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Cheap flights from Canada to Chicago Midway Airport from C$ 188

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 6/12. 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 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 290Porter Airlines
Find Deal
Wed, 25 Dec - Sat, 25 Jan
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 293Porter Airlines
Find Deal
Thu, 28 Nov - Mon, 2 Dec
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
9:34 a.m. - 8:53 p.m.MDW-YYC
12h 19m2 stops
C$ 308Delta
Find Deal
Thu, 9 Jan - Sun, 12 Jan
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 347Air Transat
Find Deal
Thu, 28 Nov - Mon, 2 Dec
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
9:34 a.m. - 8:53 p.m.MDW-YYC
12h 19m2 stops
C$ 351Delta
Find Deal
Mon, 27 Jan - Thu, 30 Jan
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 351Air Transat
Find Deal
Thu, 28 Nov - Mon, 2 Dec
12:45 a.m. - 11:29 p.m.YEG-MDW
21h 44m1 stop
6:22 p.m. - 12:00 p.m.MDW-YEG
18h 38m1 stop
C$ 360
Find Deal
Fri, 6 Dec - Mon, 16 Dec
11:00 p.m. - 11:29 p.m.YVR-MDW
22h 29m1 stop
6:17 p.m. - 11:15 a.m.MDW-YVR
18h 58m1 stop
C$ 361
Find Deal
Fri, 6 Dec - Mon, 9 Dec
6:30 a.m. - 1:35 p.m.YYZ-MDW
8h 05m1 stop
2:15 p.m. - 11:34 p.m.MDW-YYZ
8h 19m1 stop
C$ 423WestJet
Find Deal
Tue, 3 Dec - Tue, 10 Dec
6:30 a.m. - 6:32 p.m.YYZ-MDW
13h 02m1 stop
12:44 p.m. - 7:06 p.m.MDW-YYZ
5h 22m1 stop
C$ 424WestJet
Find Deal
Sat, 7 Dec - Tue, 10 Dec
11:00 p.m. - 11:29 p.m.YVR-MDW
22h 29m1 stop
C$ 188
Find Deal
Fri, 6 Dec
8:00 a.m. - 10:06 p.m.YYC-MDW
13h 06m2 stops
C$ 190Delta
Find Deal
Sat, 7 Dec
8:35 p.m. - 3:11 p.m.YVR-MDW
16h 36m2 stops
C$ 190
Find Deal
Mon, 16 Dec
7:30 a.m. - 10:38 a.m.YWG-MDW
27h 08m1 stop
C$ 191
Find Deal
Mon, 18 Nov
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
C$ 195Porter Airlines
Find Deal
Thu, 5 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 197Porter Airlines
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Wed, 1 Jan
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
C$ 212Air Transat
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Tue, 11 Feb
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 215Air Transat
Find Deal
Tue, 10 Dec
6:30 a.m. - 6:32 p.m.YYZ-MDW
13h 02m1 stop
C$ 244WestJet
Find Deal
Sat, 7 Dec
6:30 a.m. - 6:32 p.m.YYZ-MDW
13h 02m1 stop
C$ 261WestJet
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Mon, 9 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 492Porter Airlines
Find Deal
Wed, 6 Nov - Sun, 17 Nov
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 538Porter Airlines
Find Deal
Sat, 9 Nov - Tue, 12 Nov
11:39 a.m. - 9:38 p.m.YYZ-MDW
10h 59m1 stop
9:30 a.m. - 11:34 p.m.MDW-YYZ
13h 04m1 stop
C$ 565WestJet
Find Deal
Sat, 9 Nov - Tue, 12 Nov
1:25 p.m. - 9:38 p.m.YYZ-MDW
9h 13m1 stop
12:43 p.m. - 11:59 p.m.MDW-YYZ
10h 16m1 stop
C$ 615WestJet
Find Deal
Sat, 9 Nov - Mon, 11 Nov
6:50 a.m. - 12:00 p.m.YUL-MDW
6h 10m1 stop
2:17 p.m. - 11:33 p.m.MDW-YUL
8h 16m1 stop
C$ 640
Find Deal
Sat, 9 Nov - Wed, 20 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 651Air Transat
Find Deal
Fri, 8 Nov - Sun, 10 Nov
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
10:32 p.m. - 4:35 p.m.MDW-YUL
17h 03m1 stop
C$ 668
Find Deal
Thu, 7 Nov - Mon, 11 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 689Air Transat
Find Deal
Wed, 6 Nov - Sat, 9 Nov
6:00 a.m. - 8:55 a.m.YYZ-MDW
3h 55m1 stop
1:30 p.m. - 10:36 p.m.MDW-YYZ
8h 06m1 stop
C$ 860Delta
Find Deal
Sat, 9 Nov - Mon, 11 Nov
9:45 a.m. - 5:03 p.m.YYZ-MDW
8h 18m1 stop
9:35 a.m. - 6:28 p.m.MDW-YYZ
7h 53m1 stop
C$ 985Delta
Find Deal
Fri, 8 Nov - Sun, 10 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 290Porter Airlines
Find Deal
Wed, 25 Dec - Sat, 25 Jan
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 293Porter Airlines
Find Deal
Thu, 28 Nov - Mon, 2 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 294Porter Airlines
Find Deal
Sun, 22 Dec - Wed, 25 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 297Porter Airlines
Find Deal
Wed, 4 Dec - Sun, 8 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 300Porter Airlines
Find Deal
Mon, 25 Nov - Fri, 29 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 303Porter Airlines
Find Deal
Thu, 28 Nov - Mon, 2 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 347Air Transat
Find Deal
Thu, 28 Nov - Mon, 2 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 351Air Transat
Find Deal
Thu, 28 Nov - Mon, 2 Dec
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 363Air Transat
Find Deal
Thu, 30 Jan - Tue, 4 Feb
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 943
Find Deal
Fri, 15 Nov - Sun, 17 Nov

Air Transat flights from Canada to Chicago Midway Airport

Our best Air Transat deals on Canada to Chicago Midway Airport flight tickets
Air Transat
28 Nov
YTZ9:30 a.m.Toronto Island
1h 50m
MDW10:20 a.m.Chicago Midway
2 Dec
MDW5:35 p.m.Chicago Midway
1h 42m
YTZ8:17 p.m.Toronto Island
Air Transat
28 Nov
YTZ9:30 a.m.Toronto Island
1h 50m
MDW10:20 a.m.Chicago Midway
2 Dec
MDW12:05 p.m.Chicago Midway
1h 42m
YTZ2:47 p.m.Toronto Island
Air Transat
30 Jan
YTZ11:10 a.m.Toronto Island
1h 50m
MDW12:00 p.m.Chicago Midway
4 Feb
MDW12:55 p.m.Chicago Midway
1h 42m
YTZ3:37 p.m.Toronto Island

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets
Porter Airlines
25 Dec
YTZ3:50 p.m.Toronto Island
1h 50m
MDW4:40 p.m.Chicago Midway
25 Jan
MDW12:55 p.m.Chicago Midway
1h 42m
YTZ3:37 p.m.Toronto Island
Porter Airlines
28 Nov
YTZ9:30 a.m.Toronto Island
1h 50m
MDW10:20 a.m.Chicago Midway
2 Dec
MDW5:35 p.m.Chicago Midway
1h 42m
YTZ8:17 p.m.Toronto Island
Porter Airlines
22 Dec
YTZ9:30 a.m.Toronto Island
1h 50m
MDW10:20 a.m.Chicago Midway
25 Dec
MDW5:35 p.m.Chicago Midway
1h 42m
YTZ8:17 p.m.Toronto Island

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 airline that flies to Chicago Midway Airport from Canada?

Porter Airlines. Porter Airlines and WestJet are the most popular carriers operating from Canada to Chicago Midway Airport

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$ 188

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$ 188. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is C$ 290.
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 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$ 270Free CancellationRating
7.8
293 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 442Free CancellationRating
7.3
2,803 reviews
Search WestJet 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?

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.


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