S$178 Cheap Flights from Toronto to Chicago

View S$178 flight on Thu, 5 Feb, 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 to Chicago (YYZ-MDW)

Prices were available within the past 7 days and start at S$178 for one-way flights and S$331 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
MDW
Chicago
S$331 Return, found 2 days ago
S$331
Return
found 2 days ago
Select Delta flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$331 found 2 days ago
Delta
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
MDW
Chicago
S$380 Return, found 2 days ago
S$380
Return
found 2 days ago
Select Delta flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$380 found 2 days ago
Delta
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
MDW
Chicago
S$400 Return, found 2 days ago
S$400
Return
found 2 days ago
Select Delta flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$400 found 2 days ago
Delta
Thu, 15 Jan - Thu, 22 Jan
YYZ
Toronto
MDW
Chicago
S$409 Return, found 3 days ago
S$409
Return
found 3 days ago
Select Delta flight, departing Thu, 15 Jan from Toronto to Chicago, returning Thu, 22 Jan, priced at S$409 found 3 days ago
Delta
Wed, 18 Mar - Tue, 31 Mar
YYZ
Toronto
MDW
Chicago
S$447 Return, found 3 days ago
S$447
Return
found 3 days ago
Select Delta flight, departing Wed, 18 Mar from Toronto to Chicago, returning Tue, 31 Mar, priced at S$447 found 3 days ago
Delta
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
MDW
Chicago
S$448 Return, found 2 days ago
S$448
Return
found 2 days ago
Select Delta flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$448 found 2 days ago
Delta
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
MDW
Chicago
S$459 Return, found 2 days ago
S$459
Return
found 2 days ago
Select Delta flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$459 found 2 days ago
Delta
Thu, 15 Jan - Thu, 22 Jan
YYZ
Toronto
MDW
Chicago
S$479 Return, found 3 days ago
S$479
Return
found 3 days ago
Select Delta flight, departing Thu, 15 Jan from Toronto to Chicago, returning Thu, 22 Jan, priced at S$479 found 3 days ago
Delta
Mon, 10 Aug - Mon, 24 Aug
YYZ
Toronto
MDW
Chicago
S$482 Return, found 3 days ago
S$482
Return
found 3 days ago
Select Delta flight, departing Mon, 10 Aug from Toronto to Chicago, returning Mon, 24 Aug, priced at S$482 found 3 days ago
Delta
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
MDW
Chicago
S$508 Return, found 2 days ago
S$508
Return
found 2 days ago
Select Delta flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$508 found 2 days ago

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

February is typically the cheapest month to fly

From S$271 - S$473 per traveller.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city centre is 16 minutes. Flights from S$331
MDW
Midway Intl.
CheapestClosest
Average driving time to city centre16 min
Flights from S$331

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 S$331. 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 kilometres. 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.

Travel information

Origin airport
Pearson Intl.
Destination airport
Midway Intl.
Return price
S$330
Distance
692 km

Book with confidence

Perfect flights from Toronto to Chicago

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Experience the joy of finding cheap flights from Pearson Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$178 and roundtrip prices from S$331*.
 

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Toronto to Chicago

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