select Delta flight, departing Sat, Sep 26 from Toronto to Chicago, returning Fri, Oct 2, priced at CA $394 just found
Delta
Sat, Sep 26 - Sat, Oct 3
YYZ
Toronto
MDW
Chicago
CA $405 Roundtrip, found 1 hour ago
CA $405
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Sep 26 from Toronto to Chicago, returning Sat, Oct 3, priced at CA $405 found 1 hour ago
Delta
Fri, Sep 11 - Sun, Sep 13
YYZ
Toronto
MDW
Chicago
CA $406 Roundtrip, just found
CA $406
Roundtrip
just found
Select Delta flight, departing Fri, Sep 11 from Toronto to Chicago, returning Sun, Sep 13, priced at CA $406 just found
Delta
Fri, Aug 28 - Sat, Aug 29
YYZ
Toronto
MDW
Chicago
CA $407 Roundtrip, found 1 hour ago
CA $407
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Aug 28 from Toronto to Chicago, returning Sat, Aug 29, priced at CA $407 found 1 hour ago

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 $447
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $447

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

January is typically the cheapest month to fly

From CA $301 - CA $849 per traveller.

Frequently asked questions

How much does a flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from CA $212 and cheap return flights from CA $342 YYZ to MDW with Expedia. One-way flights typically cost between CA$278 and CA$1756, and return flights often range between CA$456 and CA$3458. 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 YYZ to MDW ticket fares go up or down.
What is the cheapest month to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YYZ 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 (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter YYZ to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
Delta is one of the cheapest airlines offering connecting return flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$308 for flights that can be booked for departure within the next year. 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 (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Toronto, ON (YYZ-Pearson Intl.) 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 time to fly from Toronto, ON (YYZ-Pearson Intl.) 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 (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 20 connecting flights per day from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW). Some common connection points include Detroit Metropolitan Wayne County (DTW), Liberty International (EWR), and Hartsfield-Jackson Atlanta International (ATL).
What is the earliest flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) typically departs around 6:00 AM. This service is offered by Delta. This is a seasonal service, active in September and October. 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 (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) on a Thursday, with around 31 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Delta, Air Canada, and United.
What are the most popular departure times for flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) are in the early morning, from 6am to 9am. Many major carriers, including Delta, Air Canada and United, offer flights during this window. Many travellers prefer this time as it allows you to arrive in Chicago early, giving you a full day for business or exploring.
How long does it take to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.). For flights with one stop, you can expect the journey to take around 7 hours 30 minutes. If you opt for flights with two or more stops, the travel time increases significantly to about 15 hours. The distance between these two airports is approximately 697 kilometers. Keep in mind that actual flight times can vary due to factors like layover duration, routing, and weather conditions.
Can you fly business or first class from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly first class between YYZ and MDW. First class cabins are available on Delta.
How do I earn miles on a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Toronto, ON (YYZ-Pearson Intl.) 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 (YYZ)?
If you're planning to travel to Chicago from Pearson Intl. (YYZ), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Liberty Intl. (EWR), Nashville Intl. (BNA), or Washington Dulles Intl. (IAD) 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 (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Toronto, ON (YYZ-Pearson Intl.) 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 (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Toronto, ON (YYZ-Pearson Intl.) 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 (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Toronto, ON (YYZ-Pearson Intl.) 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

Origin airport
Pearson Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
CA $333
Distance
692 km

Book with confidence

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 Pearson Intl., YYZ 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 $342 rising to CA $407.  

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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