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Cheap flights from Chicago Midway Airport to Toronto from C$ 118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Toronto departing on 31/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Toronto

Cheap round-trip flights

Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
Multiple Airlines Logo
12:50 p.m. - 10:20 p.m.YYZ-MDW
10h 30m1 stop
C$ 332Multiple Airlines
Find Deal
Fri, 31 Oct - Fri, 7 Nov
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
Multiple Airlines Logo
12:50 p.m. - 10:20 p.m.YYZ-MDW
10h 30m1 stop
C$ 334Multiple Airlines
Find Deal
Fri, 31 Oct - Fri, 7 Nov
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
Multiple Airlines Logo
12:50 p.m. - 10:20 p.m.YYZ-MDW
10h 30m1 stop
C$ 337Multiple Airlines
Find Deal
Fri, 31 Oct - Fri, 7 Nov
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
Multiple Airlines Logo
6:00 p.m. - 9:40 a.m.YYZ-MDW
16h 40m1 stop
C$ 352Multiple Airlines
Find Deal
Fri, 31 Oct - Fri, 7 Nov
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
Multiple Airlines Logo
8:00 p.m. - 6:39 p.m.YYZ-MDW
23h 39m2 stops
C$ 369Multiple Airlines
Find Deal
Fri, 31 Oct - Sun, 2 Nov
Multiple Airlines Logo
2:15 p.m. - 8:00 p.m.MDW-YYZ
28h 45m1 stop
Multiple Airlines Logo
6:30 p.m. - 9:54 a.m.YYZ-MDW
16h 24m2 stops
C$ 374Multiple Airlines
Find Deal
Thu, 4 Dec - Mon, 8 Dec
WestJet Logo
9:20 a.m. - 3:59 p.m.MDW-YYZ
5h 39m1 stop
WestJet Logo
6:20 a.m. - 1:08 p.m.YYZ-MDW
7h 48m1 stop
C$ 381WestJet
Find Deal
Sat, 1 Nov - Sat, 8 Nov
Multiple Airlines Logo
11:36 a.m. - 3:20 p.m.MDW-YYZ
26h 44m1 stop
Multiple Airlines Logo
6:30 p.m. - 9:52 a.m.YYZ-MDW
16h 22m2 stops
C$ 382Multiple Airlines
Find Deal
Sat, 1 Nov - Sat, 8 Nov
Multiple Airlines Logo
2:15 p.m. - 12:11 a.m.MDW-YYZ
8h 56m1 stop
Multiple Airlines Logo
7:40 a.m. - 9:54 a.m.YYZ-MDW
27h 14m1 stop
C$ 387Multiple Airlines
Find Deal
Thu, 4 Dec - Mon, 8 Dec
WestJet Logo
10:35 a.m. - 4:50 p.m.MDW-YYZ
5h 15m1 stop
WestJet Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
C$ 398WestJet
Find Deal
Sat, 18 Oct - Sun, 19 Oct

WestJet flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best WestJet deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets
WestJet
1 Nov
MDW9:20 a.m.Chicago Midway
5h 39m
1 stop
YYZ3:59 p.m.Toronto Pearson Intl
8 Nov
YYZ6:20 a.m.Toronto Pearson Intl
7h 48m
1 stop
MDW1:08 p.m.Chicago Midway
C$ 381
Find similar
WestJet
18 Oct
MDW10:35 a.m.Chicago Midway
5h 15m
1 stop
YYZ4:50 p.m.Toronto Pearson Intl
19 Oct
YYZ6:00 p.m.Toronto Pearson Intl
5h 14m
1 stop
MDW10:14 p.m.Chicago Midway
C$ 398
Find similar
WestJet
15 Oct
MDW9:20 a.m.Chicago Midway
14h 11m
2 stops
YYZ12:31 a.m.Toronto Pearson Intl
18 Oct
YYZ6:00 p.m.Toronto Pearson Intl
5h 14m
1 stop
MDW10:14 p.m.Chicago Midway
C$ 402
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Toronto Pearson Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 17 September 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto Pearson Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 31/10

9:32 a.m.-8:00 p.m.

1 stop9h 28m

Toronto Pearson Intl

Fri 7/11

12:50 p.m.-10:20 p.m.

1 stop10h 30m

C$ 332

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 31/10

9:32 a.m.-8:00 p.m.

1 stop9h 28m

Toronto Pearson Intl

Fri 7/11

12:50 p.m.-10:20 p.m.

1 stop10h 30m

C$ 334

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 31/10

9:32 a.m.-8:00 p.m.

1 stop9h 28m

Toronto Pearson Intl

Fri 7/11

12:50 p.m.-10:20 p.m.

1 stop10h 30m

C$ 337

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 31/10

9:32 a.m.-8:00 p.m.

1 stop9h 28m

Toronto Pearson Intl

Fri 7/11

6:00 p.m.-9:40 a.m.

1 stop16h 40m

C$ 352

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 31/10

9:32 a.m.-8:00 p.m.

1 stop9h 28m

Toronto Pearson Intl

Sun 2/11

8:00 p.m.-6:39 p.m.

2 stops23h 39m

C$ 369

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 4/12

2:15 p.m.-8:00 p.m.

1 stop28h 45m

Toronto Pearson Intl

Mon 8/12

6:30 p.m.-9:54 a.m.

2 stops16h 24m

C$ 374

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 1/11

9:20 a.m.-3:59 p.m.

1 stop5h 39m

Toronto Pearson Intl

Sat 8/11

6:20 a.m.-1:08 p.m.

1 stop7h 48m

C$ 381

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 1/11

11:36 a.m.-3:20 p.m.

1 stop26h 44m

Toronto Pearson Intl

Sat 8/11

6:30 p.m.-9:52 a.m.

2 stops16h 22m

C$ 382

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 4/12

2:15 p.m.-12:11 a.m.

1 stop8h 56m

Toronto Pearson Intl

Mon 8/12

7:40 a.m.-9:54 a.m.

1 stop27h 14m

C$ 387

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 18/10

10:35 a.m.-4:50 p.m.

1 stop5h 15m

Toronto Pearson Intl

Sun 19/10

6:00 p.m.-10:14 p.m.

1 stop5h 14m

C$ 398

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Chicago Midway Airport to Toronto Pearson Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Toronto Pearson Intl Airport?

Our data shows that Saturday is the least expensive day to fly to Toronto Pearson Intl Airport. Tickets to fly out on this day can be as low as C$ 333. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Toronto Pearson Intl Airport for around C$ 578.

What is the cheapest time of day to depart on your flight to Toronto Pearson Intl Airport?

Our data shows that the cheapest Chicago Midway Airport to Toronto Pearson Intl Airport flights are usually those with departure times in the evening. Our users have found flights to Toronto Pearson Intl Airport in the evening for as low as C$ 316. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 462 on average. Flights to Toronto Pearson Intl Airport from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

When to book flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Toronto Pearson Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Toronto Pearson Intl Airport (MDW to YYZ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Toronto Pearson Intl Airport

Direct flights

None
There are no direct flights from Chicago Midway Airport to Toronto Pearson Intl Airport. There are no popular flight routes from Chicago Midway Airport to Toronto Pearson Intl Airport.
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  • How far is Chicago Midway to Toronto Pearson Intl by plane?

    Toronto Pearson Intl is 695.6 km away from Chicago Midway. By plane, this route typically takes 5h 15m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Toronto Pearson Intl Airport?

    Prices for flights from Chicago Midway Airport to Toronto Pearson Intl Airport were last updated today.

  • How old do you have to be to fly from Chicago Midway Airport to Toronto Pearson Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Toronto Pearson Intl Airport.

  • What documentation or ID do you need to fly to Toronto Pearson Intl Airport?

    The travel and health documents you'll need for your trip to Toronto Pearson Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Toronto Pearson Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Toronto?

Book flights to Toronto if you plan to visit one of these locations
Niagara Falls
Mississauga
Brampton
Collingwood
Oshawa
Muskoka
Markham
Barrie
Niagara-on-the-Lake
Vaughan
Guelph
Brantford
Kitchener
Burlington
Orillia
Peterborough
Cambridge
St. Catharines
Gravenhurst
Oakville

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Toronto?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Toronto for you.

Can I find flights from Chicago to Toronto with flexible booking policies on momondo?

All flight searches from Chicago to Toronto on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Toronto?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Toronto from Chicago.

I’m not ready to book a flight from Chicago to Toronto right now. Can momondo alert me if prices change?

Price alerts on flights to Toronto from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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