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Cheap flights from Chicago Midway Airport to Canada from $68

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 9/9. 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

Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$164Porter Airlines
Find Deal
Thu, Sep 11 - Mon, Sep 15
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$165Porter Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$184Air Transat
Find Deal
Wed, Sep 10 - Fri, Sep 12
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$188
Find Deal
Fri, Sep 12 - Fri, Sep 19
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$189
Find Deal
Thu, Sep 4 - Mon, Sep 8
Delta Logo
9:30 am - 5:23 pmMDW-YYZ
6h 53m1 stop
Delta Logo
6:00 am - 1:03 pmYYZ-MDW
8h 03m1 stop
$233Delta
Find Deal
Wed, Sep 10 - Sat, Sep 13
Delta Logo
9:35 am - 5:19 pmMDW-YYZ
6h 44m1 stop
Delta Logo
4:12 pm - 6:35 pmYYZ-MDW
3h 23m1 stop
$234Delta
Find Deal
Sat, Sep 13 - Tue, Sep 16
Air Transat Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Air Transat Logo
9:00 am - 9:50 amYTZ-MDW
1h 50mnonstop
$235Air Transat
Find Deal
Thu, Aug 28 - Mon, Sep 1
WestJet Logo
12:43 pm - 9:58 pmMDW-YYZ
8h 15m1 stop
WestJet Logo
11:33 am - 9:44 pmYYZ-MDW
11h 11m1 stop
$304WestJet
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Thu, Aug 21 - Fri, Aug 22
WestJet Logo
9:20 am - 6:28 pmMDW-YYZ
8h 08m1 stop
WestJet Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
$312WestJet
Find Deal
Wed, Oct 1 - Mon, Oct 6

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets
WestJet
Aug 21
MDW12:43 pmChicago Midway
8h 15m
1 stop
YYZ9:58 pmToronto Pearson Intl
Aug 22
YYZ11:33 amToronto Pearson Intl
11h 11m
1 stop
MDW9:44 pmChicago Midway
$304
Find similar
WestJet
Oct 1
MDW9:20 amChicago Midway
8h 08m
1 stop
YYZ6:28 pmToronto Pearson Intl
Oct 6
YYZ6:00 pmToronto Pearson Intl
5h 14m
1 stop
MDW10:14 pmChicago Midway
$312
Find similar
WestJet
Aug 21
MDW12:43 pmChicago Midway
8h 15m
1 stop
YYZ9:58 pmToronto Pearson Intl
Aug 24
YYZ6:07 pmToronto Pearson Intl
16h 29m
1 stop
MDW9:36 amChicago Midway
$319
Find similar

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets
Delta
Sep 10
MDW9:30 amChicago Midway
6h 53m
1 stop
YYZ5:23 pmToronto Pearson Intl
Sep 13
YYZ6:00 amToronto Pearson Intl
8h 03m
1 stop
MDW1:03 pmChicago Midway
$233
Find similar
Delta
Sep 13
MDW9:35 amChicago Midway
6h 44m
1 stop
YYZ5:19 pmToronto Pearson Intl
Sep 16
YYZ4:12 pmToronto Pearson Intl
3h 23m
1 stop
MDW6:35 pmChicago Midway
$234
Find similar
Delta
Sep 20
MDW1:43 pmChicago Midway
8h 35m
1 stop
YUL11:18 pmMontreal Pierre Elliott Trudeau Intl
Sep 23
YUL12:47 pmMontreal Pierre Elliott Trudeau Intl
9h 49m
1 stop
MDW9:36 pmChicago Midway
$237
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 July 31, 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

Thu 9/11

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Mon 9/15

7:50 am-8:39 am

Nonstop1h 49m

$164

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/7

7:50 am-8:39 am

Nonstop1h 49m

$165

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/10

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Fri 9/12

3:35 pm-4:24 pm

Nonstop1h 49m

$184

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/12

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Fri 9/19

7:50 am-8:39 am

Nonstop1h 49m

$188

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Mon 9/8

7:50 am-8:39 am

Nonstop1h 49m

$189

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 9/10

9:30 am-5:23 pm

1 stop6h 53m

Toronto Pearson Intl

Sat 9/13

6:00 am-1:03 pm

1 stop8h 03m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 9/13

9:35 am-5:19 pm

1 stop6h 44m

Toronto Pearson Intl

Tue 9/16

4:12 pm-6:35 pm

1 stop3h 23m

$234

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 8/28

9:40 am-12:20 pm

Nonstop1h 40m

Toronto Island

Mon 9/1

9:00 am-9:50 am

Nonstop1h 50m

$235

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 8/21

12:43 pm-9:58 pm

1 stop8h 15m

Toronto Pearson Intl

Fri 8/22

11:33 am-9:44 pm

1 stop11h 11m

$304

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 10/1

9:20 am-6:28 pm

1 stop8h 08m

Toronto Pearson Intl

Mon 10/6

6:00 pm-10:14 pm

1 stop5h 14m

$312

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 May instead. Flights to Canada in May, while not as cheap as those in July, still average around $216.

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

Our data shows that Thursday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $272. 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 $367.

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 $278. 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

$68

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Canada

4 airports
The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is $68. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is $164.
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 4 airports near Canada: Montreal Pierre Elliott Trudeau Intl (YUL), Calgary (YYC), Toronto Pearson Intl (YYZ), Toronto Island (YTZ)
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  • 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 $187Free CancellationRating
8.0
318 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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