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Cheap flights from Chicago Midway Airport to Toronto from C$ 123

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 16/9. 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

Delta Logo
9:30 a.m. - 5:23 p.m.MDW-YYZ
6h 53m1 stop
Delta Logo
6:00 a.m. - 1:03 p.m.YYZ-MDW
8h 03m1 stop
C$ 322Delta
Find Deal
Wed, 10 Sep - Sat, 13 Sep
Delta Logo
9:35 a.m. - 5:19 p.m.MDW-YYZ
6h 44m1 stop
Delta Logo
4:12 p.m. - 6:35 p.m.YYZ-MDW
3h 23m1 stop
C$ 324Delta
Find Deal
Sat, 13 Sep - Tue, 16 Sep
Delta Logo
9:31 a.m. - 5:23 p.m.MDW-YYZ
6h 52m1 stop
Delta Logo
4:12 p.m. - 6:35 p.m.YYZ-MDW
3h 23m1 stop
C$ 336Delta
Find Deal
Wed, 20 Aug - Fri, 12 Sep
Delta Logo
1:08 p.m. - 5:23 p.m.MDW-YYZ
3h 15m1 stop
Delta Logo
12:14 p.m. - 6:35 p.m.YYZ-MDW
7h 21m1 stop
C$ 347Delta
Find Deal
Wed, 24 Sep - Sun, 28 Sep
Delta Logo
9:31 a.m. - 1:32 p.m.MDW-YYZ
3h 01m1 stop
Delta Logo
4:12 p.m. - 6:35 p.m.YYZ-MDW
3h 23m1 stop
C$ 371Delta
Find Deal
Sun, 7 Sep - Fri, 12 Sep
Delta Logo
9:30 a.m. - 1:32 p.m.MDW-YYZ
3h 02m1 stop
Delta Logo
4:12 p.m. - 6:35 p.m.YYZ-MDW
3h 23m1 stop
C$ 376Delta
Find Deal
Mon, 8 Sep - Tue, 16 Sep
Delta Logo
1:43 p.m. - 11:33 p.m.MDW-YYZ
8h 50m1 stop
Delta Logo
2:50 p.m. - 6:37 p.m.YYZ-MDW
4h 47m1 stop
C$ 415Delta
Find Deal
Wed, 3 Sep - Fri, 5 Sep
WestJet Logo
12:43 p.m. - 9:58 p.m.MDW-YYZ
8h 15m1 stop
WestJet Logo
11:33 a.m. - 9:44 p.m.YYZ-MDW
11h 11m1 stop
C$ 421WestJet
Find Deal
Thu, 21 Aug - Fri, 22 Aug
Delta Logo
1:43 p.m. - 11:31 p.m.MDW-YYZ
8h 48m1 stop
Delta Logo
12:14 p.m. - 6:35 p.m.YYZ-MDW
7h 21m1 stop
C$ 429Delta
Find Deal
Tue, 12 Aug - Fri, 12 Sep
WestJet Logo
9:20 a.m. - 6:28 p.m.MDW-YYZ
8h 08m1 stop
WestJet Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
C$ 432WestJet
Find Deal
Wed, 1 Oct - Mon, 6 Oct

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
10 Sep
MDW9:30 a.m.Chicago Midway
6h 53m
1 stop
YYZ5:23 p.m.Toronto Pearson Intl
13 Sep
YYZ6:00 a.m.Toronto Pearson Intl
8h 03m
1 stop
MDW1:03 p.m.Chicago Midway
C$ 322
Find similar
Delta
13 Sep
MDW9:35 a.m.Chicago Midway
6h 44m
1 stop
YYZ5:19 p.m.Toronto Pearson Intl
16 Sep
YYZ4:12 p.m.Toronto Pearson Intl
3h 23m
1 stop
MDW6:35 p.m.Chicago Midway
C$ 324
Find similar
Delta
20 Aug
MDW9:31 a.m.Chicago Midway
6h 52m
1 stop
YYZ5:23 p.m.Toronto Pearson Intl
12 Sep
YYZ4:12 p.m.Toronto Pearson Intl
3h 23m
1 stop
MDW6:35 p.m.Chicago Midway
C$ 336
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
21 Aug
MDW12:43 p.m.Chicago Midway
8h 15m
1 stop
YYZ9:58 p.m.Toronto Pearson Intl
22 Aug
YYZ11:33 a.m.Toronto Pearson Intl
11h 11m
1 stop
MDW9:44 p.m.Chicago Midway
C$ 421
Find similar
WestJet
1 Oct
MDW9:20 a.m.Chicago Midway
8h 08m
1 stop
YYZ6:28 p.m.Toronto Pearson Intl
6 Oct
YYZ6:00 p.m.Toronto Pearson Intl
5h 14m
1 stop
MDW10:14 p.m.Chicago Midway
C$ 432
Find similar
WestJet
21 Aug
MDW12:43 p.m.Chicago Midway
8h 15m
1 stop
YYZ9:58 p.m.Toronto Pearson Intl
24 Aug
YYZ6:07 p.m.Toronto Pearson Intl
16h 29m
1 stop
MDW9:36 a.m.Chicago Midway
C$ 441
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 31 July 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

Wed 10/9

9:30 a.m.-5:23 p.m.

1 stop6h 53m

Toronto Pearson Intl

Sat 13/9

6:00 a.m.-1:03 p.m.

1 stop8h 03m

C$ 322

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 13/9

9:35 a.m.-5:19 p.m.

1 stop6h 44m

Toronto Pearson Intl

Tue 16/9

4:12 p.m.-6:35 p.m.

1 stop3h 23m

C$ 324

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 20/8

9:31 a.m.-5:23 p.m.

1 stop6h 52m

Toronto Pearson Intl

Fri 12/9

4:12 p.m.-6:35 p.m.

1 stop3h 23m

C$ 336

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 24/9

1:08 p.m.-5:23 p.m.

1 stop3h 15m

Toronto Pearson Intl

Sun 28/9

12:14 p.m.-6:35 p.m.

1 stop7h 21m

C$ 347

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 7/9

9:31 a.m.-1:32 p.m.

1 stop3h 01m

Toronto Pearson Intl

Fri 12/9

4:12 p.m.-6:35 p.m.

1 stop3h 23m

C$ 371

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 8/9

9:30 a.m.-1:32 p.m.

1 stop3h 02m

Toronto Pearson Intl

Tue 16/9

4:12 p.m.-6:35 p.m.

1 stop3h 23m

C$ 376

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 3/9

1:43 p.m.-11:33 p.m.

1 stop8h 50m

Toronto Pearson Intl

Fri 5/9

2:50 p.m.-6:37 p.m.

1 stop4h 47m

C$ 415

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 21/8

12:43 p.m.-9:58 p.m.

1 stop8h 15m

Toronto Pearson Intl

Fri 22/8

11:33 a.m.-9:44 p.m.

1 stop11h 11m

C$ 421

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 12/8

1:43 p.m.-11:31 p.m.

1 stop8h 48m

Toronto Pearson Intl

Fri 12/9

12:14 p.m.-6:35 p.m.

1 stop7h 21m

C$ 429

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 1/10

9:20 a.m.-6:28 p.m.

1 stop8h 08m

Toronto Pearson Intl

Mon 6/10

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

1 stop5h 14m

C$ 432

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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$ 363. 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$ 581.

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$ 345. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 466 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

Best price found

C$ 123

Fastest flight time

3h 01m

Direct flights

None
The best one-way flight to Toronto Pearson Intl Airport from Chicago Midway Airport in the past 72 hours is C$ 123. The best round-trip flight deal from Chicago Midway Airport to Toronto Pearson Intl Airport found on momondo in the last 72 hours is C$ 322.
The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 01m
There are no direct flights from Chicago Midway Airport to Toronto Pearson Intl Airport. Popular non-direct route for this connection is Chicago Midway Airport - 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
Markham
Muskoka
Barrie
Niagara-on-the-Lake
Vaughan
Guelph
Brantford
Kitchener
Burlington
Orillia
Peterborough
Cambridge
Gravenhurst
Oakville
St. Catharines

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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