$147+ Cheap flights from Pearson Intl (YYZ) 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Pearson Intl to Chicago 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.The best prices from Toronto Pearson Intl to Chicago are usually found in April or July, booked 84 days in advance, depart on a Wednesday or Thursday and return on a Wednesday
Cheap flight deals from Pearson Intl to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $238 (American Airlines) |
One-way from | $147 (Mytrip) |
Popular in | December |
Cheapest in | April |
Average price | $285 |
Find flight deals from Pearson Intl to Chicago
Cheapest flights from Pearson Intl to ChicagoExplore the most affordable flight options available from Pearson Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.
Explore the most affordable flight options available from Pearson Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.
This American Airlines deal was found by Cheapflights users on 1/21. 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 American 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 1/20. 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 deal was found by Cheapflights users on 1/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com 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 1/20. 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 FlightHub deal was found by Cheapflights users on 1/20. 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 Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com 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 1/20. 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 Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flights from Pearson Intl to Chicago within your budget
Customize your flight search to find flights from Pearson Intl to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 3/3
11:31 am-12:31 pm
Nonstop2h 00m
Chicago O'Hare Intl
Mon 3/10
3:00 pm-5:30 pm
Nonstop1h 30m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 2/21
6:52 am-8:01 am
Nonstop2h 09m
Chicago O'Hare Intl
Sun 2/23
9:12 pm-11:59 pm
Nonstop1h 47m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 2/12
6:40 pm-7:37 pm
Nonstop1h 57m
Chicago O'Hare Intl
Sat 2/22
9:50 am-12:25 pm
Nonstop1h 35m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 2/13
6:00 am-9:16 am
1 stop4h 16m
Chicago O'Hare Intl
Sat 2/15
4:58 pm-10:49 pm
1 stop4h 51m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Thu 2/13
6:00 am-8:51 am
1 stop3h 51m
Chicago Midway
Sun 2/16
9:33 am-4:09 pm
1 stop5h 36m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Thu 2/13
6:00 am-8:51 am
1 stop3h 51m
Chicago Midway
Sun 2/16
9:33 am-4:09 pm
1 stop5h 36m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 2/13
6:30 am-11:30 am
1 stop6h 00m
Chicago O'Hare Intl
Mon 2/17
6:15 am-1:44 pm
1 stop6h 29m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Fri 2/21
6:30 am-5:43 pm
1 stop12h 13m
Chicago Midway
Mon 2/24
1:26 pm-11:07 pm
1 stop8h 41m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 2/13
9:00 am-10:04 am
Nonstop2h 04m
Chicago O'Hare Intl
Sun 2/16
11:04 am-1:42 pm
Nonstop1h 38m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 2/13
9:00 am-10:04 am
Nonstop2h 04m
Chicago O'Hare Intl
Sun 2/16
1:04 pm-3:45 pm
Nonstop1h 41m
Compare providers for flights from Pearson Intl to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pearson Intl to Chicago in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto Pearson Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto Pearson Intl Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto Pearson Intl Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Pearson Intl to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pearson Intl with our price prediction graph.
Travel insights for flights from Pearson Intl to Chicago
Get recent, data-driven insights about flights from Pearson Intl to Chicago including ideal travel times, pricing trends, and more.
How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Pearson Intl to Chicago. Price data was last updated on January 17, 2025.
Booking 84 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Pearson Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago?
Currently, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of $245). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of $320). 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 YYZ to CHI?
Find hourly flight availability from Pearson Intl 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 21, 2025.
It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the morning. By choosing this option you can save up to 17% on the cost of your flight, compared to a flight in the afternoon.
What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to Chicago. Price data was last updated on June 30, 2024.
Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Toronto Pearson Intl Airport to Chicago
Explore weekly flight availability from Pearson Intl 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 21, 2025.
The most flights from YYZ to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
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 21, 2025.
Get a feel of what it's like to fly with Air Canada, WestJet and American Airlines from Toronto to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Entertainment
Boarding
Comfort
Overall
Food
Crew
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Related info for your journey
Find useful and relevant information for your journey from Pearson Intl to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Toronto Pearson Intl Airport?
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Alternative routes for Pearson Intl to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Pearson Intl to Chicago
Discover the top 4 airlines that operate flights from Pearson Intl 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 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$292 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$219 | Average$316 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$221 | Average$261 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$238 | Average$326 | FlexibilityNo cancel fee | On-time71% |