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Cheap flights from Chicago Midway Airport to Canada from $79

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 12/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
12:45 pm - 3:27 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$187Porter Airlines
Find Deal
Sat, Nov 22 - Mon, Nov 24
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$188Porter Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
Multiple Airlines Logo
2:49 pm - 3:07 pmMDW-YWG
24h 18m1 stop
Multiple Airlines Logo
7:30 am - 9:52 amYWG-MDW
26h 22m1 stop
$192Multiple Airlines
Find Deal
Tue, Dec 9 - Sun, Dec 14
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$192Porter Airlines
Find Deal
Fri, Nov 28 - Thu, Dec 4
Multiple Airlines Logo
8:42 pm - 6:06 pmMDW-YWG
21h 24m2 stops
Multiple Airlines Logo
7:30 am - 10:12 pmYWG-MDW
14h 42m1 stop
$203Multiple Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
9:34 am - 2:48 pmMDW-YYZ
4h 14m1 stop
Delta Logo
3:38 pm - 6:00 pmYYZ-MDW
3h 22m1 stop
$233Delta
Find Deal
Fri, Dec 5 - Sun, Dec 7
Delta Logo
9:34 am - 3:57 pmMDW-YUL
5h 23m1 stop
Delta Logo
12:54 pm - 5:55 pmYUL-MDW
6h 01m1 stop
$236Delta
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Thu, Jan 29 - Wed, Feb 4
KLM Logo
9:34 am - 2:48 pmMDW-YYZ
4h 14m1 stop
KLM Logo
6:05 am - 12:34 pmYYZ-MDW
7h 29m1 stop
$283KLM
Find Deal
Fri, Dec 5 - Sun, Dec 7
WestJet Logo
7:16 pm - 3:53 pmMDW-YYZ
19h 37m2 stops
WestJet Logo
6:30 am - 11:05 amYYZ-MDW
5h 35m1 stop
$300WestJet
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Sun, Jan 11 - Sat, Jan 17
WestJet Logo
9:59 am - 4:15 pmMDW-YYZ
5h 16m1 stop
WestJet Logo
6:30 pm - 9:54 amYYZ-MDW
16h 24m2 stops
$301WestJet
Find Deal
Tue, Dec 2 - Thu, Dec 4

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets
Delta
Dec 5
MDW9:34 amChicago Midway
4h 14m
1 stop
YYZ2:48 pmToronto Pearson Intl
Dec 7
YYZ3:38 pmToronto Pearson Intl
3h 22m
1 stop
MDW6:00 pmChicago Midway
$233
Find similar
Delta
Jan 29
MDW9:34 amChicago Midway
5h 23m
1 stop
YUL3:57 pmMontreal Pierre Elliott Trudeau Intl
Feb 4
YUL12:54 pmMontreal Pierre Elliott Trudeau Intl
6h 01m
1 stop
MDW5:55 pmChicago Midway
$236
Find similar
Delta
Nov 23
MDW9:34 amChicago Midway
6h 41m
1 stop
YYZ5:15 pmToronto Pearson Intl
Dec 4
YYZ12:13 pmToronto Pearson Intl
6h 47m
1 stop
MDW6:00 pmChicago Midway
$250
Find similar

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets
WestJet
Jan 11
MDW7:16 pmChicago Midway
19h 37m
2 stops
YYZ3:53 pmToronto Pearson Intl
Jan 17
YYZ6:30 amToronto Pearson Intl
5h 35m
1 stop
MDW11:05 amChicago Midway
$300
Find similar
WestJet
Dec 2
MDW9:59 amChicago Midway
5h 16m
1 stop
YYZ4:15 pmToronto Pearson Intl
Dec 4
YYZ6:30 pmToronto Pearson Intl
16h 24m
2 stops
MDW9:54 amChicago Midway
$301
Find similar
WestJet
Nov 28
MDW7:02 pmChicago Midway
27h 19m
1 stop
YYZ11:21 pmToronto Pearson Intl
Dec 1
YYZ6:30 pmToronto Pearson Intl
16h 24m
2 stops
MDW9:54 amChicago Midway
$306
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 832,500 searches. Data last updated November 9, 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

Sat 11/22

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Mon 11/24

2:30 pm-3:20 pm

Nonstop1h 50m

$187

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 11/21

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/23

9:15 am-10:05 am

Nonstop1h 50m

$188

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 12/9

2:49 pm-3:07 pm

1 stop24h 18m

Winnipeg

Sun 12/14

7:30 am-9:52 am

1 stop26h 22m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 11/28

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Thu 12/4

2:30 pm-3:20 pm

Nonstop1h 50m

$192

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 12/8

8:42 pm-6:06 pm

2 stops21h 24m

Winnipeg

Fri 12/12

7:30 am-10:12 pm

1 stop14h 42m

$203

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 12/5

9:34 am-2:48 pm

1 stop4h 14m

Toronto Pearson Intl

Sun 12/7

3:38 pm-6:00 pm

1 stop3h 22m

$233

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 1/29

9:34 am-3:57 pm

1 stop5h 23m

Montreal Pierre Elliott Trudeau Intl

Wed 2/4

12:54 pm-5:55 pm

1 stop6h 01m

$236

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 12/5

9:34 am-2:48 pm

1 stop4h 14m

Toronto Pearson Intl

Sun 12/7

6:05 am-12:34 pm

1 stop7h 29m

$283

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 1/11

7:16 pm-3:53 pm

2 stops19h 37m

Toronto Pearson Intl

Sat 1/17

6:30 am-11:05 am

1 stop5h 35m

$300

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 12/2

9:59 am-4:15 pm

1 stop5h 16m

Toronto Pearson Intl

Thu 12/4

6:30 pm-9:54 am

2 stops16h 24m

$301

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?

If you aren’t able to travel during the month of July, then book flights to Canada from Chicago Midway Airport during August instead. Flights to Canada in August, while not as cheap as those in July, still average around $197.

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

Our data shows that Saturday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $253. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Canada for around $329.

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

In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Canada when you can find flight prices for as low as $270. Flying to Canada in the afternoon is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Canada is in the evening when prices are around $360.

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 are 3 cabin classes 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

$210

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 $210. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is $287.
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 are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Canada?

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 required travel and health documents for your Canada trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Canada. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Chicago Midway Airport to Canada

Compare and see reviews for airlines that fly from Chicago Midway Airport to Canada with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $185Free CancellationRating
8.0
388 reviews
Search Porter Airlines flights

Why use momondo?

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

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 Canada for you.

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

momondo does allow users to show only those flights to Canada from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Chicago to Canada flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Canada, momondo offers a useful price alert feature which will track prices for flights to Canada from Chicago and alert you when they change.

An easier way to manage your Canada 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.
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