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Cheap flights from Canada to Chicago from C$ 135

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 4/5. 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
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 221WestJet
Mon, 4 May - Thu, 7 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 223WestJet
Mon, 4 May - Mon, 11 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 226WestJet
Wed, 20 May - Fri, 29 May
Air Canada Logo
1:10 p.m. - 2:55 p.m.
YUL
-
ORD
2h 45mdirect
Air Canada Logo
12:50 p.m. - 4:05 p.m.
ORD
-
YUL
2h 15mdirect
C$ 239Air Canada
Thu, 26 Mar - Mon, 30 Mar
Air Canada Logo
6:25 p.m. - 8:10 p.m.
YUL
-
ORD
2h 45mdirect
Air Canada Logo
12:50 p.m. - 4:05 p.m.
ORD
-
YUL
2h 15mdirect
C$ 241Air Canada
Wed, 25 Mar - Mon, 30 Mar
United Airlines Logo
9:45 a.m. - 11:28 a.m.
YUL
-
ORD
2h 43mdirect
United Airlines Logo
4:25 p.m. - 12:13 a.m.
ORD
-
YUL
6h 48m
1 stop
C$ 253United Airlines
Fri, 1 May - Mon, 4 May
United Airlines Logo
6:00 a.m. - 8:00 a.m.
YUL
-
ORD
3h 00mdirect
United Airlines Logo
4:20 p.m. - 12:13 a.m.
ORD
-
YUL
6h 53m
1 stop
C$ 254United Airlines
Thu, 26 Mar - Mon, 30 Mar
American Airlines Logo
3:45 p.m. - 5:45 p.m.
YUL
-
ORD
3h 00mdirect
American Airlines Logo
6:44 p.m. - 1:45 p.m.
ORD
-
YUL
18h 01m
1 stop
C$ 262American Airlines
Thu, 12 Mar - Mon, 16 Mar
Lufthansa Logo
8:45 a.m. - 9:50 a.m.
YYZ
-
ORD
2h 05mdirect
Lufthansa Logo
6:28 p.m. - 9:21 p.m.
ORD
-
YYZ
1h 53mdirect
C$ 283Lufthansa
Fri, 27 Feb - Sun, 1 Mar
American Airlines Logo
2:24 p.m. - 4:29 p.m.
YQB
-
ORD
3h 05mdirect
American Airlines Logo
5:00 a.m. - 3:20 p.m.
ORD
-
YQB
9h 20m
1 stop
C$ 592American Airlines
Thu, 4 Jun - Mon, 8 Jun

Air Canada flights from Canada to Chicago O'Hare Intl Airport

Our best Air Canada deals on Canada to Chicago O'Hare Intl Airport flight tickets
Air Canada
26 Mar
YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD2:55 p.m.Chicago O'Hare Intl
30 Mar
ORD12:50 p.m.Chicago O'Hare Intl
2h 15m
YUL4:05 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 239
Air Canada
25 Mar
YUL6:25 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 p.m.Chicago O'Hare Intl
30 Mar
ORD12:50 p.m.Chicago O'Hare Intl
2h 15m
YUL4:05 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 241
Air Canada
8 Mar
YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD2:55 p.m.Chicago O'Hare Intl
15 Mar
ORD7:15 a.m.Chicago O'Hare Intl
2h 05m
YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl
C$ 249

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
12 Mar
YUL3:45 p.m.Montreal Pierre Elliott Trudeau Intl
3h 00m
ORD5:45 p.m.Chicago O'Hare Intl
16 Mar
ORD6:44 p.m.Chicago O'Hare Intl
18h 01m
1 stop
YUL1:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 262
American Airlines
18 Mar
YYZ11:40 a.m.Toronto Pearson Intl
1h 55m
ORD12:35 p.m.Chicago O'Hare Intl
25 Mar
ORD6:00 a.m.Chicago O'Hare Intl
8h 00m
1 stop
YYZ3:00 p.m.Toronto Pearson Intl
C$ 286
American Airlines
26 Feb
YYZ4:44 p.m.Toronto Pearson Intl
2h 00m
ORD5:44 p.m.Chicago O'Hare Intl
1 Mar
ORD5:00 a.m.Chicago O'Hare Intl
5h 13m
1 stop
YYZ11:13 a.m.Toronto Pearson Intl
C$ 288

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 8 February 2026.
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

Mon 4/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Thu 7/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 221

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 4/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Mon 11/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 223

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 20/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Fri 29/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 226

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 26/3

1:10 p.m.-2:55 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Mon 30/3

12:50 p.m.-4:05 p.m.

Nonstop2h 15m

C$ 239

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 25/3

6:25 p.m.-8:10 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Mon 30/3

12:50 p.m.-4:05 p.m.

Nonstop2h 15m

C$ 241

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 1/5

9:45 a.m.-11:28 a.m.

Nonstop2h 43m

Chicago O'Hare Intl

Mon 4/5

4:25 p.m.-12:13 a.m.

1 stop6h 48m

C$ 253

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 26/3

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

Mon 30/3

4:20 p.m.-12:13 a.m.

1 stop6h 53m

C$ 254

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 12/3

3:45 p.m.-5:45 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Mon 16/3

6:44 p.m.-1:45 p.m.

1 stop18h 01m

C$ 262

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/2

8:45 a.m.-9:50 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 1/3

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 283

Québec CityChicago

YQB - ORD

YQBORD

Québec City

Thu 4/6

2:24 p.m.-4:29 p.m.

Nonstop3h 05m

Chicago O'Hare Intl

Mon 8/6

5:00 a.m.-3:20 p.m.

1 stop9h 20m

C$ 592

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$ 295. 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$ 353.

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$ 664. 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$ 1,061.

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$ 651. 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$ 1,123 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$ 391 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$ 267 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$ 179

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$ 179. The best round-trip flight deal from Canada to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 442.
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$ 121Free CancellationRating
7.1
10,697 reviews
Search Air Canada flights
DeltaPriceFrom C$ 145Free CancellationRating
7.9
8,173 reviews
Search Delta flights
American AirlinesPriceFrom C$ 169Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights
WestJetPriceFrom C$ 173Free CancellationRating
7.2
3,255 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 177Free CancellationRating
7.4
9,255 reviews
Search United Airlines flights
Porter AirlinesPriceFrom C$ 220Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
Alaska AirlinesPriceFrom C$ 383Free CancellationRating
8.0
11,851 reviews
Search Alaska 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
Great Lakes
Hammond
Harvey
Wheeling
Naperville
Glenview
Des Plaines
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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