$99+ Cheap flights from Canada to Chicago (CHI)
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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
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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
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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 Canada to Chicago
Cheapest flights from Canada to ChicagoExplore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.
Explore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.
This oojo deal was found by Cheapflights users on 1/25. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 1/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This oojo deal was found by Cheapflights users on 1/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 1/27. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 1/25. 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 United Airlines 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 1/25. 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.
This Ticket deal was found by Cheapflights users on 1/26. 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 Ticket 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 1/26. 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 United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 1/27. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 1/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This SmartFares deal was found by Cheapflights users on 1/26. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flight deals from Canada to Chicago
Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated January 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $180 (oojo) |
One-way from | $99 (Kiwi.com) |
Popular in | January |
Cheapest in | July |
Average price | $293 |
Good round-trip deal | $185 or less |
Good one-way deal | $122 or less |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Canada to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Thu 3/26
9:25 am-11:18 am
Nonstop2h 53m
Chicago O'Hare Intl
Mon 3/30
12:50 pm-4:05 pm
Nonstop2h 15m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 3/12
9:15 am-10:05 am
Nonstop1h 50m
Chicago Midway
Thu 3/19
4:15 pm-6:57 pm
Nonstop1h 42m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 5/6
8:50 am-9:50 am
Nonstop2h 00m
Chicago O'Hare Intl
Sat 5/9
9:15 pm-11:59 pm
Nonstop1h 44m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 5/20
8:50 am-9:40 am
Nonstop1h 50m
Chicago Midway
Mon 5/25
5:35 pm-8:15 pm
Nonstop1h 40m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Tue 3/10
7:00 am-11:18 am
1 stop5h 18m
Chicago O'Hare Intl
Tue 3/31
12:50 pm-7:52 pm
1 stop6h 02m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 2/17
9:00 pm-10:04 pm
Nonstop2h 04m
Chicago O'Hare Intl
Tue 2/24
2:30 pm-9:24 pm
1 stop5h 54m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 2/19
9:20 am-10:10 am
Nonstop1h 50m
Chicago Midway
Mon 2/23
11:05 am-1:47 pm
Nonstop1h 42m
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Tue 6/2
10:35 am-4:50 pm
1 stop7h 15m
Chicago Midway
Fri 6/5
10:25 am-5:15 pm
1 stop5h 50m
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Tue 6/2
6:30 am-9:40 am
1 stop4h 10m
Chicago Midway
Thu 6/4
10:25 am-5:15 pm
1 stop5h 50m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 6/6
2:50 pm-11:12 pm
1 stop9h 22m
Chicago O'Hare Intl
Tue 6/9
3:00 pm-5:58 pm
Nonstop1h 58m
Best time to book a flight from Canada to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Canada to Chicago
What is the cheapest month to book a flight from Canada to Chicago?
Currently, April is the cheapest month in which you can book a flight from Canada to Chicago (average of $82). Flying from Canada to Chicago in December is currently the most expensive (average of $136). 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 CA to CHI?
Find hourly flight availability from Canada to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 27, 2026.
A simple way to save on the total cost of your ticket is to fly from Canada to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the evening.
What is the cheapest day to fly from Canada to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Canada to Chicago. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Thursday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Canada to Chicago
Explore weekly flight availability from Canada to Chicago. 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 27, 2026.
The most flights from CA0 to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 on average).
How often are flights from Canada to Chicago delayed?
About 12% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 138 minutes.
What is the most punctual flight time for Canada to Chicago flights?
Historically, flights departing at night 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 Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Canada to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated January 27, 2026.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
Overall
Boarding
Food
Entertainment
Comfort
Reviews
Mohameed,Nov 2025
LAS - YYZ
Crew
Overall
Boarding
Food
Entertainment
Comfort
Reviews
Mohameed,Nov 2025
LAS - YYZ
Crew
Overall
Boarding
Food
Entertainment
Comfort
Reviews
Mohameed,Nov 2025
LAS - YYZ
Crew
Overall
Boarding
Food
Entertainment
Comfort
Reviews
Mohameed,Nov 2025
LAS - YYZ
Crew
Overall
Boarding
Food
Entertainment
Comfort
Reviews
Mohameed,Nov 2025
LAS - YYZ
Crew
Overall
Boarding
Food
Entertainment
Comfort
Reviews
Mohameed,Nov 2025
LAS - YYZ
Related info for your journey
Find useful and relevant information for your journey from Canada to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Canada to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Canada to Chicago
Discover the top 5 airlines that operate flights from Canada to Chicago. 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$303 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$83 | Average$400 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$90 | Average$399 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$237 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$167 | Average$371 | FlexibilityNo cancel fee | On-time71% |