$129 Cheap Flights from Toronto (YYZ) to Chicago (MDW)

View $129 flight on Fri, Jan 23, 2026Opens in a new window

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

Cheap Flights from Toronto to Chicago (YYZ-MDW)

Prices were available within the past 7 days and start at $129 for one-way flights and $201 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Nov 19 - Wed, Nov 26
YYZ
Toronto
MDW
Chicago
$201 Roundtrip, found 2 days ago
$201
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 19 from Toronto to Chicago, returning Wed, Nov 26, priced at $201 found 2 days ago
Delta
Fri, Jan 23 - Mon, Feb 2
YYZ
Toronto
MDW
Chicago
$202 Roundtrip, found 1 hour ago
$202
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Jan 23 from Toronto to Chicago, returning Mon, Feb 2, priced at $202 found 1 hour ago
Delta
Wed, Dec 3 - Mon, Dec 8
YYZ
Toronto
MDW
Chicago
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Dec 3 from Toronto to Chicago, returning Mon, Dec 8, priced at $214 found 2 days ago
Delta
Sat, Nov 15 - Mon, Nov 24
YYZ
Toronto
MDW
Chicago
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Delta flight, departing Sat, Nov 15 from Toronto to Chicago, returning Mon, Nov 24, priced at $228 just found
Delta
Wed, Dec 3 - Mon, Dec 8
YYZ
Toronto
MDW
Chicago
$254 Roundtrip, found 2 days ago
$254
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Dec 3 from Toronto to Chicago, returning Mon, Dec 8, priced at $254 found 2 days ago
Delta
Wed, Nov 26 - Sat, Nov 29
YYZ
Toronto
MDW
Chicago
$255 Roundtrip, found 20 hours ago
$255
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Nov 26 from Toronto to Chicago, returning Sat, Nov 29, priced at $255 found 20 hours ago
Delta
Wed, Nov 19 - Wed, Nov 26
YYZ
Toronto
MDW
Chicago
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 19 from Toronto to Chicago, returning Wed, Nov 26, priced at $257 found 2 days ago
Delta
Fri, Dec 5 - Wed, Dec 10
YYZ
Toronto
MDW
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Dec 5 from Toronto to Chicago, returning Wed, Dec 10, priced at $257 found 1 day ago
Delta
Wed, Nov 26 - Sat, Nov 29
YYZ
Toronto
MDW
Chicago
$258 Roundtrip, found 20 hours ago
$258
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Nov 26 from Toronto to Chicago, returning Sat, Nov 29, priced at $258 found 20 hours ago
WestJet
Mon, Nov 24 - Sat, Nov 29
YYZ
Toronto
MDW
Chicago
$262 Roundtrip, found 9 hours ago
$262
Roundtrip
found 9 hours ago
Select WestJet flight, departing Mon, Nov 24 from Toronto to Chicago, returning Sat, Nov 29, priced at $262 found 9 hours ago

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

September is typically the cheapest month to fly

From $210 - $429 per traveler.

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 center is 23 minutes. Flights from $333
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $333

Frequently asked questions

How much does a flight from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $129 or cheap return flight from $201 from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
November is the cheapest month to fly from YYZ to MDW. Planning your trip for the off-season is often the key to finding better deals on flights.
Which airlines fly direct from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
Although Toronto, ON (YYZ-Pearson Intl.) doesn't have any direct flights to Midway Intl. Airport (MDW), other airports have nonstop options. Departing from Billy Bishop Toronto City Airport (YTZ) will get you to Chicago without any layovers.
What is the cheapest airline that flies from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll fly you from YYZ to MDW. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
Nonstop flights from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from YYZ to MDW?
Generally you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* However, this can change based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
Select a flight from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Pearson Intl. Airport (YYZ)?
Explore your flight options from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can touch down at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from YYZ to MDW just before your trip is usually more expensive. But if you're flexible with your departure dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a YYZ to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a YYZ to MDW flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one convenient place takes the hassle out of travel planning. Just pick your flights and choose from our extensive range of stays, then tailor your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
Generally, it's possible to cancel or reschedule your YYZ to MDW flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Pearson Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$200
Distance
432 mi

Book with confidence

Toronto to Chicago Flights

The cheapest times to fly from Toronto to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Toronto to Chicago are during the month of November. You can find some of the cheapest flights from Toronto to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Toronto to Chicago

Sunday is one of the best days to book for cheap flights from Toronto to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Toronto to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Toronto to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $129 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Toronto to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Toronto to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Toronto to Chicago Flights

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*Available to One Key members.