Cheap flights from Chicago to Canada from $64
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 4/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
Deals available from 900+ travel sites.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Canada
Cheap round-trip flights
These are some of the best round-trip flight deals from Chicago to Canada that have been recently found on momondo from popular airlines, departing in the coming months.
Cheap one-way flights
Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Canada.
Cheap last minute flights
Planning a quick getaway from Chicago to Canada? These are the last-minute flight deals available now.
Cheap direct flights
If you prefer a non-stop journey, check out our latest direct flight deals to Canada, so you can enjoy a seamless trip without layovers.
Cheap bus & train deals from Chicago to Canada
Find recent round-trip train or bus tickets from Chicago to Canada.
All round-trip flight deals from Chicago to Canada
The cheapest plane tickets from Chicago to Canada found on KAYAK recently.
Air Canada flights from Chicago to Canada
Our best Air Canada deals on Chicago to Canada flight tickets
Air Canada![Air Canada]()
Feb 8![Air Canada]()
Feb 11
ORD2:05 pmChicago O'Hare Intl
8h 13m
1 stop
YYC9:18 pmCalgary
YYC8:30 amCalgary
9h 08m
1 stop
ORD6:38 pmChicago O'Hare Intl
Air Canada![Air Canada]()
Jul 14![Air Canada]()
Jul 19
ORD2:40 pmChicago O'Hare Intl
9h 23m
1 stop
YYC11:03 pmCalgary
YYC6:00 amCalgary
7h 54m
1 stop
ORD2:54 pmChicago O'Hare Intl
American Airlines flights from Chicago to Canada
Our best American Airlines deals on Chicago to Canada flight tickets
American Airlines![American Airlines]()
Feb 14![American Airlines]()
Feb 18
ORD3:00 pmChicago O'Hare Intl
1h 30m
YYZ5:30 pmToronto Pearson Intl
YYZ6:15 amToronto Pearson Intl
2h 15m
ORD7:30 amChicago O'Hare Intl
American Airlines![American Airlines]()
Feb 13![American Airlines]()
Feb 18
ORD8:11 amChicago O'Hare Intl
1h 40m
YYZ10:51 amToronto Pearson Intl
YYZ6:15 amToronto Pearson Intl
2h 15m
ORD7:30 amChicago O'Hare Intl
See travel insights to Canada from
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
Prices
Airlines
Other information
What is the cheapest month to fly to Canada?
If you aren’t able to travel during the month of April, then book flights to Canada from Chicago during February instead. Flights to Canada in February, while not as cheap as those in April, still average around $277.
What is the cheapest day to depart on your flight to Canada?
Our data shows that Tuesday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $292. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Canada for around $311.
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 $563. 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 $736.
What is the cheapest Chicago to Canada flight route?
Fly from Chicago O'Hare Intl to Calgary 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 21 weeks ahead of your departure date. In general, you can expect to find flights to Canada for around $307 when searching 21 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 $197 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?
WestJet, United Airlines, 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 41% 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 January 2025, there are 69 flights per day flying from Chicago to Canada. The most common time of day flights depart is 6:00PM, with 48% 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 488 per week as of January 2025. The most frequent departure day is Mon, with 16% 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 January 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 Boeing 737-800, representing 12.99% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 10.46%, Boeing 777-300ER at 9.57%, and Embraer 170 at 7.31%.
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 $116 | Free Cancellation | Rating 7.0 8,635 reviews | |||
| PriceFrom $122 | Free Cancellation | Rating 7.9 277 reviews | |||
| PriceFrom $122 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $125 | Free Cancellation | Rating 7.2 2,829 reviews | |||
| PriceFrom $148 | Free Cancellation | Rating 7.4 8,985 reviews | |||
| PriceFrom $148 | Free Cancellation | Rating 8.0 8,521 reviews | |||
| PriceFrom $154 | Free Cancellation | Rating 8.0 9,706 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.
Get notified when prices go down
Daily price changes in your inbox - only with Price Alerts.
From?
To?
Email me momondo's favorite deals
By creating a price alert you accept our terms of use and privacy policy.
Find better results for your trip to Canada
Popular cities in Canada
Popular flights according to clicks in the last 7 days on momondo
Flights to Torontofrom $93
Flights to Vancouverfrom $80
Flights to Montrealfrom $99
Flights to Calgaryfrom $77
Flights to Ottawafrom $162
Flights to Halifaxfrom $151
Flights to Winnipegfrom $176
Flights to Québec Cityfrom $265
Flights to Saskatoonfrom $186
Flights to Kelownafrom $141
Flights to Reginafrom $195
Flights to St. John'sfrom $234