Cheap flights from Canada to Chicago from $96
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 7/30. 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 April is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $235. If you’re not able to fly to Chicago in April, then May is your next best option. Flight prices from Canada to Chicago during May average around $244.
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 $381. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Canada to Chicago for around $633.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Canada to Chicago during this time can be as low as $334. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $575.
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 $296 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 $247 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
What airlines fly to Chicago?
Air Canada, United Airlines and American Airlines 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 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 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 112 per day as of June 2025. The most frequent departure time is 6:00AM, with 45% of daily flights leaving in the afternoon.
How many flights depart from Canada to Chicago on average per week?
As of June 2025, there are 787 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Thu, with 16% of flights 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?
As of June 2025, there are 5 operators available to choose from for flights from Canada to Chicago.
How old do you have to be to fly from Canada to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify 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 this flight route, the most popular plane model on flight routes from Canada to Chicago is Embraer 175 (Enhanced Winglets) (16.43% of total bookings). The next most popular plane models are De Havilland (Bombardier) DHC-8-400 Dash 8Q (14.67%), Boeing 737-800 (11.00%), and Airbus A220-300 (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 $109 | Free Cancellation | Rating 7.1 9,531 reviews | |||
| PriceFrom $112 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 7.2 2,868 reviews | |||
| PriceFrom $167 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $169 | Free Cancellation | Rating 8.0 288 reviews |
Traveling 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?
Finding the right flight to Chicago from Canada is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Canada to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Canada on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Canada to Chicago?
momondo helps you find the best flight between Canada and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Canada to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Canada to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.