Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport to Toronto from C$ 138

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 12/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
9:35 a.m. - 5:17 p.m.
MDW
-
YYZ
6h 42m
1 stop
Delta Logo
6:20 a.m. - 8:53 a.m.
YYZ
-
MDW
3h 33m
1 stop
C$ 357Delta
Wed, 18 Mar - Mon, 23 Mar
KLM Logo
9:50 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 09m
1 stop
KLM Logo
6:30 a.m. - 1:05 p.m.
YYZ
-
MDW
7h 35m
1 stop
C$ 405KLM
Thu, 26 Feb - Sun, 1 Mar
Delta Logo
9:23 a.m. - 6:31 p.m.
MDW
-
YYZ
8h 08m
1 stop
Delta Logo
6:10 a.m. - 12:42 p.m.
YYZ
-
MDW
7h 32m
1 stop
C$ 408Delta
Mon, 25 May - Thu, 28 May
Multiple Airlines Logo
9:51 p.m. - 8:10 p.m.
MDW
-
YYZ
21h 19m
2 stops
Multiple Airlines Logo
12:15 p.m. - 5:54 p.m.
YYZ
-
MDW
6h 39m
1 stop
C$ 443Multiple Airlines
Mon, 9 Mar - Thu, 12 Mar
WestJet Logo
9:30 a.m. - 3:18 p.m.
MDW
-
YYZ
4h 48m
1 stop
WestJet Logo
3:59 p.m. - 6:31 p.m.
YYZ
-
MDW
3h 32m
1 stop
C$ 450WestJet
Sat, 25 Jul - Sat, 1 Aug
WestJet Logo
9:30 a.m. - 3:18 p.m.
MDW
-
YYZ
4h 48m
1 stop
WestJet Logo
9:45 a.m. - 12:30 p.m.
YYZ
-
MDW
3h 45m
1 stop
C$ 452WestJet
Tue, 23 Jun - Tue, 7 Jul
WestJet Logo
9:30 a.m. - 3:18 p.m.
MDW
-
YYZ
4h 48m
1 stop
WestJet Logo
6:00 a.m. - 12:30 p.m.
YYZ
-
MDW
7h 30m
1 stop
C$ 453WestJet
Sat, 27 Jun - Tue, 30 Jun
WestJet Logo
9:31 a.m. - 11:59 p.m.
MDW
-
YYZ
13h 28m
2 stops
WestJet Logo
6:10 a.m. - 8:47 a.m.
YYZ
-
MDW
3h 37m
1 stop
C$ 454WestJet
Wed, 29 Apr - Sat, 2 May
WestJet Logo
6:20 p.m. - 9:02 a.m.
MDW
-
YYZ
13h 42m
1 stop
WestJet Logo
12:20 p.m. - 5:45 p.m.
YYZ
-
MDW
6h 25m
1 stop
C$ 456WestJet
Wed, 25 Feb - Thu, 26 Feb
WestJet Logo
6:20 p.m. - 10:40 p.m.
MDW
-
YYZ
3h 20m
1 stop
WestJet Logo
3:59 p.m. - 8:53 a.m.
YYZ
-
MDW
17h 54m
1 stop
C$ 457WestJet
Wed, 4 Mar - Wed, 11 Mar

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 Jul
MDW9:30 a.m.Chicago Midway
4h 48m
1 stop
YYZ3:18 p.m.Toronto Pearson Intl
1 Aug
YYZ3:59 p.m.Toronto Pearson Intl
3h 32m
1 stop
MDW6:31 p.m.Chicago Midway
C$ 450
WestJet
23 Jun
MDW1:00 p.m.Chicago Midway
3h 23m
1 stop
YYZ5:23 p.m.Toronto Pearson Intl
28 Jun
YYZ6:00 a.m.Toronto Pearson Intl
3h 42m
1 stop
MDW8:42 a.m.Chicago Midway
C$ 452
WestJet
27 Jun
MDW1:00 p.m.Chicago Midway
3h 23m
1 stop
YYZ5:23 p.m.Toronto Pearson Intl
30 Jun
YYZ6:00 a.m.Toronto Pearson Intl
7h 30m
1 stop
MDW12:30 p.m.Chicago Midway
C$ 453

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
18 Mar
MDW9:35 a.m.Chicago Midway
6h 42m
1 stop
YYZ5:17 p.m.Toronto Pearson Intl
21 Mar
YYZ6:20 a.m.Toronto Pearson Intl
3h 33m
1 stop
MDW8:53 a.m.Chicago Midway
C$ 357
Delta
25 May
MDW9:23 a.m.Chicago Midway
8h 08m
1 stop
YYZ6:31 p.m.Toronto Pearson Intl
28 May
YYZ6:10 a.m.Toronto Pearson Intl
7h 32m
1 stop
MDW12:42 p.m.Chicago Midway
C$ 408
Delta
20 Mar
MDW2:05 p.m.Chicago Midway
8h 01m
1 stop
YYZ11:06 p.m.Toronto Pearson Intl
26 Mar
YYZ6:20 a.m.Toronto Pearson Intl
7h 09m
1 stop
MDW12:29 p.m.Chicago Midway
C$ 460

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 6 February 2026.
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 18/3

9:35 a.m.-5:17 p.m.

1 stop6h 42m

Toronto Pearson Intl

Mon 23/3

6:20 a.m.-8:53 a.m.

1 stop3h 33m

C$ 357

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 26/2

9:50 a.m.-3:59 p.m.

1 stop5h 09m

Toronto Pearson Intl

Sun 1/3

6:30 a.m.-1:05 p.m.

1 stop7h 35m

C$ 405

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 25/5

9:23 a.m.-6:31 p.m.

1 stop8h 08m

Toronto Pearson Intl

Thu 28/5

6:10 a.m.-12:42 p.m.

1 stop7h 32m

C$ 408

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 9/3

9:51 p.m.-8:10 p.m.

2 stops21h 19m

Toronto Pearson Intl

Thu 12/3

12:15 p.m.-5:54 p.m.

1 stop6h 39m

C$ 443

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 25/7

9:30 a.m.-3:18 p.m.

1 stop4h 48m

Toronto Pearson Intl

Sat 1/8

3:59 p.m.-6:31 p.m.

1 stop3h 32m

C$ 450

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 23/6

9:30 a.m.-3:18 p.m.

1 stop4h 48m

Toronto Pearson Intl

Tue 7/7

9:45 a.m.-12:30 p.m.

1 stop3h 45m

C$ 452

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 27/6

9:30 a.m.-3:18 p.m.

1 stop4h 48m

Toronto Pearson Intl

Tue 30/6

6:00 a.m.-12:30 p.m.

1 stop7h 30m

C$ 453

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 29/4

9:31 a.m.-11:59 p.m.

2 stops13h 28m

Toronto Pearson Intl

Sat 2/5

6:10 a.m.-8:47 a.m.

1 stop3h 37m

C$ 454

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 25/2

6:20 p.m.-9:02 a.m.

1 stop13h 42m

Toronto Pearson Intl

Thu 26/2

12:20 p.m.-5:45 p.m.

1 stop6h 25m

C$ 456

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 4/3

6:20 p.m.-10:40 p.m.

1 stop3h 20m

Toronto Pearson Intl

Wed 11/3

3:59 p.m.-8:53 a.m.

1 stop17h 54m

C$ 457

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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$ 325. 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$ 504.

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$ 283. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 456 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 05m

Direct flights

None
The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 05m
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 05m.

  • 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
Markham
Muskoka
Vaughan
Barrie
Kitchener
Niagara-on-the-Lake
Orillia
Burlington
Brantford
Cambridge
Pickering
Peterborough
Waterloo
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.

An easier way to manage your Toronto Pearson Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 8/3
Sun 15/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Toronto