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Cheap flights from Canada to Chicago Midway Airport from C$ 186

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 14/12. 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
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 306Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
1:26 p.m. - 8:53 p.m.MDW-YYC
8h 27m1 stop
C$ 309Delta
Find Deal
Sat, 25 Jan - Mon, 27 Jan
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Fri, 13 Dec - Tue, 17 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 318Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
7:30 a.m. - 4:14 p.m.YWG-MDW
8h 44m1 stop
6:40 a.m. - 3:10 p.m.MDW-YWG
8h 30m1 stop
C$ 345
Find Deal
Tue, 14 Jan - Fri, 24 Jan
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 356Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
7:30 a.m. - 4:14 p.m.YWG-MDW
8h 44m1 stop
6:15 a.m. - 3:10 p.m.MDW-YWG
8h 55m1 stop
C$ 364
Find Deal
Tue, 7 Jan - Mon, 13 Jan
6:30 a.m. - 6:32 p.m.YYZ-MDW
13h 02m1 stop
9:38 a.m. - 11:34 p.m.MDW-YYZ
12h 56m1 stop
C$ 373WestJet
Find Deal
Thu, 12 Dec - Mon, 16 Dec
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
11:19 a.m. - 11:11 p.m.MDW-YYZ
10h 52m1 stop
C$ 378WestJet
Find Deal
Tue, 7 Jan - Sat, 11 Jan
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
C$ 186Porter Airlines
Find Deal
Sat, 14 Dec
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
C$ 190Porter Airlines
Find Deal
Sat, 14 Dec
7:30 a.m. - 5:50 p.m.YWG-MDW
10h 20m1 stop
C$ 197
Find Deal
Fri, 10 Jan
9:15 p.m. - 5:57 p.m.YVR-MDW
18h 42m2 stops
C$ 198
Find Deal
Tue, 7 Jan
12:30 p.m. - 5:01 p.m.YYZ-MDW
5h 31m1 stop
C$ 230Delta
Find Deal
Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 237Air Transat
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Mon, 6 Jan
12:45 p.m. - 6:00 p.m.YUL-MDW
6h 15m1 stop
C$ 239WestJet
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Sat, 19 Apr
12:25 p.m. - 10:06 p.m.YYZ-MDW
10h 41m1 stop
C$ 243WestJet
Find Deal
Sat, 14 Dec
10:10 a.m. - 1:08 p.m.YYZ-MDW
3h 58m1 stop
C$ 246Delta
Find Deal
Mon, 6 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 283Air Transat
Find Deal
Sat, 21 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$ 524Porter Airlines
Find Deal
Mon, 25 Nov - Mon, 9 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 529Air Transat
Find Deal
Tue, 26 Nov - Sat, 18 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$ 559Porter Airlines
Find Deal
Tue, 26 Nov - Fri, 6 Dec
2:55 p.m. - 6:32 p.m.YYZ-MDW
4h 37m1 stop
9:30 a.m. - 11:41 p.m.MDW-YYZ
13h 11m1 stop
C$ 566WestJet
Find Deal
Tue, 26 Nov - Tue, 3 Dec
6:00 a.m. - 6:32 p.m.YUL-MDW
13h 32m1 stop
2:17 p.m. - 11:33 p.m.MDW-YUL
8h 16m1 stop
C$ 567WestJet
Find Deal
Sun, 24 Nov - Wed, 27 Nov
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$ 575Air Transat
Find Deal
Tue, 26 Nov - Wed, 4 Dec
8:00 p.m. - 7:55 a.m.YYZ-MDW
12h 55m1 stop
12:43 p.m. - 7:06 p.m.MDW-YYZ
5h 23m1 stop
C$ 649
Find Deal
Sun, 24 Nov - Tue, 3 Dec
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$ 695
Find Deal
Mon, 25 Nov - Sat, 30 Nov
6:00 a.m. - 12:49 p.m.YYZ-MDW
7h 49m1 stop
2:17 p.m. - 11:34 p.m.MDW-YYZ
8h 17m1 stop
C$ 716Delta
Find Deal
Mon, 25 Nov - Sun, 1 Dec
7:10 a.m. - 12:49 p.m.YUL-MDW
6h 39m1 stop
1:30 p.m. - 11:11 p.m.MDW-YUL
8h 41m1 stop
C$ 728Delta
Find Deal
Sat, 23 Nov - Tue, 26 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$ 306Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Fri, 13 Dec - Tue, 17 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 318Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 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$ 321Porter Airlines
Find Deal
Fri, 13 Dec - Sun, 15 Dec
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$ 331Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 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$ 334Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 356Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 366Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 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$ 466
Find Deal
Wed, 18 Dec - Sun, 5 Jan

Porter Airlines flights from Canada to Chicago Midway Airport

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

WestJet flights from Canada to Chicago Midway Airport

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

In general, December 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$ 295. 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 C$ 306.

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 Wednesday when prices can be found for as low as C$ 338. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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$ 402.

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$ 365. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 405.

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?

The best time to book a flight to Chicago Midway Airport from Canada is 24 days out, which is when prices tend to be around C$ 363. Keep in mind that you might be able to find cheaper flights to Chicago Midway Airport at any time. In fact, our users found flights for as low as C$ 332 in the past 72 hours.

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

There are 1 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 3% 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

C$ 186

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$ 186. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is C$ 306.
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$ 271Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 443Free CancellationRating
7.3
2,811 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.


An easier way to manage your Chicago Midway Airport trip

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