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Cheap flights from Chicago to Canada from C$ 92

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Canada departing on 5/1. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 244WestJet
Find Deal
Fri, 16 Jan - Mon, 19 Jan
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 245WestJet
Find Deal
Fri, 16 Jan - Mon, 19 Jan
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
C$ 271Porter Airlines
Find Deal
Fri, 5 Dec - Sun, 7 Dec
Multiple Airlines Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
Multiple Airlines Logo
5:35 a.m. - 3:10 p.m.YYC-ORD
8h 35m1 stop
C$ 271Multiple Airlines
Find Deal
Fri, 28 Nov - Thu, 4 Dec
Porter Airlines Logo
12:45 p.m. - 3:27 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
C$ 272Porter Airlines
Find Deal
Sat, 28 Feb - Fri, 13 Mar
Air Canada Logo
3:55 p.m. - 6:34 p.m.ORD-YYZ
1h 39mdirect
Air Canada Logo
6:30 p.m. - 7:30 p.m.YYZ-ORD
2h 00mdirect
C$ 277Air Canada
Find Deal
Thu, 11 Dec - Sun, 14 Dec
Multiple Airlines Logo
11:44 a.m. - 11:44 a.m.ORD-YYC
25h 00m1 stop
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 278Multiple Airlines
Find Deal
Mon, 15 Dec - Fri, 26 Dec
Air Canada Logo
10:00 a.m. - 6:54 p.m.ORD-YYC
9h 54m1 stop
Air Canada Logo
5:35 a.m. - 3:10 p.m.YYC-ORD
8h 35m1 stop
C$ 279Air Canada
Find Deal
Fri, 28 Nov - Thu, 4 Dec
United Airlines Logo
4:40 p.m. - 7:24 p.m.ORD-YYZ
1h 44mdirect
United Airlines Logo
9:00 a.m. - 10:09 a.m.YYZ-ORD
2h 09mdirect
C$ 291United Airlines
Find Deal
Sat, 7 Mar - Sun, 8 Mar
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
United Airlines Logo
12:37 p.m. - 5:10 p.m.YYC-ORD
3h 33mdirect
C$ 303United Airlines
Find Deal
Fri, 28 Nov - Thu, 4 Dec

American Airlines flights from Chicago to Canada

Our best American Airlines deals on Chicago to Canada flight tickets
American Airlines
28 Nov
ORD5:00 a.m.Chicago O'Hare Intl
5h 03m
1 stop
YYZ11:03 a.m.Toronto Pearson Intl
5 Dec
YYZ6:00 a.m.Toronto Pearson Intl
2h 15m
ORD7:15 a.m.Chicago O'Hare Intl
C$ 274
Find similar
American Airlines
5 Dec
ORD1:16 p.m.Chicago O'Hare Intl
1h 47m
YYZ4:03 p.m.Toronto Pearson Intl
7 Dec
YYZ6:00 a.m.Toronto Pearson Intl
6h 03m
1 stop
ORD11:03 a.m.Chicago O'Hare Intl
C$ 282
Find similar
American Airlines
14 Feb
ORD11:50 a.m.Chicago O'Hare Intl
2h 19m
YUL3:09 p.m.Montreal Pierre Elliott Trudeau Intl
21 Feb
YUL12:59 p.m.Montreal Pierre Elliott Trudeau Intl
22h 11m
1 stop
ORD10:10 a.m.Chicago O'Hare Intl
C$ 285
Find similar

United Airlines flights from Chicago to Canada

Our best United Airlines deals on Chicago to Canada flight tickets
United Airlines
7 Mar
ORD4:40 p.m.Chicago O'Hare Intl
1h 44m
YYZ7:24 p.m.Toronto Pearson Intl
8 Mar
YYZ9:00 a.m.Toronto Pearson Intl
2h 09m
ORD10:09 a.m.Chicago O'Hare Intl
C$ 291
Find similar
United Airlines
28 Nov
ORD8:45 a.m.Chicago O'Hare Intl
3h 50m
YYC11:35 a.m.Calgary
4 Dec
YYC12:37 p.m.Calgary
3h 33m
ORD5:10 p.m.Chicago O'Hare Intl
C$ 303
Find similar
United Airlines
10 Jan
ORD7:00 a.m.Chicago O'Hare Intl
8h 20m
1 stop
YYC2:20 p.m.Calgary
17 Jan
YYC12:37 p.m.Calgary
3h 31m
ORD5:08 p.m.Chicago O'Hare Intl
C$ 306
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Canada 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 6 November 2025.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 16/1

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

Calgary

Mon 19/1

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

C$ 244

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 16/1

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

Calgary

Mon 19/1

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

C$ 245

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 5/12

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

Nonstop1h 42m

Toronto Island

Sun 7/12

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

Nonstop1h 50m

C$ 271

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 28/11

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

Calgary

Thu 4/12

5:35 a.m.-3:10 p.m.

1 stop8h 35m

C$ 271

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 28/2

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

Nonstop1h 42m

Toronto Island

Fri 13/3

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

Nonstop1h 50m

C$ 272

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 11/12

3:55 p.m.-6:34 p.m.

Nonstop1h 39m

Toronto Pearson Intl

Sun 14/12

6:30 p.m.-7:30 p.m.

Nonstop2h 00m

C$ 276

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/12

11:44 a.m.-11:44 a.m.

1 stop25h 00m

Calgary

Fri 26/12

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

C$ 278

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 28/11

10:00 a.m.-6:54 p.m.

1 stop9h 54m

Calgary

Thu 4/12

5:35 a.m.-3:10 p.m.

1 stop8h 35m

C$ 279

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 7/3

4:40 p.m.-7:24 p.m.

Nonstop1h 44m

Toronto Pearson Intl

Sun 8/3

9:00 a.m.-10:09 a.m.

Nonstop2h 09m

C$ 291

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 28/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Thu 4/12

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 303

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 Canada from

How to get the cheapest flight ticket from Chicago to Canada

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 Canada?

In general, September is the cheapest month to fly from Chicago to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 295. If you’re not able to fly to Canada in September, then July is your next best option. Flight prices from Chicago to Canada during July average around C$ 330.

What is the cheapest day to depart on your flight to Canada?

Our data shows that Thursday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 329. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 520. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

What is the cheapest time of day to depart on your flight to Canada?

According to our data, the cheapest time of day to fly to Canada is in the evening. momondo users have found flights departing from Chicago to Canada in the evening for as low as C$ 316. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 478 per ticket.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Toronto Pearson Intl for the best Chicago - Canada flight prices

How far in advance should I book a flight to Canada?

You are more likely to see cheaper flights to Canada from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Canada for around C$ 434 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Canada from Chicago for as low as C$ 234 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Canada 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 Chicago to Canada flights?

You could potentially save up to 63% on your flight if you consider stops on a Chicago to Canada flight.

Cheap Chicago to Canada flight deals and tips

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

Best price found

C$ 130

Fastest flight time

1h 39m

Direct flights

Every day

Airports in Canada

2 airports
The best one-way flight to Canada from Chicago in the past 72 hours is C$ 130. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is C$ 126.
The fastest flight from Chicago to Canada takes 1h 39m
Direct flights go from Chicago to Canada every day.
There are 2 airports near Canada: Toronto Pearson Intl (YYZ), Toronto Island (YTZ)
Search flight deals

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

    Prices for flights from Chicago to Canada refresh daily.

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

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

    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 Chicago to Canada.

  • What documentation or ID do you need to fly to Canada?

    The necessary travel and health documents for your Canada trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Chicago to Canada

Compare and see reviews for airlines that fly from Chicago to Canada with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom C$ 154Free CancellationRating
7.2
11,041 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 174Free CancellationRating
7.4
9,003 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 208Free CancellationRating
7.1
10,410 reviews
Search Air Canada flights
WestJetPriceFrom C$ 216Free CancellationRating
7.2
3,154 reviews
Search WestJet flights

Why use momondo?

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

It is quick and easy to find Chicago to Canada flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Canada that suits you.

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

momondo does allow users to show only those flights to Canada from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

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 Canada from Chicago.

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

Yes. momondo can track prices for Chicago to Canada 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.

An easier way to manage your Canada trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to Canada

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