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Cheap flights from Canada to Chicago from C$ 157

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 26/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 262Multiple Airlines
Find Deal
Fri, 16 Jan - Sun, 25 Jan
Porter Airlines Logo
11:00 a.m. - 11:50 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
12:45 p.m. - 3:27 p.m.MDW-YTZ
1h 42mdirect
C$ 265Porter Airlines
Find Deal
Sat, 28 Feb - Sat, 7 Mar
Multiple Airlines Logo
7:30 a.m. - 10:12 p.m.YWG-MDW
14h 42m1 stop
Multiple Airlines Logo
6:15 a.m. - 3:07 p.m.MDW-YWG
8h 52m1 stop
C$ 266Multiple Airlines
Find Deal
Fri, 5 Dec - Sun, 7 Dec
Porter Airlines Logo
11:00 a.m. - 11:50 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 267Porter Airlines
Find Deal
Sat, 28 Feb - Sun, 8 Mar
Delta Logo
12:13 p.m. - 6:00 p.m.YYZ-MDW
6h 47m1 stop
Delta Logo
6:40 p.m. - 11:11 p.m.MDW-YYZ
3h 31m1 stop
C$ 281Delta
Find Deal
Thu, 4 Dec - Mon, 8 Dec
Delta Logo
12:13 p.m. - 6:00 p.m.YYZ-MDW
6h 47m1 stop
Delta Logo
6:40 p.m. - 11:11 p.m.MDW-YYZ
3h 31m1 stop
C$ 294Delta
Find Deal
Thu, 4 Dec - Mon, 8 Dec
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 304Air Transat
Find Deal
Fri, 13 Mar - Mon, 23 Mar
Air Transat Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 354Air Transat
Find Deal
Tue, 11 Nov - Tue, 18 Nov
WestJet Logo
6:00 a.m. - 11:06 a.m.YYZ-MDW
6h 06m1 stop
WestJet Logo
11:48 a.m. - 11:20 p.m.MDW-YYZ
10h 32m1 stop
C$ 370WestJet
Find Deal
Fri, 26 Dec - Mon, 29 Dec
WestJet Logo
6:00 a.m. - 11:06 a.m.YYZ-MDW
6h 06m1 stop
WestJet Logo
11:48 a.m. - 11:20 p.m.MDW-YYZ
10h 32m1 stop
C$ 372WestJet
Find Deal
Tue, 23 Dec - Sat, 27 Dec

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets
Porter Airlines
28 Feb
YTZ11:00 a.m.Toronto Island
1h 50m
MDW11:50 a.m.Chicago Midway
7 Mar
MDW12:45 p.m.Chicago Midway
1h 42m
YTZ3:27 p.m.Toronto Island
C$ 265
Find similar
Porter Airlines
28 Feb
YTZ11:00 a.m.Toronto Island
1h 50m
MDW11:50 a.m.Chicago Midway
8 Mar
MDW4:15 p.m.Chicago Midway
1h 42m
YTZ6:57 p.m.Toronto Island
C$ 267
Find similar
Porter Airlines
25 Feb
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
7 Mar
MDW12:45 p.m.Chicago Midway
1h 42m
YTZ3:27 p.m.Toronto Island
C$ 269
Find similar

Delta flights from Canada to Chicago Midway Airport

Our best Delta deals on Canada to Chicago Midway Airport flight tickets
Delta
4 Dec
YYZ12:13 p.m.Toronto Pearson Intl
6h 47m
1 stop
MDW6:00 p.m.Chicago Midway
8 Dec
MDW6:40 p.m.Chicago Midway
3h 31m
1 stop
YYZ11:11 p.m.Toronto Pearson Intl
C$ 281
Find similar
Delta
4 Dec
YYZ12:13 p.m.Toronto Pearson Intl
6h 47m
1 stop
MDW6:00 p.m.Chicago Midway
8 Dec
MDW6:40 p.m.Chicago Midway
3h 31m
1 stop
YYZ11:11 p.m.Toronto Pearson Intl
C$ 294
Find similar
Delta
21 Nov
YYZ6:05 a.m.Toronto Pearson Intl
7h 29m
1 stop
MDW12:34 p.m.Chicago Midway
27 Nov
MDW9:34 a.m.Chicago Midway
6h 41m
1 stop
YYZ5:15 p.m.Toronto Pearson Intl
C$ 295
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 96,600 searches. Data last updated 23 October 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 16/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 25/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 262

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 28/2

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Sat 7/3

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 265

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/12

7:30 a.m.-10:12 p.m.

1 stop14h 42m

Chicago Midway

Sun 7/12

6:15 a.m.-3:07 p.m.

1 stop8h 52m

C$ 266

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 28/2

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Sun 8/3

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 267

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/12

12:13 p.m.-6:00 p.m.

1 stop6h 47m

Chicago Midway

Mon 8/12

6:40 p.m.-11:11 p.m.

1 stop3h 31m

C$ 281

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/12

12:13 p.m.-6:00 p.m.

1 stop6h 47m

Chicago Midway

Mon 8/12

6:40 p.m.-11:11 p.m.

1 stop3h 31m

C$ 294

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 13/3

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 23/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 304

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 11/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Tue 18/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 354

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 26/12

6:00 a.m.-11:06 a.m.

1 stop6h 06m

Chicago Midway

Mon 29/12

11:48 a.m.-11:20 p.m.

1 stop10h 32m

C$ 370

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 23/12

6:00 a.m.-11:06 a.m.

1 stop6h 06m

Chicago Midway

Sat 27/12

11:48 a.m.-11:20 p.m.

1 stop10h 32m

C$ 372

Flights are sorted by cheapest round-trip flights 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?

In general, September is the cheapest month to fly from Canada to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 241. 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 C$ 288.

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

The cheapest day to depart on your flight to Chicago Midway Airport is on a Friday when prices can be found for as low as C$ 306. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 334.

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

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Canada to Chicago Midway Airport during this time can be as low as C$ 314. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 678.

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 is only 1 cabin class 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

C$ 197

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 C$ 197. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is C$ 347.
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 are updated daily.

  • 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?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify 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 C$ 198Free CancellationRating
8.0
383 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 556Free CancellationRating
7.2
3,139 reviews
Search WestJet flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

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?

All flight searches from Canada to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Canada to Chicago 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 Canada to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Canada. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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