Cheap flights from Chicago to Canada from $48
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Canada departing on 10/15. 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 Chicago to Canada
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 Canada?
If you aren’t able to travel during the month of July, then book flights to Canada from Chicago during April instead. Flights to Canada in April, while not as cheap as those in July, still average around $271.
What is the cheapest day to depart on your flight to Canada?
Our data shows that Friday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $627. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Canada for around $772.
What is the cheapest time of day to depart on your flight to Canada?
In the morning is the cheapest time of day to fly from Chicago to Canada when you can find flight prices for as low as $568. Flying to Canada in the morning is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Canada is in the afternoon when prices are around $764.
What is the cheapest Chicago to Canada flight route?
Fly from Chicago Midway to Toronto Island for the best Chicago - Canada flight prices
How far in advance should I book a flight to Canada?
You are more likely to see cheaper flights to Canada from Chicago when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Canada for around $318 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Canada from Chicago for as low as $166 on momondo.
What cabin class options are available on Chicago to Canada flights?
There are 4 cabin classes available to choose from on Chicago to Canada 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 Chicago to Canada?
Air Canada, WestJet, and Porter Airlines are the most popular carriers operating from Chicago to Canada
What airlines fly to Canada?
Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Canada from Chicago according to our data. Air Canada is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Canada. Keep in mind that there are 7 different airlines that fly to Canada on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Canada on average per day?
As of June 2025, there are 119 flights per day flying from Chicago to Canada. The most common time of day flights depart is 8:00PM, with 38% of flights taking off in the afternoon.
How many flights depart from Chicago to Canada on average per week?
The number of flights available between Chicago and Canada is 833 per week as of June 2025. The most frequent departure day is Sun, with 15% of weekly flights leaving on this day.
Cheap Chicago to Canada flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Canada
When did momondo last update prices for flights from Chicago to Canada?
Prices for flights from Chicago to Canada are updated daily.
How many operators does momondo search for flights from Chicago to Canada?
There are 7 operators available for flights from Chicago to Canada as of June 2025.
How old do you have to be to fly from Chicago to Canada?
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 Chicago to Canada.
What documentation or ID do you need to fly to Canada?
The necessary travel and health documents for your Canada 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 Chicago to Canada?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Canada is Embraer 175 (Enhanced Winglets), representing 16.39% of all bookings. The subsequent popular models are De Havilland (Bombardier) DHC-8-400 Dash 8Q at 9.65%, Embraer 175 at 9.65%, and Boeing 737-800 at 8.74%.
Best airlines flying from Chicago to Canada
Compare and see reviews for airlines that fly from Chicago to Canada with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $92 | Free Cancellation | Rating 7.4 8,801 reviews | |||
| PriceFrom $98 | Free Cancellation | Rating 7.1 9,554 reviews | |||
| PriceFrom $109 | Free Cancellation | Rating 8.0 289 reviews | |||
| PriceFrom $124 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $135 | Free Cancellation | Rating 7.2 2,873 reviews | |||
| PriceFrom $160 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $438 | Free Cancellation | Rating 8.0 10,000 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Canada?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Canada for you.
Can I find flights from Chicago to Canada with flexible booking policies on momondo?
All flight searches from Chicago to Canada on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Canada?
momondo provides multiple filters to help you find the best flight to Canada from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Canada right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Canada flights. All you need is a valid email address and we will do the rest; it is that quick and easy.