$67+ Cheap flights from Chicago (CHI) to Canada
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Canada with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Canada
Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated January 15, 2026.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $168 (Flightnetwork) |
One-way from | $67 (oojo) |
Popular in | January |
Cheapest in | September |
Average price | $309 |
Good round-trip deal | $214 or less |
Good one-way deal | $88 or less |
Find flight deals from Chicago to Canada
Cheapest flights from Chicago to CanadaExplore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.
Explore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.
This Flightnetwork deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This FlightHub deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Use the filters below to find and compare flights from Chicago to Canada that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Wed 2/11
11:00 am-1:42 pm
Nonstop1h 42m
Toronto Island
Sun 2/15
9:15 am-10:05 am
Nonstop1h 50m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Wed 2/11
11:00 am-1:42 pm
Nonstop1h 42m
Toronto Island
Tue 2/17
9:15 am-10:05 am
Nonstop1h 50m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 2/6
11:05 am-1:47 pm
Nonstop1h 42m
Toronto Island
Mon 2/9
9:20 am-10:10 am
Nonstop1h 50m
ChicagoMontreal
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Sun 2/8
10:35 am-2:00 pm
Nonstop2h 25m
Montreal Pierre Elliott Trudeau Intl
Wed 2/11
4:45 pm-6:51 pm
Nonstop3h 06m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 1/29
11:05 am-1:47 pm
Nonstop1h 42m
Toronto Island
Tue 2/3
9:15 am-10:05 am
Nonstop1h 50m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 1/29
11:00 am-1:42 pm
Nonstop1h 42m
Toronto Island
Mon 2/2
9:15 am-10:05 am
Nonstop1h 50m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 3/17
4:15 pm-6:57 pm
Nonstop1h 42m
Toronto Island
Wed 4/1
9:15 am-10:05 am
Nonstop1h 50m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 2/12
11:05 am-1:47 pm
Nonstop1h 42m
Toronto Island
Thu 2/19
9:20 am-10:10 am
Nonstop1h 50m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 3/20
4:15 pm-6:57 pm
Nonstop1h 42m
Toronto Island
Wed 4/1
2:30 pm-3:20 pm
Nonstop1h 50m
ChicagoCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Wed 4/8
12:55 pm-9:48 pm
1 stop9h 53m
Calgary
Mon 4/13
1:27 pm-12:29 am
1 stop10h 02m
Best time to book a flight from Chicago to Canada
Have a flexible travel schedule? Discover the best time to fly to Canada from Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Canada
What is the cheapest month to book a flight from Chicago to Canada?
Currently, March is the cheapest month in which you can book a flight from Chicago to Canada (average of $79). Flying from Chicago to Canada in December is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to CA?
Find hourly flight availability from Chicago to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 15, 2026.
When flying from Chicago to Canada, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 9% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago to Canada?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Canada. Price data was last updated on January 10, 2026.
Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Monday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Canada
Explore weekly flight availability from Chicago to Canada. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 15, 2026.
The most flights from CHI to CA0 are scheduled on a Thursday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (37 on average).
How often are flights from Chicago to Canada delayed?
About 18% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 136 minutes.
What is the most punctual flight time for Chicago to Canada flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Canada flights?
Over the last year, Korean Air have had the lowest number of delays on this route, with just 11% of flights being delayed.
Reviews of airlines servicing Canada
Get insights into the airlines that provide service to Canada. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Canada. Reviews last updated January 15, 2026.
Peruse reviews from past customers who have flown with Porter Airlines, United Airlines, and American Airlines from Chicago to Canada to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Overall
Entertainment
Food
Boarding
Crew
Reviews
Mohameed,Nov 2025
LAS - YYZ
Comfort
Overall
Entertainment
Food
Boarding
Crew
Reviews
Mohameed,Nov 2025
LAS - YYZ
Comfort
Overall
Entertainment
Food
Boarding
Crew
Reviews
Mohameed,Nov 2025
LAS - YYZ
Comfort
Overall
Entertainment
Food
Boarding
Crew
Reviews
Mohameed,Nov 2025
LAS - YYZ
Comfort
Overall
Entertainment
Food
Boarding
Crew
Reviews
Mohameed,Nov 2025
LAS - YYZ
Comfort
Overall
Entertainment
Food
Boarding
Crew
Reviews
Mohameed,Nov 2025
LAS - YYZ
Related info for your journey
Find useful and relevant information for your journey from Chicago to Canada. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chicago to Canada
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chicago to Canada
Discover the top 7 airlines that operate flights from Chicago to Canada. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$433 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$80 | Average$379 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$105 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$327 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$172 | Average$348 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$192 | Average$457 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$705 | FlexibilityNo cancel fee | On-time75% |