NT$4,321 Cheap Flights from Toronto (YYZ) to Chicago (MDW)

View NT$4,321 flight on Sun, 2026/2/22Opens 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 to Chicago (YYZ-MDW)

Prices were available within the past 7 days and start at NT$4,321 for one-way flights and NT$6,799 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Feb 5 - Sun, Feb 8
YYZ
Toronto
MDW
Chicago
NT$6,799 Roundtrip, found 2 days ago
NT$6,799
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Feb 5 from Toronto to Chicago, returning Sun, Feb 8, priced at NT$6,799 found 2 days ago
Delta
Thu, Feb 5 - Sun, Feb 8
YYZ
Toronto
MDW
Chicago
NT$13,783 Roundtrip, found 2 days ago
NT$13,783
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Feb 5 from Toronto to Chicago, returning Sun, Feb 8, priced at NT$13,783 found 2 days ago
Flights from Toronto (YYZ) to Chicago (MDW)
Origin airport
Pearson Intl.
Destination airport
Midway Intl.
Roundtrip price
NT$6,799
Distance
692 km

Toronto to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Toronto to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with YYZ to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Toronto for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from Toronton Pearson to MDW?
Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip flights from YYZ to Midway Intl. Airport (MDW) start from NT$6,799. Book today to secure the best price for your exciting adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Toronton Pearson to Chicago Airport?
This can differ from airline to airline, as each has its own set of terms and conditions. Visit the Customer Service Portal, where there are simple instructions on how to cancel your flight online.
How do I find cheap flights from Toronto Pearson Airport to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from YYZ to Midway Intl. Airport (MDW)?
The flight distance from Pearson Intl. Airport (YYZ) (YYZ) to Midway Intl. Airport (MDW) (MDW) is 700 kilometers. You'll be walking down the air bridge and picking up your bags from the carousel in no time.
Which airlines fly direct from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
At the moment, no airlines offer direct flights from Pearson Intl. Airport (YYZ) to Chicago Airport. You'll have to book a flight with one or more stops. To get the best connections and price, lock in your airfare ahead of time.
Are Pearson Intl. Airport (YYZ) to MDW flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally pick up a bargain, with some of the cheapest fares from Toronton Pearson to MDW arising a few weeks prior to the departure date. If you'd rather plan ahead of time, Expedia compares and updates all the best flight deals continuously — as early as 12 months in advance in some cases. It does depend on the carrier though, as not every airline advertises prices that far in advance.

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