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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How to get the cheapest flight ticket from Canada to Chicago
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?
The month of May is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 334.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 680. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,284. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.
What is the cheapest time of day to depart on your flight to Chicago?
In the evening is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 551. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,456 per ticket.
What is the cheapest Canada to Chicago flight route?
Fly from Toronto Island to Chicago Midway for the best Canada - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Canada when booking 12 weeks ahead of your departure date. In general, you can expect to find flights to Chicago 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 from Canada for as low as C$ 338 on momondo.
What cabin class options are available on Canada to Chicago flights?
There are 4 cabin classes available to choose from on Canada to Chicago 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?
WestJet, Air Canada, and Porter Airlines are the most popular carriers operating from Canada to Chicago
Which airlines fly to Chicago?
Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago from Canada according to our data. Air Canada is the first choice among our users, with 61% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Canada to Chicago on average per day?
The number of flights available between Canada and Chicago is 120 per day as of June 2025. The most frequent departure time is 6:00a.m., with 45% of daily flights leaving in the afternoon.
How many flights depart from Canada to Chicago on average per week?
841 flights are operational weekly from Canada to Chicago as of June 2025. The most popular departure day for this route is Thu, with 16% of flights per week taking off on this day.
Cheap Canada to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago
When did momondo last update prices for flights from Canada to Chicago?
Prices for flights from Canada to Chicago were last updated today.
How many operators does momondo search for flights from Canada to Chicago?
The number of operators available for flights from Canada to Chicago is 7 as of June 2025.
How old do you have to be to fly from Canada to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Canada to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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 Canada to Chicago?
Based on momondo bookings for flights between Canada and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 16.43% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 14.67%, Boeing 737-800 with 11.00%, and Airbus A220-300 with 7.81%.
Best airlines flying from Canada to Chicago
Compare and see reviews for airlines that fly from Canada to Chicago 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?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Canada to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Canada to Chicago . Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Canada to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.
How can momondo help me find flights from Canada to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Canada to Chicago.
I’m not ready to book a flight from Canada to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Canada and alert you when they change.