Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Canada from C$ 93

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 15/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Canada

Cheap round-trip flights

WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 192WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 193WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
United Airlines Logo
12:35 p.m. - 5:10 p.m.YYC-ORD
3h 35mdirect
C$ 222United Airlines
Find Deal
Wed, 10 Dec - Sat, 13 Dec
Air Canada Logo
7:15 a.m. - 2:19 p.m.ORD-YQB
6h 04m1 stop
Air Canada Logo
6:00 a.m. - 11:18 a.m.YQB-ORD
6h 18m1 stop
C$ 224Air Canada
Find Deal
Thu, 30 Oct - Mon, 3 Nov
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
United Airlines Logo
12:35 p.m. - 5:10 p.m.YYC-ORD
3h 35mdirect
C$ 224United Airlines
Find Deal
Wed, 10 Dec - Sat, 13 Dec
Air Canada Logo
3:40 p.m. - 6:15 p.m.ORD-YVR
4h 35mdirect
Air Canada Logo
8:30 a.m. - 2:41 p.m.YVR-ORD
4h 11mdirect
C$ 236Air Canada
Find Deal
Wed, 29 Oct - Wed, 5 Nov
Multiple Airlines Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
Multiple Airlines Logo
11:15 a.m. - 3:49 p.m.YYC-ORD
27h 34m1 stop
C$ 251Multiple Airlines
Find Deal
Sun, 26 Oct - Sun, 2 Nov
Multiple Airlines Logo
1:26 p.m. - 8:26 p.m.ORD-YYC
8h 00m1 stop
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 258Multiple Airlines
Find Deal
Thu, 30 Oct - Sun, 2 Nov
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
C$ 332Porter Airlines
Find Deal
Sat, 18 Oct - Sun, 19 Oct
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
C$ 333Porter Airlines
Find Deal
Sun, 12 Oct - Sun, 19 Oct

WestJet flights from Chicago to Canada

Our best WestJet deals on Chicago to Canada flight tickets
WestJet
23 Oct
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
27 Oct
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
C$ 192
Find similar
WestJet
23 Oct
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
27 Oct
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
C$ 193
Find similar
WestJet
23 Oct
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
26 Oct
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
C$ 200
Find similar

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets
Air Canada
30 Oct
ORD7:15 a.m.Chicago O'Hare Intl
6h 04m
1 stop
YQB2:19 p.m.Québec City
3 Nov
YQB6:00 a.m.Québec City
6h 18m
1 stop
ORD11:18 a.m.Chicago O'Hare Intl
C$ 224
Find similar
Air Canada
29 Oct
ORD3:40 p.m.Chicago O'Hare Intl
4h 35m
YVR6:15 p.m.Vancouver Intl
5 Nov
YVR8:30 a.m.Vancouver Intl
4h 11m
ORD2:41 p.m.Chicago O'Hare Intl
C$ 236
Find similar
Air Canada
29 Oct
ORD10:00 a.m.Chicago O'Hare Intl
8h 04m
1 stop
YYC5:04 p.m.Calgary
5 Nov
YYC5:45 a.m.Calgary
8h 25m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
C$ 239
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 16 September 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

Thu 23/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Mon 27/10

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

Nonstop3h 35m

C$ 192

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 23/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Mon 27/10

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

Nonstop3h 35m

C$ 193

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 10/12

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

Nonstop3h 50m

Calgary

Sat 13/12

12:35 p.m.-5:10 p.m.

Nonstop3h 35m

C$ 222

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Thu 30/10

7:15 a.m.-2:19 p.m.

1 stop6h 04m

Québec City

Mon 3/11

6:00 a.m.-11:18 a.m.

1 stop6h 18m

C$ 224

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 10/12

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

Nonstop3h 50m

Calgary

Sat 13/12

12:35 p.m.-5:10 p.m.

Nonstop3h 35m

C$ 224

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Wed 29/10

3:40 p.m.-6:15 p.m.

Nonstop4h 35m

Vancouver Intl

Wed 5/11

8:30 a.m.-2:41 p.m.

Nonstop4h 11m

C$ 236

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 26/10

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

Nonstop3h 55m

Calgary

Sun 2/11

11:15 a.m.-3:49 p.m.

1 stop27h 34m

C$ 251

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 30/10

1:26 p.m.-8:26 p.m.

1 stop8h 00m

Calgary

Sun 2/11

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

Nonstop3h 35m

C$ 258

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 18/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 19/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 332

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 12/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 19/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 333

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, July 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$ 323. If you’re not able to fly to Canada in July, then September is your next best option. Flight prices from Chicago to Canada during September average around C$ 356.

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

Our data shows that Saturday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 334. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 580. 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$ 317. 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$ 464 per ticket.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Vancouver 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$ 420 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$ 229 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 30% 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$ 110

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$ 110. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is C$ 170.
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
United AirlinesPriceFrom C$ 141Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 203Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
WestJetPriceFrom C$ 211Free CancellationRating
7.2
3,093 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 16/10
Thu 23/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada

Popular Cities in Canada

Popular flights according to clicks in the last 7 days on momondo
Flights to Torontofrom C$ 101
Flights to Vancouverfrom C$ 55
Flights to Montrealfrom C$ 188
Flights to Calgaryfrom C$ 69
Flights to Ottawafrom C$ 160
Flights to Winnipegfrom C$ 109
Flights to Halifaxfrom C$ 120
Flights to Kelownafrom C$ 69
Flights to Saskatoonfrom C$ 122
Flights to Reginafrom C$ 102
Flights to St. John'sfrom C$ 149
Flights to Québec Cityfrom C$ 293