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Cheap flights from Chicago Midway Airport to Toronto from C$ 130

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 21/2. 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
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
Delta Logo
7:45 a.m. - 12:46 p.m.
YYZ
-
MDW
6h 01m1 stop
C$ 322Delta
Thu, 5 Feb - Mon, 9 Feb
Delta Logo
1:26 p.m. - 10:42 p.m.
MDW
-
YYZ
8h 16m1 stop
Delta Logo
6:30 a.m. - 11:05 a.m.
YYZ
-
MDW
5h 35m1 stop
C$ 338Delta
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
1:26 p.m. - 7:08 p.m.
MDW
-
YYZ
4h 42m1 stop
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
C$ 346Delta
Thu, 29 Jan - Thu, 5 Feb
Delta Logo
1:26 p.m. - 7:08 p.m.
MDW
-
YYZ
4h 42m1 stop
Delta Logo
6:30 a.m. - 11:05 a.m.
YYZ
-
MDW
5h 35m1 stop
C$ 361Delta
Sat, 31 Jan - Sat, 7 Feb
Delta Logo
1:49 p.m. - 11:13 p.m.
MDW
-
YYZ
8h 24m1 stop
Delta Logo
6:05 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 47m1 stop
C$ 369Delta
Fri, 16 Jan - Mon, 19 Jan
Delta Logo
1:49 p.m. - 11:13 p.m.
MDW
-
YYZ
8h 24m1 stop
Delta Logo
7:45 a.m. - 12:46 p.m.
YYZ
-
MDW
6h 01m1 stop
C$ 384Delta
Thu, 15 Jan - Fri, 23 Jan
Multiple Airlines Logo
4:31 p.m. - 2:16 p.m.
MDW
-
YYZ
20h 45m1 stop
Multiple Airlines Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
C$ 402Multiple Airlines
Mon, 12 Jan - Fri, 16 Jan
Multiple Airlines Logo
4:31 p.m. - 2:05 p.m.
MDW
-
YYZ
20h 34m1 stop
Multiple Airlines Logo
6:05 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 47m1 stop
C$ 412Multiple Airlines
Mon, 12 Jan - Mon, 19 Jan
WestJet Logo
6:14 p.m. - 9:04 a.m.
MDW
-
YYZ
13h 50m1 stop
WestJet Logo
10:05 a.m. - 12:48 p.m.
YYZ
-
MDW
3h 43m1 stop
C$ 416WestJet
Wed, 7 Jan - Fri, 9 Jan
WestJet Logo
1:28 p.m. - 7:13 p.m.
MDW
-
YYZ
4h 45m1 stop
WestJet Logo
12:10 p.m. - 5:34 p.m.
YYZ
-
MDW
6h 24m1 stop
C$ 417WestJet
Thu, 8 Jan - Tue, 13 Jan

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 Feb
MDW9:53 a.m.Chicago Midway
5h 06m
1 stop
YYZ3:59 p.m.Toronto Pearson Intl
9 Feb
YYZ10:05 a.m.Toronto Pearson Intl
3h 41m
1 stop
MDW12:46 p.m.Chicago Midway
C$ 322
Find similar
Delta
5 Feb
MDW9:53 a.m.Chicago Midway
5h 06m
1 stop
YYZ3:59 p.m.Toronto Pearson Intl
8 Feb
YYZ6:00 a.m.Toronto Pearson Intl
3h 52m
1 stop
MDW8:52 a.m.Chicago Midway
C$ 338
Find similar
Delta
29 Jan
MDW1:26 p.m.Chicago Midway
4h 42m
1 stop
YYZ7:08 p.m.Toronto Pearson Intl
3 Feb
YYZ12:12 p.m.Toronto Pearson Intl
6h 43m
1 stop
MDW5:55 p.m.Chicago Midway
C$ 346
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
7 Jan
MDW6:14 p.m.Chicago Midway
13h 50m
1 stop
YYZ9:04 a.m.Toronto Pearson Intl
9 Jan
YYZ10:05 a.m.Toronto Pearson Intl
3h 43m
1 stop
MDW12:48 p.m.Chicago Midway
C$ 416
Find similar
WestJet
8 Jan
MDW6:14 p.m.Chicago Midway
3h 27m
1 stop
YYZ10:41 p.m.Toronto Pearson Intl
14 Jan
YYZ10:05 a.m.Toronto Pearson Intl
3h 43m
1 stop
MDW12:48 p.m.Chicago Midway
C$ 417
Find similar
WestJet
14 Jan
MDW6:14 p.m.Chicago Midway
3h 27m
1 stop
YYZ10:41 p.m.Toronto Pearson Intl
21 Jan
YYZ12:21 p.m.Toronto Pearson Intl
6h 08m
1 stop
MDW5:29 p.m.Chicago Midway
C$ 419
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 18 December 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

Thu 5/2

9:33 a.m.-4:12 p.m.

1 stop5h 39m

Toronto Pearson Intl

Mon 9/2

7:45 a.m.-12:46 p.m.

1 stop6h 01m

C$ 322

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/2

1:26 p.m.-10:42 p.m.

1 stop8h 16m

Toronto Pearson Intl

Sun 8/2

6:30 a.m.-11:05 a.m.

1 stop5h 35m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 29/1

1:26 p.m.-7:08 p.m.

1 stop4h 42m

Toronto Pearson Intl

Thu 5/2

6:00 a.m.-8:52 a.m.

1 stop3h 52m

C$ 346

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 31/1

1:26 p.m.-7:08 p.m.

1 stop4h 42m

Toronto Pearson Intl

Sat 7/2

6:30 a.m.-11:05 a.m.

1 stop5h 35m

C$ 361

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 16/1

1:49 p.m.-11:13 p.m.

1 stop8h 24m

Toronto Pearson Intl

Mon 19/1

6:05 a.m.-8:52 a.m.

1 stop3h 47m

C$ 369

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 15/1

1:49 p.m.-11:13 p.m.

1 stop8h 24m

Toronto Pearson Intl

Fri 23/1

7:45 a.m.-12:46 p.m.

1 stop6h 01m

C$ 384

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 12/1

4:31 p.m.-2:16 p.m.

1 stop20h 45m

Toronto Pearson Intl

Fri 16/1

6:00 a.m.-8:52 a.m.

1 stop3h 52m

C$ 402

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 12/1

4:31 p.m.-2:05 p.m.

1 stop20h 34m

Toronto Pearson Intl

Mon 19/1

6:05 a.m.-8:52 a.m.

1 stop3h 47m

C$ 412

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 7/1

6:14 p.m.-9:04 a.m.

1 stop13h 50m

Toronto Pearson Intl

Fri 9/1

10:05 a.m.-12:48 p.m.

1 stop3h 43m

C$ 416

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 8/1

1:28 p.m.-7:13 p.m.

1 stop4h 45m

Toronto Pearson Intl

Tue 13/1

12:10 p.m.-5:34 p.m.

1 stop6h 24m

C$ 417

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Toronto from

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$ 330. 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$ 462.

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 afternoon. Our users have found flights to Toronto Pearson Intl Airport in the afternoon for as low as C$ 298. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 463 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

Fastest flight time

3h 07m

Direct flights

None
The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 07m
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.
Search flight deals

  • 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 07m.

  • 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
Guelph
Muskoka
Barrie
Markham
Niagara-on-the-Lake
Vaughan
Kitchener
Burlington
Orillia
Brantford
Cambridge
Peterborough
Pickering
Oakville
Gravenhurst

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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