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Cheap flights from Chicago Midway Airport to Canada from C$ 99

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 1/6. 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

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
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 296Porter Airlines
Wed, 13 May - Wed, 20 May
Porter Airlines Logo
10:30 a.m. - 1:10 p.m.
MDW
-
YTZ
1h 40mdirect
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 300Porter Airlines
Sat, 9 May - Sun, 10 May
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 301Porter Airlines
Wed, 15 Jul - Thu, 23 Jul
Multiple Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
Multiple Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
C$ 306Multiple Airlines
Thu, 14 May - Thu, 21 May
Delta Logo
2:12 p.m. - 11:10 p.m.
MDW
-
YYZ
7h 58m
1 stop
Delta Logo
6:10 a.m. - 8:47 a.m.
YYZ
-
MDW
3h 37m
1 stop
C$ 356Delta
Sat, 2 May - Tue, 5 May
Delta Logo
9:22 a.m. - 1:30 p.m.
MDW
-
YYZ
3h 08m
1 stop
Delta Logo
2:20 p.m. - 6:33 p.m.
YYZ
-
MDW
5h 13m
1 stop
C$ 368Delta
Thu, 7 May - Tue, 12 May
WestJet Logo
9:27 a.m. - 3:24 p.m.
MDW
-
YYZ
4h 57m
1 stop
WestJet Logo
4:09 p.m. - 6:38 p.m.
YYZ
-
MDW
3h 29m
1 stop
C$ 376WestJet
Sat, 9 May - Sun, 10 May
KLM Logo
6:36 p.m. - 10:59 p.m.
MDW
-
YYZ
3h 23m
1 stop
KLM Logo
2:20 p.m. - 6:33 p.m.
YYZ
-
MDW
5h 13m
1 stop
C$ 379KLM
Sat, 30 May - Sat, 6 Jun
WestJet Logo
9:22 a.m. - 5:29 p.m.
MDW
-
YYZ
7h 07m
1 stop
WestJet Logo
2:29 p.m. - 6:11 p.m.
YYZ
-
MDW
4h 42m
1 stop
C$ 389WestJet
Wed, 10 Jun - Sat, 13 Jun
Multiple Airlines Logo
12:24 p.m. - 10:45 a.m.
MDW
-
YVR
24h 21m
1 stop
Multiple Airlines Logo
8:25 p.m. - 11:09 a.m.
YVR
-
MDW
12h 44m
2 stops
C$ 443Multiple Airlines
Tue, 12 May - Tue, 19 May

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WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets
WestJet
9 May
MDW9:27 a.m.Chicago Midway
4h 57m
1 stop
YYZ3:24 p.m.Toronto Pearson Intl
10 May
YYZ4:09 p.m.Toronto Pearson Intl
3h 29m
1 stop
MDW6:38 p.m.Chicago Midway
C$ 376
WestJet
10 Jun
MDW9:22 a.m.Chicago Midway
7h 07m
1 stop
YYZ5:29 p.m.Toronto Pearson Intl
13 Jun
YYZ2:29 p.m.Toronto Pearson Intl
4h 42m
1 stop
MDW6:11 p.m.Chicago Midway
C$ 389
WestJet
28 May
MDW9:22 a.m.Chicago Midway
3h 08m
1 stop
YYZ1:30 p.m.Toronto Pearson Intl
31 May
YYZ6:10 a.m.Toronto Pearson Intl
3h 33m
1 stop
MDW8:43 a.m.Chicago Midway
C$ 587

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets
Delta
2 May
MDW2:12 p.m.Chicago Midway
7h 58m
1 stop
YYZ11:10 p.m.Toronto Pearson Intl
4 May
YYZ2:15 p.m.Toronto Pearson Intl
4h 43m
1 stop
MDW5:58 p.m.Chicago Midway
C$ 356
Delta
7 May
MDW9:22 a.m.Chicago Midway
3h 08m
1 stop
YYZ1:30 p.m.Toronto Pearson Intl
12 May
YYZ2:20 p.m.Toronto Pearson Intl
5h 13m
1 stop
MDW6:33 p.m.Chicago Midway
C$ 368
Delta
31 May
MDW9:22 a.m.Chicago Midway
6h 59m
1 stop
YYZ5:21 p.m.Toronto Pearson Intl
7 Jun
YYZ6:10 a.m.Toronto Pearson Intl
7h 26m
1 stop
MDW12:36 p.m.Chicago Midway
C$ 397

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 18 April 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

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 13/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Wed 20/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 296

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 9/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Sun 10/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 300

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Thu 23/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 301

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 14/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Thu 21/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 306

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 2/5

2:12 p.m.-11:10 p.m.

1 stop7h 58m

Toronto Pearson Intl

Tue 5/5

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

1 stop3h 37m

C$ 356

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 7/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

Toronto Pearson Intl

Tue 12/5

2:20 p.m.-6:33 p.m.

1 stop5h 13m

C$ 368

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 9/5

9:27 a.m.-3:24 p.m.

1 stop4h 57m

Toronto Pearson Intl

Sun 10/5

4:09 p.m.-6:38 p.m.

1 stop3h 29m

C$ 376

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 30/5

6:36 p.m.-10:59 p.m.

1 stop3h 23m

Toronto Pearson Intl

Sat 6/6

2:20 p.m.-6:33 p.m.

1 stop5h 13m

C$ 379

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 10/6

9:22 a.m.-5:29 p.m.

1 stop7h 07m

Toronto Pearson Intl

Sat 13/6

2:29 p.m.-6:11 p.m.

1 stop4h 42m

C$ 389

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Tue 12/5

12:24 p.m.-10:45 a.m.

1 stop24h 21m

Vancouver Intl

Tue 19/5

8:25 p.m.-11:09 a.m.

2 stops12h 44m

C$ 443

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$ 248. If you’re not able to fly to Canada in July, then January is your next best option. Flight prices from Chicago Midway Airport to Canada during January average around C$ 256.

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

Our data shows that Friday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 313. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 410. 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$ 348. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 374 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Canada.

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$ 133

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Canada

513 airports
The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is C$ 133. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is C$ 306.
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

Frequently asked questions about flying from Chicago Midway Airport to Canada

  • 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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