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Cheap flights from Chicago Midway Airport to Canada from C$ 121

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 24/11. 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 Canada

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 263Porter Airlines
Find Deal
Sun, 23 Nov - Mon, 24 Nov
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 270Porter Airlines
Find Deal
Fri, 28 Nov - Mon, 1 Dec
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
Find Deal
Mon, 24 Nov - Tue, 2 Dec
Multiple Airlines Logo
6:15 a.m. - 10:45 p.m.MDW-YVR
18h 30m2 stops
Multiple Airlines Logo
11:00 p.m. - 8:46 a.m.YVR-MDW
31h 46m1 stop
C$ 309Multiple Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Delta Logo
9:34 a.m. - 2:48 p.m.MDW-YYZ
4h 14m1 stop
Delta Logo
6:05 a.m. - 12:34 p.m.YYZ-MDW
7h 29m1 stop
C$ 327Delta
Find Deal
Fri, 5 Dec - Sun, 7 Dec
Multiple Airlines Logo
8:42 p.m. - 11:12 a.m.MDW-YVR
16h 30m1 stop
Multiple Airlines Logo
9:15 p.m. - 9:22 p.m.YVR-MDW
22h 07m2 stops
C$ 330Multiple Airlines
Find Deal
Fri, 5 Dec - Fri, 12 Dec
Delta Logo
9:34 a.m. - 3:57 p.m.MDW-YUL
5h 23m1 stop
Delta Logo
12:54 p.m. - 5:55 p.m.YUL-MDW
6h 01m1 stop
C$ 331Delta
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Thu, 29 Jan - Sun, 1 Feb
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$ 397KLM
Find Deal
Fri, 5 Dec - Sun, 7 Dec
WestJet Logo
7:16 p.m. - 3:53 p.m.MDW-YYZ
19h 37m2 stops
WestJet Logo
6:30 a.m. - 11:05 a.m.YYZ-MDW
5h 35m1 stop
C$ 421WestJet
Find Deal
Sun, 11 Jan - Sat, 17 Jan
WestJet Logo
10:49 a.m. - 5:02 p.m.MDW-YYZ
5h 13m1 stop
WestJet Logo
6:12 p.m. - 9:54 a.m.YYZ-MDW
16h 42m1 stop
C$ 423WestJet
Find Deal
Mon, 8 Dec - Mon, 15 Dec

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets
Delta
5 Dec
MDW9:34 a.m.Chicago Midway
4h 14m
1 stop
YYZ2:48 p.m.Toronto Pearson Intl
7 Dec
YYZ6:05 a.m.Toronto Pearson Intl
7h 29m
1 stop
MDW12:34 p.m.Chicago Midway
C$ 327
Find similar
Delta
29 Jan
MDW9:34 a.m.Chicago Midway
5h 23m
1 stop
YUL3:57 p.m.Montreal Pierre Elliott Trudeau Intl
1 Feb
YUL12:54 p.m.Montreal Pierre Elliott Trudeau Intl
6h 01m
1 stop
MDW5:55 p.m.Chicago Midway
C$ 331
Find similar
Delta
23 Nov
MDW9:34 a.m.Chicago Midway
6h 41m
1 stop
YYZ5:15 p.m.Toronto Pearson Intl
4 Dec
YYZ12:13 p.m.Toronto Pearson Intl
6h 47m
1 stop
MDW6:00 p.m.Chicago Midway
C$ 351
Find similar

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets
WestJet
11 Jan
MDW7:16 p.m.Chicago Midway
19h 37m
2 stops
YYZ3:53 p.m.Toronto Pearson Intl
17 Jan
YYZ6:30 a.m.Toronto Pearson Intl
5h 35m
1 stop
MDW11:05 a.m.Chicago Midway
C$ 421
Find similar
WestJet
8 Dec
MDW10:49 a.m.Chicago Midway
5h 13m
1 stop
YYZ5:02 p.m.Toronto Pearson Intl
15 Dec
YYZ6:12 p.m.Toronto Pearson Intl
16h 42m
1 stop
MDW9:54 a.m.Chicago Midway
C$ 423
Find similar
WestJet
24 Dec
MDW5:59 p.m.Chicago Midway
28h 40m
2 stops
YYZ11:39 p.m.Toronto Pearson Intl
31 Dec
YYZ6:00 a.m.Toronto Pearson Intl
6h 06m
1 stop
MDW11:06 a.m.Chicago Midway
C$ 430
Find similar

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 10 November 2025.
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

Sun 23/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

Toronto Island

Mon 24/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 28/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

Toronto Island

Mon 1/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 270

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 24/11

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

Nonstop1h 42m

Toronto Island

Tue 2/12

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

Nonstop1h 50m

C$ 275

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Thu 4/12

6:15 a.m.-10:45 p.m.

2 stops18h 30m

Vancouver Intl

Sun 7/12

11:00 p.m.-8:46 a.m.

1 stop31h 46m

C$ 309

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 5/12

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$ 327

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Fri 5/12

8:42 p.m.-11:12 a.m.

1 stop16h 30m

Vancouver Intl

Fri 12/12

9:15 p.m.-9:22 p.m.

2 stops22h 07m

C$ 330

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 29/1

9:34 a.m.-3:57 p.m.

1 stop5h 23m

Montreal Pierre Elliott Trudeau Intl

Sun 1/2

12:54 p.m.-5:55 p.m.

1 stop6h 01m

C$ 331

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 5/12

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$ 397

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 11/1

7:16 p.m.-3:53 p.m.

2 stops19h 37m

Toronto Pearson Intl

Sat 17/1

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

1 stop5h 35m

C$ 421

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 8/12

10:49 a.m.-5:02 p.m.

1 stop5h 13m

Toronto Pearson Intl

Mon 15/12

6:12 p.m.-9:54 a.m.

1 stop16h 42m

C$ 423

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, July 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$ 251. If you’re not able to fly to Canada in July, then August is your next best option. Flight prices from Chicago Midway Airport to Canada during August average around C$ 277.

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$ 311. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 460. 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$ 363. 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$ 476 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 5% 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$ 192

Fastest flight time

1h 42m

Direct flights

Every day

Airports in Canada

1 airport
The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is C$ 192. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is C$ 404.
The fastest flight from Chicago Midway Airport to Canada takes 1h 42m
Direct flights go from Chicago Midway Airport to Canada every day.
There is 1 airport near Canada: 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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