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Cheap flights from Chicago Midway Airport to Canada from C$ 93

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 Canada departing on 22/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from Chicago Midway Airport to Canada

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 265Porter Airlines
Thu, 5 Feb - Fri, 6 Feb
Porter Airlines Logo
11:05 a.m. - 5:45 p.m.
MDW
-
YUL
5h 40m
1 stop
Porter Airlines Logo
10:15 a.m. - 3:20 p.m.
YUL
-
MDW
6h 05m
1 stop
C$ 267Porter Airlines
Fri, 6 Feb - Sun, 8 Feb
Porter Airlines Logo
11:05 a.m. - 5:45 p.m.
MDW
-
YUL
5h 40m
1 stop
Porter Airlines Logo
10:15 a.m. - 3:20 p.m.
YUL
-
MDW
6h 05m
1 stop
C$ 269Porter Airlines
Fri, 6 Feb - Sun, 8 Feb
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 275Porter Airlines
Wed, 11 Feb - Tue, 17 Feb
Multiple Airlines Logo
12:50 p.m. - 3:32 p.m.
MDW
-
YTZ
1h 42mdirect
Multiple Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 286Multiple Airlines
Sat, 14 Feb - Wed, 18 Feb
Multiple Airlines Logo
3:24 p.m. - 11:59 p.m.
MDW
-
YVR
10h 35m
1 stop
Multiple Airlines Logo
11:00 p.m. - 4:16 p.m.
YVR
-
MDW
15h 16m
1 stop
C$ 332Multiple Airlines
Mon, 23 Feb - Wed, 25 Feb
Delta Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m
1 stop
Delta Logo
6:30 a.m. - 11:05 a.m.
YYZ
-
MDW
5h 35m
1 stop
C$ 346Delta
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
1:26 p.m. - 7:08 p.m.
MDW
-
YYZ
4h 42m
1 stop
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m
1 stop
C$ 355Delta
Thu, 5 Feb - Sun, 8 Feb
WestJet Logo
9:50 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 09m
1 stop
WestJet Logo
12:15 p.m. - 5:54 p.m.
YYZ
-
MDW
6h 39m
1 stop
C$ 393WestJet
Sun, 1 Mar - Sun, 8 Mar
WestJet Logo
9:34 a.m. - 4:10 p.m.
MDW
-
YYZ
5h 36m
1 stop
WestJet Logo
6:10 a.m. - 8:54 a.m.
YYZ
-
MDW
3h 44m
1 stop
C$ 418WestJet
Fri, 27 Feb - Fri, 6 Mar

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets
WestJet
1 Mar
MDW9:50 a.m.Chicago Midway
5h 09m
1 stop
YYZ3:59 p.m.Toronto Pearson Intl
8 Mar
YYZ12:15 p.m.Toronto Pearson Intl
6h 39m
1 stop
MDW5:54 p.m.Chicago Midway
C$ 393
WestJet
6 Feb
MDW10:48 a.m.Chicago Midway
12h 10m
1 stop
YYZ11:58 p.m.Toronto Pearson Intl
11 Feb
YYZ12:21 p.m.Toronto Pearson Intl
6h 08m
1 stop
MDW5:29 p.m.Chicago Midway
C$ 422
WestJet
5 Feb
MDW10:48 a.m.Chicago Midway
5h 16m
1 stop
YYZ5:04 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$ 425

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets
Delta
4 Feb
MDW10:46 a.m.Chicago Midway
5h 09m
1 stop
YUL4:55 p.m.Montreal Pierre Elliott Trudeau Intl
6 Feb
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 p.m.Chicago Midway
C$ 329
Delta
5 Feb
MDW9:33 a.m.Chicago Midway
5h 39m
1 stop
YYZ4:12 p.m.Toronto Pearson Intl
8 Feb
YYZ6:30 a.m.Toronto Pearson Intl
5h 35m
1 stop
MDW11:05 a.m.Chicago Midway
C$ 346
Delta
5 Feb
MDW1:26 p.m.Chicago Midway
4h 42m
1 stop
YYZ7:08 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$ 355

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Canada 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 15 January 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Canada that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Fri 6/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 265

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 6/2

11:05 a.m.-5:45 p.m.

1 stop5h 40m

Montreal Pierre Elliott Trudeau Intl

Sun 8/2

10:15 a.m.-3:20 p.m.

1 stop6h 05m

C$ 267

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 6/2

11:05 a.m.-5:45 p.m.

1 stop5h 40m

Montreal Pierre Elliott Trudeau Intl

Sun 8/2

10:15 a.m.-3:20 p.m.

1 stop6h 05m

C$ 269

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Tue 17/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 275

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 14/2

12:50 p.m.-3:32 p.m.

Nonstop1h 42m

Toronto Island

Wed 18/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

C$ 286

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Mon 23/2

3:24 p.m.-11:59 p.m.

1 stop10h 35m

Vancouver Intl

Wed 25/2

11:00 p.m.-4:16 p.m.

1 stop15h 16m

C$ 332

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/2

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

1 stop5h 39m

Toronto Pearson Intl

Sun 8/2

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

1 stop5h 35m

C$ 346

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/2

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

1 stop4h 42m

Toronto Pearson Intl

Sun 8/2

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

1 stop3h 52m

C$ 355

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 1/3

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

1 stop5h 09m

Toronto Pearson Intl

Sun 8/3

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

1 stop6h 39m

C$ 393

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 27/2

9:34 a.m.-4:10 p.m.

1 stop5h 36m

Toronto Pearson Intl

Fri 6/3

6:10 a.m.-8:54 a.m.

1 stop3h 44m

C$ 418

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 Canada from

How to get the cheapest flight ticket from Chicago Midway Airport to Canada

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 month to fly to Canada?

In general, March is the cheapest month to fly from Chicago Midway Airport to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 135. If you’re not able to fly to Canada in March, then July is your next best option. Flight prices from Chicago Midway Airport to Canada during July average around C$ 249.

What is the cheapest day to depart on your flight to Canada?

Our data shows that Tuesday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 307. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 454. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

What is the cheapest time of day to depart on your flight to Canada?

According to our data, the cheapest time of day to fly to Canada is in the morning. momondo users have found flights departing from Chicago Midway Airport to Canada in the morning for as low as C$ 335. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 466 per ticket.

What is the cheapest Chicago Midway to Canada flight route?

Fly from Chicago Midway to Toronto Island for the best Chicago Midway - Canada flight prices

What cabin class options are available on Chicago Midway to Canada flights?

There is only 1 cabin class available to choose from on Chicago Midway to Canada flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Canada flights?

You could potentially save up to 54% on your flight if you consider stops on a Chicago Midway Airport to Canada flight.

Cheap Chicago Midway Airport to Canada flight deals and tips

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

Best price found

C$ 477

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Canada

513 airports
The best flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is C$ 477
The fastest flight from Chicago Midway Airport to Canada takes 1h 40m
Direct flights go from Chicago Midway Airport to Canada every day.
There are 513 airports in Canada. From Chicago Midway Airport there are direct flights to Toronto Island (YTZ).
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Canada?

    Prices for flights from Chicago Midway Airport to Canada were last updated today.

  • How old do you have to be to fly from Chicago Midway Airport to Canada?

    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 Canada.

  • What documentation or ID do you need to fly to Canada?

    The necessary travel and health documents for your Canada trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Canada?

Why use momondo?

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

It is quick and easy to find Chicago to Canada flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Canada that suits you.

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

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

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

Once all potential Chicago to Canada flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Chicago to Canada flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Canada

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