$142+ Cheap flights from Toronto Island (YTZ) 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Toronto Island 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.Cheap flight deals from Toronto Island to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) 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 17, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $236 (Trip.com) |
One-way from | $145 (Justfly.com) |
Popular in | January |
Cheapest in | December |
Average price | $363 |
Find flight deals from Toronto Island to Chicago
Cheapest flights from Toronto Island to ChicagoExplore the most affordable flight options available from Toronto Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 17, 2025.
Explore the most affordable flight options available from Toronto Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 17, 2025.
This Trip.com deal was found by Cheapflights users on 1/15. 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 Booking.com deal was found by Cheapflights users on 1/16. 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 Air Canada deal was found by Cheapflights users on 1/15. 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 Mytrip deal was found by Cheapflights users on 1/16. 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 1/15. 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.
Find flights from Toronto Island to Chicago within your budget
Customize your flight search to find flights from Toronto Island 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 17, 2025.
Fly from
Fly to
Route
Depart
Return
Price
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 2/14
11:20 am-12:10 pm
Nonstop1h 50m
Chicago Midway
Mon 2/17
1:05 pm-3:47 pm
Nonstop1h 42m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Fri 2/7
3:25 pm-7:55 pm
1 stop5h 30m
Chicago O'Hare Intl
Sun 2/9
7:20 am-2:50 pm
1 stop6h 30m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 2/20
11:20 am-12:10 pm
Nonstop1h 50m
Chicago Midway
Sun 2/23
1:05 pm-3:47 pm
Nonstop1h 42m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Thu 2/6
1:05 pm-9:39 am
2 stops21h 34m
Chicago O'Hare Intl
Sun 2/9
5:35 am-8:05 pm
2 stops13h 30m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 2/21
11:20 am-5:33 pm
1 stop7h 13m
Chicago Midway
Sun 2/23
1:05 pm-3:47 pm
Nonstop1h 42m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 3/29
11:10 am-12:00 pm
Nonstop1h 50m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Thu 2/6
10:25 am-2:45 pm
1 stop5h 20m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Wed 1/29
11:55 am-10:55 pm
1 stop12h 00m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 2/19
1:05 pm-11:00 pm
2 stops10h 55m
Compare providers for flights from Toronto Island 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 Toronto Island to Chicago in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Toronto Island 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 Island Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto Island Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Toronto Island 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 Island 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 Toronto Island to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto Island with our price prediction graph.
Travel insights for flights from Toronto Island to Chicago
Get recent, data-driven insights about flights from Toronto Island to Chicago including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Toronto Island Airport to Chicago?
Currently, August is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $245). Flying from Toronto Island 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 YTZ to CHI?
Find hourly flight availability from Toronto Island 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 17, 2025.
Unlike in the morning, when flights are generally more expensive, you can save up to 16% on flights from Toronto Island Airport to Chicago by exploring options for tickets at noon.
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 17, 2025.
Read reviews from past customers who have flown Air Canada and Porter Airlines from Toronto to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Related info for your journey
Find useful and relevant information for your journey from Toronto Island 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 Island Airport?
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Alternative routes for Toronto Island to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Toronto Island to Chicago
Discover the top airline that operate flights from Toronto Island 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 17, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$260 | FlexibilityNo cancel fee | On-time52% |