Cheap flights from Canada to Chicago from C$ 160
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 5/6. 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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Recent round-trip flight deals from Canada to Chicago
These are some of the best round-trip flight deals from Canada to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.
Recent one-way flight deals from Canada to Chicago
Flying one-way? These are some of the best deals recently discovered on momondo for flights from Canada to Chicago.
Recent last minute flight deals from Canada to Chicago
Planning a quick getaway from Canada to Chicago? These are the last-minute flight deals available now.
Recent direct flight deals from Canada to Chicago
If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.
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![WestJet]()
30 May![WestJet]()
31 May
YYZ1:25 p.m.Toronto Pearson Intl
8h 55m
1 stop
ORD9:20 p.m.Chicago O'Hare Intl
ORD11:05 a.m.Chicago O'Hare Intl
11h 50m
1 stop
YYZ11:55 p.m.Toronto Pearson Intl
WestJet![WestJet]()
10 Jun![WestJet]()
24 Jun
YYC12:15 p.m.Calgary
3h 29m
ORD4:44 p.m.Chicago O'Hare Intl
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
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]()
30 May![Air Canada]()
31 May
YYZ2:10 p.m.Toronto Pearson Intl
1h 55m
ORD3:05 p.m.Chicago O'Hare Intl
ORD8:25 p.m.Chicago O'Hare Intl
1h 42m
YYZ11:07 p.m.Toronto Pearson Intl
Air Canada![Air Canada]()
30 May![Air Canada]()
31 May
YYZ7:55 a.m.Toronto Pearson Intl
1h 55m
ORD8:50 a.m.Chicago O'Hare Intl
ORD8:40 a.m.Chicago O'Hare Intl
5h 54m
1 stop
YYZ3:34 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
Prices
Airlines
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$ 384. 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$ 387.
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$ 878. 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$ 1,397.
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$ 585. 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$ 1,604 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 Winnipeg 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 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 418 when searching 16 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$ 363 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?
Air Canada, WestJet, and American 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 64% 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 April 2025, 78 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 April 2025, there are 547 flights per week flying from Canada to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Wed, with 20% 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 April 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) (15.35% of total bookings). The next most popular plane models are De Havilland (Bombardier) DHC-8-400 Dash 8Q (9.48%), Boeing 737 MAX 8 (8.21%), and Boeing 737-800 (7.51%).
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$ 146 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom C$ 154 | Free Cancellation | Rating 7.0 9,245 reviews | |||
| PriceFrom C$ 170 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom C$ 178 | Free Cancellation | Rating 7.2 2,826 reviews | |||
| PriceFrom C$ 242 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom C$ 275 | Free Cancellation | Rating 8.0 285 reviews | |||
| PriceFrom C$ 359 | Free Cancellation | Rating 8.0 9,968 reviews |
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Lisle
Glenview
Schaumburg
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Wheeling
Naperville
Great Lakes
Munster
Des Plaines
Benton Harbor
Merrillville
Harvard
Oak Brook
Elmhurst
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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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