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Cheap flights from Chicago Midway Airport to Canada from $70

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 10/15. 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 - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$171Porter Airlines
Find Deal
Sat, Oct 18 - Thu, Oct 23
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$173Porter Airlines
Find Deal
Mon, Oct 20 - Thu, Oct 23
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$175Porter Airlines
Find Deal
Mon, Oct 6 - Fri, Oct 17
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$177Porter Airlines
Find Deal
Sun, Oct 12 - Thu, Oct 16
Multiple Airlines Logo
2:06 pm - 11:12 amMDW-YVR
23h 06m1 stop
Multiple Airlines Logo
7:45 pm - 12:41 pmYVR-MDW
14h 56m2 stops
$203Multiple Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
Multiple Airlines Logo
8:05 am - 8:48 pmMDW-YVR
14h 43m1 stop
Multiple Airlines Logo
8:30 pm - 8:21 pmYVR-MDW
21h 51m2 stops
$206Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Delta Logo
1:43 pm - 8:42 pmMDW-YYC
7h 59m1 stop
Delta Logo
6:40 am - 5:35 pmYYC-MDW
9h 55m1 stop
$251Delta
Find Deal
Tue, Sep 30 - Fri, Oct 3
Delta Logo
9:20 am - 1:54 pmMDW-YYC
5h 34m1 stop
Delta Logo
6:20 am - 6:08 pmYYC-MDW
10h 48m2 stops
$261Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
WestJet Logo
9:20 am - 3:59 pmMDW-YYZ
5h 39m1 stop
WestJet Logo
6:20 am - 1:08 pmYYZ-MDW
7h 48m1 stop
$277WestJet
Find Deal
Sat, Nov 1 - Sat, Nov 8
WestJet Logo
10:35 am - 4:50 pmMDW-YYZ
5h 15m1 stop
WestJet Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
$289WestJet
Find Deal
Sat, Oct 18 - Sun, Oct 19

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets
WestJet
Nov 1
MDW9:20 amChicago Midway
5h 39m
1 stop
YYZ3:59 pmToronto Pearson Intl
Nov 8
YYZ6:20 amToronto Pearson Intl
7h 48m
1 stop
MDW1:08 pmChicago Midway
$277
Find similar
WestJet
Oct 18
MDW10:35 amChicago Midway
5h 15m
1 stop
YYZ4:50 pmToronto Pearson Intl
Oct 19
YYZ6:00 pmToronto Pearson Intl
5h 14m
1 stop
MDW10:14 pmChicago Midway
$289
Find similar
WestJet
Oct 14
MDW9:20 amChicago Midway
19h 53m
2 stops
YYZ6:13 amToronto Pearson Intl
Oct 16
YYZ7:24 pmToronto Pearson Intl
23h 19m
1 stop
MDW5:43 pmChicago Midway
$292
Find similar

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets
Delta
Sep 30
MDW1:43 pmChicago Midway
7h 59m
1 stop
YYC8:42 pmCalgary
Oct 3
YYC6:40 amCalgary
9h 55m
1 stop
MDW5:35 pmChicago Midway
$251
Find similar
Delta
Nov 8
MDW9:20 amChicago Midway
5h 34m
1 stop
YYC1:54 pmCalgary
Nov 15
YYC6:20 amCalgary
10h 48m
2 stops
MDW6:08 pmChicago Midway
$261
Find similar
Delta
Nov 8
MDW9:20 amChicago Midway
5h 34m
1 stop
YYC1:54 pmCalgary
Nov 15
YYC6:20 amCalgary
5h 47m
1 stop
MDW1:07 pmChicago Midway
$262
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 September 17, 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

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sat 10/18

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Thu 10/23

11:00 am-4:24 pm

1 stop6h 24m

$171

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Mon 10/20

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Thu 10/23

11:00 am-4:24 pm

1 stop6h 24m

$173

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Mon 10/6

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Fri 10/17

11:00 am-4:24 pm

1 stop6h 24m

$175

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sun 10/12

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Thu 10/16

11:00 am-4:24 pm

1 stop6h 24m

$177

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Wed 11/12

2:06 pm-11:12 am

1 stop23h 06m

Vancouver Intl

Tue 11/18

7:45 pm-12:41 pm

2 stops14h 56m

$203

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Wed 10/15

8:05 am-8:48 pm

1 stop14h 43m

Vancouver Intl

Wed 10/22

8:30 pm-8:21 pm

2 stops21h 51m

$206

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 9/30

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

Fri 10/3

6:40 am-5:35 pm

1 stop9h 55m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

9:20 am-1:54 pm

1 stop5h 34m

Calgary

Sat 11/15

6:20 am-6:08 pm

2 stops10h 48m

$261

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 11/1

9:20 am-3:59 pm

1 stop5h 39m

Toronto Pearson Intl

Sat 11/8

6:20 am-1:08 pm

1 stop7h 48m

$277

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 10/18

10:35 am-4:50 pm

1 stop5h 15m

Toronto Pearson Intl

Sun 10/19

6:00 pm-10:14 pm

1 stop5h 14m

$289

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 $263. 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 $334.

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 $273. 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?

You could potentially save up to 4% 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

$88

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 $88. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is $196.
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 $187Free CancellationRating
7.9
365 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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Find better results for your trip to Canada

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