Find flights
When to book
FAQs

Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 199

YYZ — MDW
4 Oct — 11 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Pearson Intl to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Pearson Intl to Midway

Thu 24/96:00 a.m. -
1 stop4h 07m
Sun 27/99:29 a.m. -
1 stop6h 51m
Deal found 2/9C$ 316
Thu 24/96:00 a.m. -
1 stop4h 07m
Wed 30/99:29 a.m. -
1 stop6h 51m
Deal found 1/9C$ 318
Mon 21/94:05 p.m. -
1 stop3h 28m
Wed 23/99:29 a.m. -
1 stop6h 51m
Deal found 31/8C$ 329
Fri 25/92:24 p.m. -
1 stop5h 09m
Sun 27/99:29 a.m. -
1 stop4h 46m
Deal found 2/9C$ 344
Thu 24/96:07 a.m. -
1 stop4h 07m
Thu 1/109:36 a.m. -
1 stop6h 51m
Deal found 3/9C$ 363
Sat 26/99:52 a.m. -
1 stop3h 54m
Tue 29/99:36 a.m. -
1 stop6h 51m
Deal found 1/9C$ 364
Fri 25/92:24 p.m. -
1 stop5h 09m
Sat 26/96:40 p.m. -
1 stop3h 19m
Deal found 30/8C$ 376
Sat 19/96:00 a.m. -
1 stop4h 07m
Wed 23/99:29 a.m. -
1 stop6h 51m
Deal found 1/9C$ 381
Wed 25/116:00 a.m. -
1 stop4h 42m
Sun 17/19:30 a.m. -
1 stop5h 34m
Deal found 2/9C$ 385
Tue 22/96:07 a.m. -
1 stop7h 39m
Sat 26/99:36 a.m. -
1 stop4h 46m
Deal found 31/8C$ 392

Find flight deals from Pearson Intl to Midway

Round-trip from

C$ 316

One-way from

C$ 199

Popular in

April

Cheapest in

December

Average price

C$ 475
Delta
  • Delta
  • 24/9-27/9
  • 2 total stops
  • 14h 30m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 23/9-31/12
  • 1 total stop
  • 4h 07m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 149 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 1/10

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 25/9

2:24 p.m.-6:33 p.m.

1 stop5h 09m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 23/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 12/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 22/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 14/10

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 27/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 249
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 15/9

4:05 p.m.-6:33 p.m.

1 stop3h 28m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 264

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 19/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 265

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 24/9

6:00 a.m.-12:39 p.m.

1 stop7h 39m

Chicago Midway

Sun 27/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 316

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Best time to book a flight from Pearson Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pearson Intl with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago Midway Airport

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Toronto Pearson Intl Airport to Chicago Midway Airport flights typically cost between C$ 417 and C$ 580 in September.
The cheapest round-trip price found within the last 5 days was C$ 316 on Delta (24 Sep-27 Sep).

Related info for your journey

  • How long is the flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

    Airlines like Delta fly from Toronto Pearson Intl Airport to Chicago Midway Airport in about 7h 39m. The time it takes to get you to your destination can typically vary by up to . The distance from Toronto Pearson Intl Airport to Chicago Midway Airport is about 695 km.

  • Can I find deals for flights from Pearson Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Pearson Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pearson Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Midway.

  • Can I find deals for business class flights from Pearson Intl to Midway?

    Yes. Cheapflights offers flight deals from Pearson Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Pearson Intl to Midway

Pearson Intl to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Toronto Island to Midway flights
Hamilton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights

Fly with Cheapflights

How does Cheapflights help users find flights from Pearson Intl to Midway?

Cheapflights makes it easy to find Pearson Intl to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Pearson Intl to Midway.

Can Cheapflights find flights from Pearson Intl to Midway with no change fees?

Yes, we can. To see specific flights from Pearson Intl to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Pearson Intl to Midway become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Pearson Intl today and book when prices fit your budget.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.