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Cheap flights from Chicago Midway Airport to Canada from $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 1/18. 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

These are some of the best round-trip flight deals from Chicago Midway Airport to Canada that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Canada.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Canada? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Canada, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Canada

Find recent round-trip train or bus tickets from Chicago Midway Airport to Canada.

All round-trip flight deals to Canada

The cheapest plane tickets to Canada found on KAYAK recently.
11:19 am - 8:53 pmMDW-YYC
10h 34m1 stop
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
$249Delta
Find Deal
Sa, Jän 18 - Sa, Jän 25
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
$258Delta
Find Deal
Sa, Jän 18 - Fr, Jän 24
6:15 am - 11:53 pmMDW-YYZ
16h 38m2 stops
7:00 am - 3:02 pmYYZ-MDW
9h 02m1 stop
Mo, Feb 3 - Mo, Feb 10
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$262Porter Airlines
Find Deal
Do, Feb 13 - So, Feb 16
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$263Porter Airlines
Find Deal
Do, Feb 13 - So, Feb 16
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
8:00 am - 5:47 pmYYC-MDW
8h 47m2 stops
$263Delta
Find Deal
Sa, Jän 18 - Sa, Jän 25
12:43 pm - 10:30 pmMDW-YVR
11h 47m1 stop
8:35 pm - 4:16 pmYVR-MDW
17h 41m2 stops
Mo, Feb 3 - Mo, Feb 10
1:26 pm - 11:11 pmMDW-YYZ
8h 45m1 stop
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
$398WestJet
Find Deal
Di, Jän 28 - Mi, Jän 29
1:26 pm - 11:11 pmMDW-YYZ
8h 45m1 stop
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
$404WestJet
Find Deal
Fr, Jän 31 - So, Feb 2
2:08 pm - 12:30 amMDW-YEG
11h 22m2 stops
9:45 am - 10:20 pmYEG-MDW
11h 35m2 stops
$613KLM
Find Deal
Do, Feb 6 - Do, Feb 13
11:19 am - 8:53 pmMDW-YYC
10h 34m1 stop
$99Delta
Find Deal
Sa, Jän 18
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$102Delta
Find Deal
Sa, Jän 18
8:15 am - 10:30 pmMDW-YVR
16h 15m2 stops
Mi, Jän 8
8:15 am - 10:30 pmMDW-YVR
16h 15m2 stops
Mi, Jän 8
1:05 pm - 8:15 pmMDW-YHZ
5h 10m1 stop
$128Porter Airlines
Find Deal
So, Feb 16
1:05 pm - 10:25 pmMDW-YHZ
7h 20m2 stops
$129Porter Airlines
Find Deal
Mi, Feb 5
10:19 am - 11:11 pmMDW-YYZ
11h 52m1 stop
$185WestJet
Find Deal
Do, Jän 16
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$188Air Transat
Find Deal
Fr, Feb 21
9:20 am - 6:23 pmMDW-YYZ
8h 03m1 stop
$192WestJet
Find Deal
Di, Mai 27
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$257Air Transat
Find Deal
Fr, Jän 3
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$434Porter Airlines
Find Deal
Fr, Dez 27 - Mo, Jän 13
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$441Porter Airlines
Find Deal
Sa, Dez 28 - Mo, Jän 6
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
Sa, Dez 28 - Mo, Jän 6
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$491Porter Airlines
Find Deal
Mi, Dez 25 - Mi, Jän 1
5:04 pm - 11:08 pmMDW-YYZ
5h 04m1 stop
7:10 am - 2:33 pmYYZ-MDW
8h 23m1 stop
Do, Dez 26 - Fr, Jän 10
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
$556Air Transat
Find Deal
Sa, Dez 28 - Sa, Jän 4
5:04 pm - 11:08 pmMDW-YYZ
5h 04m1 stop
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
$600WestJet
Find Deal
Fr, Dez 27 - Mo, Jän 13
11:48 am - 9:07 pmMDW-YYC
10h 19m1 stop
7:00 am - 5:44 pmYYC-MDW
9h 44m1 stop
$625Delta
Find Deal
Di, Dez 24 - Fr, Dez 27
9:30 am - 9:07 pmMDW-YYC
12h 37m2 stops
7:00 am - 5:44 pmYYC-MDW
9h 44m1 stop
$634Delta
Find Deal
Di, Dez 24 - Fr, Dez 27
4:50 pm - 11:08 pmMDW-YYZ
5h 18m1 stop
6:30 am - 11:08 amYYZ-MDW
5h 38m1 stop
$636WestJet
Find Deal
Mi, Dez 25 - Mi, Jän 1
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$262Porter Airlines
Find Deal
Do, Feb 13 - So, Feb 16
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$263Porter Airlines
Find Deal
Do, Feb 13 - So, Feb 16
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$264Porter Airlines
Find Deal
Fr, Feb 14 - Mo, Feb 17
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$265Porter Airlines
Find Deal
Fr, Feb 14 - Di, Feb 18
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$266Porter Airlines
Find Deal
Do, Feb 13 - So, Feb 16
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$270Porter Airlines
Find Deal
Do, Feb 13 - So, Feb 16
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
Do, Feb 13 - So, Feb 16
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$619Air Transat
Find Deal
Fr, Mai 23 - Mi, Mai 28
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$620Air Transat
Find Deal
Do, Jun 19 - Do, Jun 26
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$680Air Transat
Find Deal
Mi, Feb 12 - Mi, Feb 19

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets
WestJet
Jan 28
MDW1:26 pmChicago Midway
8h 45m
1 stop
YYZ11:11 pmToronto Pearson Intl
Jan 29
YYZ6:30 amToronto Pearson Intl
7h 16m
1 stop
MDW12:46 pmChicago Midway
WestJet
Jan 31
MDW1:26 pmChicago Midway
8h 45m
1 stop
YYZ11:11 pmToronto Pearson Intl
Feb 2
YYZ6:30 amToronto Pearson Intl
7h 16m
1 stop
MDW12:46 pmChicago Midway
WestJet
Apr 16
MDW9:20 amChicago Midway
8h 03m
1 stop
YYZ6:23 pmToronto Pearson Intl
Apr 20
YYZ6:30 amToronto Pearson Intl
7h 35m
1 stop
MDW1:05 pmChicago Midway

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets
Delta
Jan 18
MDW11:19 amChicago Midway
10h 34m
1 stop
YYC8:53 pmCalgary
Jan 25
YYC6:35 amCalgary
10h 12m
1 stop
MDW5:47 pmChicago Midway
Delta
Jan 18
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
Jan 24
YYC6:35 amCalgary
10h 12m
1 stop
MDW5:47 pmChicago Midway
Delta
Jan 18
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
Jan 24
YYC6:35 amCalgary
10h 39m
2 stops
MDW6:14 pmChicago Midway

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 February, then book flights to Canada from Chicago Midway Airport during July instead. Flights to Canada in July, while not as cheap as those in February, still average around $245.

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

Our data shows that Monday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $245. 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 $314.

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

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Canada when you can find flight prices for as low as $268. Flying to Canada in the morning 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 29% 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

$99

Fastest flight time

1h 42m

Direct flights

Every day

Airports in Canada

7 airports
The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is $99. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is $249.
The fastest flight from Chicago Midway Airport to Canada takes 1h 42m
Direct flights go from Chicago Midway Airport to Canada every day.
There are 7 airports near Canada: Ottawa (YOW), Calgary (YYC), Vancouver Intl (YVR), Edmonton (YEG), Halifax Intl (YHZ), Toronto Pearson Intl (YYZ), Toronto Island (YTZ)

  • 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 $218Free CancellationRating
7.9
282 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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Popular cities in Canada

Popular flights according to clicks in the last 7 days on momondo