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Cheap flights from Canada to Chicago Midway Airport from $133

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Canada to Chicago Midway Airport departing on 12/14. 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 Canada to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Canada to Chicago 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 Canada to Chicago.

Cheap last minute flights

Planning a quick getaway from Canada to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
6:35 am - 6:14 pmYYC-MDW
10h 39m2 stops
1:26 pm - 8:53 pmMDW-YYC
8h 27m1 stop
$221Delta
Find Deal
Wed, Jan 8 - Mon, Jan 13
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$236Delta
Find Deal
Thu, Jan 9 - Tue, Jan 14
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$255Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$261Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
6:30 am - 6:32 pmYYZ-MDW
13h 02m1 stop
9:38 am - 11:34 pmMDW-YYZ
12h 56m1 stop
$267WestJet
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
11:19 am - 11:11 pmMDW-YYZ
10h 52m1 stop
$271WestJet
Find Deal
Tue, Jan 7 - Sat, Jan 11
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$133Porter Airlines
Find Deal
Sat, Dec 14
6:35 am - 6:14 pmYYC-MDW
10h 39m2 stops
$136Delta
Find Deal
Wed, Jan 8
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$136Porter Airlines
Find Deal
Sat, Dec 14
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$138Porter Airlines
Find Deal
Thu, Dec 12
7:30 am - 5:50 pmYWG-MDW
10h 20m1 stop
Fri, Jan 10
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$170Air Transat
Find Deal
Mon, Jan 6
12:45 pm - 6:00 pmYUL-MDW
6h 15m1 stop
$171WestJet
Find Deal
Sat, Apr 19
12:25 pm - 10:06 pmYYZ-MDW
10h 41m1 stop
$174WestJet
Find Deal
Sat, Dec 14
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$203Air Transat
Find Deal
Sat, Dec 21
12:21 pm - 9:46 pmYYZ-MDW
10h 25m1 stop
$303Undisclosed Carrier
Find Deal
Fri, Nov 29
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$375Porter Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 9
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$379Air Transat
Find Deal
Tue, Nov 26 - Thu, Jan 16
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$400Porter Airlines
Find Deal
Tue, Nov 26 - Fri, Dec 6
2:55 pm - 6:32 pmYYZ-MDW
4h 37m1 stop
9:30 am - 11:41 pmMDW-YYZ
13h 11m1 stop
$405WestJet
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:00 am - 6:32 pmYUL-MDW
13h 32m1 stop
2:17 pm - 11:33 pmMDW-YUL
8h 16m1 stop
$406WestJet
Find Deal
Sun, Nov 24 - Wed, Nov 27
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$412Air Transat
Find Deal
Tue, Nov 26 - Wed, Dec 4
8:00 pm - 7:55 amYYZ-MDW
12h 55m1 stop
12:43 pm - 7:06 pmMDW-YYZ
5h 23m1 stop
Sun, Nov 24 - Tue, Dec 3
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
Mon, Nov 25 - Sat, Nov 30
6:00 am - 12:49 pmYYZ-MDW
7h 49m1 stop
2:17 pm - 11:34 pmMDW-YYZ
8h 17m1 stop
$513Delta
Find Deal
Mon, Nov 25 - Sun, Dec 1
7:10 am - 12:49 pmYUL-MDW
6h 39m1 stop
1:30 pm - 11:11 pmMDW-YUL
8h 41m1 stop
$521Delta
Find Deal
Sat, Nov 23 - Tue, Nov 26
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$237Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$239Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$255Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$262Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$271Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
Wed, Dec 18 - Sun, Jan 5

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets
Porter Airlines
Dec 12
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 15
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Dec 13
YTZ10:20 amToronto Island
1h 50m
MDW11:10 amChicago Midway
Dec 17
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Dec 12
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 16
MDW12:05 pmChicago Midway
1h 42m
YTZ2:47 pmToronto Island

WestJet flights from Canada to Chicago Midway Airport

Our best WestJet deals on Canada to Chicago Midway Airport flight tickets
WestJet
Dec 12
YYZ6:30 amToronto Pearson Intl
13h 02m
1 stop
MDW6:32 pmChicago Midway
Dec 16
MDW9:38 amChicago Midway
12h 56m
1 stop
YYZ11:34 pmToronto Pearson Intl
WestJet
Jan 7
YYZ6:30 amToronto Pearson Intl
7h 16m
1 stop
MDW12:46 pmChicago Midway
Jan 11
MDW11:19 amChicago Midway
10h 52m
1 stop
YYZ11:11 pmToronto Pearson Intl
WestJet
Apr 12
YYZ6:30 amToronto Pearson Intl
7h 50m
1 stop
MDW1:20 pmChicago Midway
Apr 21
MDW9:20 amChicago Midway
8h 03m
1 stop
YYZ6:23 pmToronto Pearson Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Canada to Chicago Midway Airport

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 Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Canada, with most prices found around $211. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Canada during the month March is also very affordable. Most momondo users find prices during this month for around $219.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Canada. The lowest ticket price found for a Wednesday departure recently was $228. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $385.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Canada at noon is the least expensive time of day to depart. momondo users have found prices as low as $203 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $258. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Canada to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Canada - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

We recommend purchasing flights from Canada to Chicago Midway Airport 24 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $260. In the past 72 hours, momondo users found flights from Canada to Chicago Midway Airport for as low as $170.

What cabin class options are available on Canada to Chicago Midway flights?

There are 3 cabin classes available to choose from on Canada to Chicago Midway 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 Canada to Chicago Midway Airport flights?

You could potentially save up to 1% on your flight if you consider stops on a Canada to Chicago Midway Airport flight.

Cheap Canada to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago Midway Airport

Best Price Found

$133

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Canada in the past 72 hours is $133. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is $219.
The fastest flight from Canada to Chicago Midway Airport takes 1h 50m
Direct flights go from Canada to Chicago Midway Airport every day.

  • When did momondo last update prices for flights from Canada to Chicago Midway Airport?

    Prices for flights from Canada to Chicago Midway Airport were last updated today.

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

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

    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 Canada to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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


Best airlines flying from Canada to Chicago Midway Airport

Compare and see reviews for airlines that fly from Canada to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $205Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Canada.

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

Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Canada.

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

Yes. momondo can track prices for Canada to Chicago 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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