Cheap flights from Canada to Chicago from C$ 131
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 30/7. 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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1 adult
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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![Air Canada]()
19 Sep![Air Canada]()
21 Sep
YYZ12:20 p.m.Toronto Pearson Intl
1h 54m
ORD1:14 p.m.Chicago O'Hare Intl
ORD3:50 p.m.Chicago O'Hare Intl
1h 43m
YYZ6:33 p.m.Toronto Pearson Intl
Air Canada![Air Canada]()
5 Sep![Air Canada]()
8 Sep
YUL6:40 p.m.Montreal Pierre Elliott Trudeau Intl
2h 31m
ORD8:11 p.m.Chicago O'Hare Intl
ORD10:40 a.m.Chicago O'Hare Intl
2h 14m
YUL1:54 p.m.Montreal Pierre Elliott Trudeau Intl
United Airlines flights from Canada to Chicago O'Hare Intl Airport
Our best United Airlines deals on Canada to Chicago O'Hare Intl Airport flight tickets
United Airlines![United Airlines]()
19 Sep![United Airlines]()
22 Sep
YYZ7:00 a.m.Toronto Pearson Intl
1h 59m
ORD7:59 a.m.Chicago O'Hare Intl
ORD9:31 p.m.Chicago O'Hare Intl
11h 33m
1 stop
YYZ10:04 a.m.Toronto Pearson Intl
United Airlines![United Airlines]()
4 Sep![United Airlines]()
10 Sep
YYZ2:30 p.m.Toronto Pearson Intl
6h 18m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
ORD7:15 a.m.Chicago O'Hare Intl
5h 32m
1 stop
YYZ1:47 p.m.Toronto Pearson Intl
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
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Other information
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
In general, May 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$ 360. The month of November is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Canada averaging around C$ 380.
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$ 787. 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$ 1,313.
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$ 581. 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 in the afternoon when prices are C$ 1,509 on average. Flights to Chicago O'Hare Intl Airport from Canada in the afternoon 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 Toronto Pearson Intl 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 12 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 405 when searching 12 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$ 338 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.
What is the cheapest airline that flies from Canada to Chicago O'Hare Intl?
WestJet, Air Canada, and United Airlines are the most popular carriers operating from Canada to Chicago O'Hare Intl
Which airlines fly to Chicago O'Hare Intl Airport?
Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Canada according to our data. Air Canada is the first choice among our users, with 65% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 7 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Canada to Chicago O'Hare Intl Airport on average per day?
As of June 2025, 128 flights take off from Canada and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 6:00a.m., with 45% of daily flights taking off in the afternoon.
How many flights depart from Canada to Chicago O'Hare Intl Airport on average per week?
As of June 2025, there are 899 flights per week flying from Canada to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Thu, with 16% of flights taking off on this day.
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
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?
As of June 2025, there are 7 operators available to choose from 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Canada to Chicago O'Hare Intl Airport is Embraer 175 (Enhanced Winglets) (15.86% of total bookings). The next most popular plane models are De Havilland (Bombardier) DHC-8-400 Dash 8Q (10.66%), Boeing 737-800 (10.16%), and Boeing 737 MAX 8 (7.53%).
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 | ||
|---|---|---|---|---|---|
| PriceFrom C$ 148 | Free Cancellation | Rating 7.1 9,531 reviews | |||
| PriceFrom C$ 169 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom C$ 176 | Free Cancellation | Rating 7.2 2,868 reviews | |||
| PriceFrom C$ 197 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom C$ 232 | Free Cancellation | Rating 8.0 288 reviews | |||
| PriceFrom C$ 240 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom C$ 355 | Free Cancellation | Rating 8.0 10,000 reviews |
Travelling to a place near Chicago?
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Lisle
Glenview
Skokie
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Great Lakes
Wheeling
Naperville
Munster
Des Plaines
Benton Harbor
Harvard
Merrillville
Schaumburg
Oak Brook
Elmhurst
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Rockford
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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