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Cheap flights from Canada to Chicago from $112

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 departing on 11/26. 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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0 bags

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Find the cheapest flights from Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Multiple Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$187Multiple Airlines
Find Deal
Fri, Jan 16 - Sun, Jan 25
Porter Airlines Logo
11:00 am - 11:50 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
12:45 pm - 3:27 pmMDW-YTZ
1h 42mnonstop
$189Porter Airlines
Find Deal
Sat, Feb 28 - Sat, Mar 7
Porter Airlines Logo
11:00 am - 11:50 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$191Porter Airlines
Find Deal
Sat, Feb 28 - Sun, Mar 8
Delta Logo
12:13 pm - 6:00 pmYYZ-MDW
6h 47m1 stop
Delta Logo
6:40 pm - 11:11 pmMDW-YYZ
3h 31m1 stop
$201Delta
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
12:13 pm - 6:00 pmYYZ-MDW
6h 47m1 stop
Delta Logo
6:40 pm - 11:11 pmMDW-YYZ
3h 31m1 stop
$210Delta
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
6:05 am - 12:34 pmYYZ-MDW
7h 29m1 stop
Delta Logo
9:34 am - 5:15 pmMDW-YYZ
6h 41m1 stop
$211Delta
Find Deal
Fri, Nov 21 - Thu, Nov 27
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$217Air Transat
Find Deal
Fri, Mar 13 - Mon, Mar 23
Air Transat Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$253Air Transat
Find Deal
Tue, Nov 11 - Tue, Nov 18
WestJet Logo
6:00 am - 11:06 amYYZ-MDW
6h 06m1 stop
WestJet Logo
11:48 am - 11:20 pmMDW-YYZ
10h 32m1 stop
$264WestJet
Find Deal
Fri, Dec 26 - Mon, Dec 29
WestJet Logo
6:00 am - 11:06 amYYZ-MDW
6h 06m1 stop
WestJet Logo
11:48 am - 11:20 pmMDW-YYZ
10h 32m1 stop
$266WestJet
Find Deal
Tue, Dec 23 - Sat, Dec 27

Delta flights from Canada to Chicago Midway Airport

Our best Delta deals on Canada to Chicago Midway Airport flight tickets
Delta
Dec 4
YYZ12:13 pmToronto Pearson Intl
6h 47m
1 stop
MDW6:00 pmChicago Midway
Dec 8
MDW6:40 pmChicago Midway
3h 31m
1 stop
YYZ11:11 pmToronto Pearson Intl
$201
Find similar
Delta
Dec 4
YYZ12:13 pmToronto Pearson Intl
6h 47m
1 stop
MDW6:00 pmChicago Midway
Dec 8
MDW6:40 pmChicago Midway
3h 31m
1 stop
YYZ11:11 pmToronto Pearson Intl
$210
Find similar
Delta
Nov 21
YYZ6:05 amToronto Pearson Intl
7h 29m
1 stop
MDW12:34 pmChicago Midway
Nov 27
MDW9:34 amChicago Midway
6h 41m
1 stop
YYZ5:15 pmToronto Pearson Intl
$211
Find similar

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets
Porter Airlines
Feb 28
YTZ11:00 amToronto Island
1h 50m
MDW11:50 amChicago Midway
Mar 7
MDW12:45 pmChicago Midway
1h 42m
YTZ3:27 pmToronto Island
$189
Find similar
Porter Airlines
Feb 28
YTZ11:00 amToronto Island
1h 50m
MDW11:50 amChicago Midway
Mar 8
MDW4:15 pmChicago Midway
1h 42m
YTZ6:57 pmToronto Island
$191
Find similar
Porter Airlines
Feb 25
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
Mar 7
MDW12:45 pmChicago Midway
1h 42m
YTZ3:27 pmToronto Island
$192
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Canada to Chicago Midway Airport 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 October 23, 2025.
Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 1/25

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/28

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Sat 3/7

12:45 pm-3:27 pm

Nonstop1h 42m

$189

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/28

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Sun 3/8

4:15 pm-6:57 pm

Nonstop1h 42m

$191

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/4

12:13 pm-6:00 pm

1 stop6h 47m

Chicago Midway

Mon 12/8

6:40 pm-11:11 pm

1 stop3h 31m

$201

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/4

12:13 pm-6:00 pm

1 stop6h 47m

Chicago Midway

Mon 12/8

6:40 pm-11:11 pm

1 stop3h 31m

$210

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 11/21

6:05 am-12:34 pm

1 stop7h 29m

Chicago Midway

Thu 11/27

9:34 am-5:15 pm

1 stop6h 41m

$211

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 3/13

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 3/23

11:00 am-1:42 pm

Nonstop1h 42m

$217

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 11/11

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 11/18

11:00 am-1:42 pm

Nonstop1h 42m

$253

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 12/26

6:00 am-11:06 am

1 stop6h 06m

Chicago Midway

Mon 12/29

11:48 am-11:20 pm

1 stop10h 32m

$264

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 12/23

6:00 am-11:06 am

1 stop6h 06m

Chicago Midway

Sat 12/27

11:48 am-11:20 pm

1 stop10h 32m

$266

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 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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Canada, with most prices found around $172. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Canada during the month May is also very affordable. Most momondo users find prices during this month for around $206.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Canada. The lowest ticket price found for a Saturday 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, Thursday 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 $290.

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 $120 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $268. 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

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

There are 4 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?

No. A direct flight is the cheapest option for a flight between Canada to Chicago Midway Airport.

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

$176

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 $176. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is $286.
The fastest flight from Canada to Chicago Midway Airport takes 1h 50m
Direct flights go from Canada to Chicago Midway Airport every day.
Search flight deals

  • 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 $158Free CancellationRating
8.0
382 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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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