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Cheap flights from Chicago Midway Airport to Toronto from C$ 125

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 11/12. 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

Enter your travel dates to find the best prices.
Delta Logo
1:14 p.m. - 5:15 p.m.MDW-YYZ
3h 01m1 stop
Delta Logo
6:05 a.m. - 8:54 a.m.YYZ-MDW
3h 49m1 stop
C$ 326Delta
Find Deal
Fri, 5 Dec - Sun, 7 Dec
Delta Logo
9:59 a.m. - 4:15 p.m.MDW-YYZ
5h 16m1 stop
Delta Logo
6:05 a.m. - 8:54 a.m.YYZ-MDW
3h 49m1 stop
C$ 335Delta
Find Deal
Fri, 5 Dec - Sun, 7 Dec
Delta Logo
9:34 a.m. - 2:48 p.m.MDW-YYZ
4h 14m1 stop
Delta Logo
6:30 a.m. - 1:07 p.m.YYZ-MDW
7h 37m1 stop
C$ 350Delta
Find Deal
Tue, 18 Nov - Mon, 24 Nov
Delta Logo
1:28 p.m. - 7:08 p.m.MDW-YYZ
4h 40m1 stop
Delta Logo
9:45 a.m. - 12:35 p.m.YYZ-MDW
3h 50m1 stop
C$ 366Delta
Find Deal
Fri, 6 Mar - Tue, 10 Mar
Delta Logo
1:47 p.m. - 11:21 p.m.MDW-YYZ
8h 34m1 stop
Delta Logo
12:08 p.m. - 6:08 p.m.YYZ-MDW
7h 00m1 stop
C$ 375Delta
Find Deal
Mon, 17 Nov - Thu, 20 Nov
Multiple Airlines Logo
6:37 p.m. - 12:11 a.m.MDW-YYZ
28h 34m1 stop
Multiple Airlines Logo
12:14 p.m. - 11:58 a.m.YYZ-MDW
24h 44m1 stop
C$ 401Multiple Airlines
Find Deal
Sun, 14 Dec - Thu, 1 Jan
Multiple Airlines Logo
9:07 p.m. - 2:20 p.m.MDW-YYZ
16h 13m2 stops
Multiple Airlines Logo
5:15 p.m. - 1:09 p.m.YYZ-MDW
20h 54m1 stop
C$ 417Multiple Airlines
Find Deal
Thu, 15 Jan - Mon, 19 Jan
KLM Logo
9:34 a.m. - 2:48 p.m.MDW-YYZ
4h 14m1 stop
KLM Logo
6:05 a.m. - 12:34 p.m.YYZ-MDW
7h 29m1 stop
C$ 420KLM
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Thu, 4 Dec - Sun, 7 Dec
WestJet Logo
1:47 p.m. - 11:21 p.m.MDW-YYZ
8h 34m1 stop
WestJet Logo
6:30 a.m. - 6:18 p.m.YYZ-MDW
12h 48m1 stop
C$ 423WestJet
Find Deal
Tue, 25 Nov - Fri, 28 Nov
WestJet Logo
1:47 p.m. - 11:21 p.m.MDW-YYZ
8h 34m1 stop
WestJet Logo
6:30 p.m. - 9:54 a.m.YYZ-MDW
16h 24m2 stops
C$ 424WestJet
Find Deal
Sat, 29 Nov - Mon, 1 Dec

Delta flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best Delta deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets
Delta
5 Dec
MDW1:14 p.m.Chicago Midway
3h 01m
1 stop
YYZ5:15 p.m.Toronto Pearson Intl
7 Dec
YYZ6:05 a.m.Toronto Pearson Intl
3h 49m
1 stop
MDW8:54 a.m.Chicago Midway
C$ 326
Find similar
Delta
5 Dec
MDW9:59 a.m.Chicago Midway
5h 16m
1 stop
YYZ4:15 p.m.Toronto Pearson Intl
7 Dec
YYZ6:05 a.m.Toronto Pearson Intl
3h 49m
1 stop
MDW8:54 a.m.Chicago Midway
C$ 335
Find similar
Delta
18 Nov
MDW9:34 a.m.Chicago Midway
4h 14m
1 stop
YYZ2:48 p.m.Toronto Pearson Intl
24 Nov
YYZ6:30 a.m.Toronto Pearson Intl
7h 37m
1 stop
MDW1:07 p.m.Chicago Midway
C$ 350
Find similar

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
25 Nov
MDW1:47 p.m.Chicago Midway
8h 34m
1 stop
YYZ11:21 p.m.Toronto Pearson Intl
28 Nov
YYZ6:30 a.m.Toronto Pearson Intl
12h 48m
1 stop
MDW6:18 p.m.Chicago Midway
C$ 423
Find similar
WestJet
29 Nov
MDW1:47 p.m.Chicago Midway
8h 34m
1 stop
YYZ11:21 p.m.Toronto Pearson Intl
1 Dec
YYZ6:30 p.m.Toronto Pearson Intl
16h 24m
2 stops
MDW9:54 a.m.Chicago Midway
C$ 424
Find similar
WestJet
17 Dec
MDW1:50 p.m.Chicago Midway
8h 37m
1 stop
YYZ11:27 p.m.Toronto Pearson Intl
24 Dec
YYZ12:14 p.m.Toronto Pearson Intl
21h 51m
1 stop
MDW9:05 a.m.Chicago Midway
C$ 437
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 3 November 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 5/12

1:14 p.m.-5:15 p.m.

1 stop3h 01m

Toronto Pearson Intl

Sun 7/12

6:05 a.m.-8:54 a.m.

1 stop3h 49m

C$ 326

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 5/12

9:59 a.m.-4:15 p.m.

1 stop5h 16m

Toronto Pearson Intl

Sun 7/12

6:05 a.m.-8:54 a.m.

1 stop3h 49m

C$ 335

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 18/11

9:34 a.m.-2:48 p.m.

1 stop4h 14m

Toronto Pearson Intl

Mon 24/11

6:30 a.m.-1:07 p.m.

1 stop7h 37m

C$ 350

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 6/3

1:28 p.m.-7:08 p.m.

1 stop4h 40m

Toronto Pearson Intl

Tue 10/3

9:45 a.m.-12:35 p.m.

1 stop3h 50m

C$ 366

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 17/11

1:47 p.m.-11:21 p.m.

1 stop8h 34m

Toronto Pearson Intl

Thu 20/11

12:08 p.m.-6:08 p.m.

1 stop7h 00m

C$ 375

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 14/12

6:37 p.m.-12:11 a.m.

1 stop28h 34m

Toronto Pearson Intl

Thu 1/1

12:14 p.m.-11:58 a.m.

1 stop24h 44m

C$ 401

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 15/1

9:07 p.m.-2:20 p.m.

2 stops16h 13m

Toronto Pearson Intl

Mon 19/1

5:15 p.m.-1:09 p.m.

1 stop20h 54m

C$ 417

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 4/12

9:34 a.m.-2:48 p.m.

1 stop4h 14m

Toronto Pearson Intl

Sun 7/12

6:05 a.m.-12:34 p.m.

1 stop7h 29m

C$ 420

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 25/11

1:47 p.m.-11:21 p.m.

1 stop8h 34m

Toronto Pearson Intl

Fri 28/11

6:30 a.m.-6:18 p.m.

1 stop12h 48m

C$ 423

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 29/11

1:47 p.m.-11:21 p.m.

1 stop8h 34m

Toronto Pearson Intl

Mon 1/12

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

2 stops16h 24m

C$ 424

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 Thursday 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$ 327. 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$ 516.

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$ 314. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 475 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 3h 01m.

  • 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
Barrie
Markham
Guelph
Niagara-on-the-Lake
Vaughan
Kitchener
Brantford
Burlington
Orillia
Peterborough
Cambridge
Gravenhurst
St. Catharines
Pickering

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.

An easier way to manage your Toronto Pearson Intl Airport trip

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