Cheap flights from Chicago to Canada from C$ 81
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 22/9. 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?
In general, July is the cheapest month to fly from Chicago to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 366. If you’re not able to fly to Canada in July, then April is your next best option. Flight prices from Chicago to Canada during April average around C$ 371.
What is the cheapest day to depart on your flight to Canada?
Our data shows that Saturday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 390. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 538. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.
What is the cheapest time of day to depart on your flight to Canada?
According to our data, the cheapest time of day to fly to Canada is in the evening. momondo users have found flights departing from Chicago to Canada in the evening for as low as C$ 401. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 468 per ticket.
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 C$ 435 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 C$ 227 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, United Airlines, and WestJet are the most popular carriers operating from Chicago to Canada
Which airlines fly to Canada?
Air Canada, United Airlines and WestJet 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 59% of people opting to fly with this airline when travelling to Canada. Keep in mind that there are 3 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?
107 flights are operational daily from Chicago to Canada as of June 2025. The most popular departure time for this route is 8:00p.m., with 37% of flights per day taking off in the afternoon.
How many flights depart from Chicago to Canada on average per week?
As of June 2025, 755 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off 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 refresh daily.
How many operators does momondo search for flights from Chicago to Canada?
The number of operators available for flights from Chicago to Canada is 3 as of June 2025.
How old do you have to be to fly from Chicago to Canada?
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 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Canada is Embraer 175 (Enhanced Winglets) (16.20% of total bookings). The next most popular plane models are Embraer 175 (9.17%), De Havilland (Bombardier) DHC-8-400 Dash 8Q (9.14%), and Boeing 737-800 (8.59%).
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 C$ 126 | Free Cancellation | Rating 7.1 9,537 reviews | |||
| PriceFrom C$ 142 | Free Cancellation | Rating 7.2 2,868 reviews | |||
| PriceFrom C$ 211 | Free Cancellation | Rating 7.4 8,790 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Canada?
It is quick and easy to find Chicago to Canada flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Canada that suits you.
Can I find flights from Chicago to Canada with flexible booking policies on momondo?
momondo does allow users to show only those flights to Canada from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Canada?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Canada from Chicago.
I’m not ready to book a flight from Chicago to Canada right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Canada 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.