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Cheap flights from Canada to Chicago from C$ 113

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 23/5. 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

Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.
WestJet Logo
12:15 p.m. - 4:43 p.m.
YYC
-
ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.
ORD
-
YYC
3h 49mdirect
C$ 203WestJet
Thu, 21 May - Sat, 30 May
WestJet Logo
12:15 p.m. - 4:43 p.m.
YYC
-
ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.
ORD
-
YYC
3h 49mdirect
C$ 204WestJet
Sun, 24 May - Sat, 30 May
United Airlines Logo
2:13 p.m. - 11:59 p.m.
YYC
-
ORD
8h 46m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.
ORD
-
YYC
3h 50mdirect
C$ 222United Airlines
Tue, 3 Feb - Wed, 4 Feb
Air Canada Logo
8:00 a.m. - 5:48 p.m.
YYC
-
ORD
8h 48m1 stop
Air Canada Logo
3:55 p.m. - 12:14 a.m.
ORD
-
YYC
9h 19m1 stop
C$ 242Air Canada
Tue, 3 Feb - Wed, 4 Feb
United Airlines Logo
6:15 a.m. - 11:59 p.m.
YYC
-
ORD
16h 44m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.
ORD
-
YYC
3h 50mdirect
C$ 251United Airlines
Mon, 2 Feb - Tue, 3 Feb
American Airlines Logo
1:14 p.m. - 2:14 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
9:41 a.m. - 12:34 p.m.
ORD
-
YYZ
1h 53mdirect
C$ 251American Airlines
Fri, 23 Jan - Sun, 1 Feb
Air Canada Logo
4:50 p.m. - 5:48 p.m.
YYZ
-
ORD
1h 58mdirect
Air Canada Logo
8:00 a.m. - 10:40 a.m.
ORD
-
YYZ
1h 40mdirect
C$ 252Air Canada
Sat, 31 Jan - Sat, 7 Feb
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.
YYC
-
ORD
3h 35mdirect
Multiple Airlines Logo
4:19 p.m. - 9:45 p.m.
ORD
-
YYC
30h 26m1 stop
C$ 252Multiple Airlines
Fri, 23 Jan - Sun, 1 Feb
Multiple Airlines Logo
7:00 a.m. - 5:44 p.m.
YYC
-
ORD
9h 44m1 stop
Multiple Airlines Logo
2:20 p.m. - 5:15 p.m.
ORD
-
YYC
3h 55mdirect
C$ 255Multiple Airlines
Fri, 16 Jan - Fri, 23 Jan
American Airlines Logo
7:04 p.m. - 8:04 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
6:31 p.m. - 9:23 p.m.
ORD
-
YYZ
1h 52mdirect
C$ 259American Airlines
Sat, 24 Jan - Sun, 1 Feb

American Airlines flights from Canada to Chicago O'Hare Intl Airport

Our best American Airlines deals on Canada to Chicago O'Hare Intl Airport flight tickets
American Airlines
23 Jan
YYZ1:14 p.m.Toronto Pearson Intl
2h 00m
ORD2:14 p.m.Chicago O'Hare Intl
1 Feb
ORD9:41 a.m.Chicago O'Hare Intl
1h 53m
YYZ12:34 p.m.Toronto Pearson Intl
C$ 251
Find similar
American Airlines
1 Feb
YYZ12:39 p.m.Toronto Pearson Intl
8h 36m
1 stop
ORD8:15 p.m.Chicago O'Hare Intl
8 Feb
ORD8:12 a.m.Chicago O'Hare Intl
8h 28m
1 stop
YYZ5:40 p.m.Toronto Pearson Intl
C$ 260
Find similar
American Airlines
5 Feb
YYZ11:35 a.m.Toronto Pearson Intl
1h 55m
ORD12:30 p.m.Chicago O'Hare Intl
8 Feb
ORD8:07 a.m.Chicago O'Hare Intl
1h 46m
YYZ10:53 a.m.Toronto Pearson Intl
C$ 263
Find similar

WestJet flights from Canada to Chicago O'Hare Intl Airport

Our best WestJet deals on Canada to Chicago O'Hare Intl Airport flight tickets
WestJet
21 May
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
30 May
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
C$ 203
Find similar
WestJet
24 May
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
30 May
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
C$ 204
Find similar
WestJet
17 Apr
YEG6:00 a.m.Edmonton
6h 35m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
27 Apr
ORD5:30 p.m.Chicago O'Hare Intl
7h 55m
1 stop
YEG12:25 a.m.Edmonton
C$ 260
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Canada to Chicago O'Hare Intl 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 18 December 2025.
Use the filters below to find and compare flights from Canada to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 21/5

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sat 30/5

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

Nonstop3h 49m

C$ 203

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 24/5

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sat 30/5

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

Nonstop3h 49m

C$ 204

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/2

2:13 p.m.-11:59 p.m.

1 stop8h 46m

Chicago O'Hare Intl

Wed 4/2

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

Nonstop3h 50m

C$ 222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/2

8:00 a.m.-5:48 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Wed 4/2

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 242

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:15 a.m.-11:59 p.m.

1 stop16h 44m

Chicago O'Hare Intl

Tue 3/2

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

Nonstop3h 50m

C$ 251

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 23/1

1:14 p.m.-2:14 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 1/2

9:41 a.m.-12:34 p.m.

Nonstop1h 53m

C$ 251

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 31/1

4:50 p.m.-5:48 p.m.

Nonstop1h 58m

Chicago O'Hare Intl

Sat 7/2

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 252

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 23/1

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

Nonstop3h 35m

Chicago O'Hare Intl

Sun 1/2

4:19 p.m.-9:45 p.m.

1 stop30h 26m

C$ 252

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 16/1

7:00 a.m.-5:44 p.m.

1 stop9h 44m

Chicago O'Hare Intl

Fri 23/1

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

Nonstop3h 55m

C$ 255

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 24/1

7:04 p.m.-8:04 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 1/2

6:31 p.m.-9:23 p.m.

Nonstop1h 52m

C$ 259

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 Chicago from

How to get the cheapest flight ticket from Canada to Chicago O'Hare Intl 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 O'Hare Intl Airport?

In general, November is the cheapest month to fly from Canada to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 298. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Canada averaging around C$ 362.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 670. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Canada to Chicago O'Hare Intl Airport for around C$ 1,088.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Canada to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 627. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 1,113 on average. Flights to Chicago O'Hare Intl Airport from Canada at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Canada to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 401 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Canada for as low as C$ 269 on momondo.

What cabin class options are available on Canada to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Canada to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Canada to Chicago O'Hare Intl Airport.

Cheap Canada to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago O'Hare Intl Airport

Best price found

C$ 162

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Canada in the past 72 hours is C$ 162. The best round-trip flight deal from Canada to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 363.
The fastest flight from Canada to Chicago O'Hare Intl Airport takes 1h 55m
Direct flights go from Canada to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Canada to Chicago O'Hare Intl Airport?

    Prices for flights from Canada to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Canada to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Canada to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Canada to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Canada to Chicago O'Hare Intl Airport?

Best airlines flying from Canada to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Canada to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 149Free CancellationRating
7.1
10,534 reviews
Search Air Canada flights
WestJetPriceFrom C$ 176Free CancellationRating
7.2
3,204 reviews
Search WestJet flights
DeltaPriceFrom C$ 184Free CancellationRating
7.9
8,006 reviews
Search Delta flights
American AirlinesPriceFrom C$ 185Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 194Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights
Porter AirlinesPriceFrom C$ 222Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Northbrook
Tinley Park
Munster
Skokie
Hammond
Harvey
Naperville
Glenview
Great Lakes
Wheeling
Elmhurst
Harvard
Merrillville
Elk Grove Village
Oak Brook
Kenosha

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?

momondo provides multiple filters to help you find the best flight to Chicago from Canada. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Canada are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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