Cheap flights from Toronto to Chicago from £83
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 19/10. Fares are subject to change and may not be available on all flights or dates of travel.
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 85 days in advance, depart on a Thursday or Friday and return on a Thursday
Cheap flight deals from Toronto to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) 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 3 September 2025.
Round-trip from | £109 |
---|---|
One-way from | £83 |
Popular in | December |
Cheapest in | July |
Average price | £186 |
Good round-trip deal | £524 or less |
Good one-way deal | £345 or less |
Find flight deals from Toronto to Chicago
Cheapest flights from Toronto to ChicagoExplore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 September 2025.
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 September 2025.
Cheapflights Fare Finder
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 14/11
06:52-07:58
Nonstop2h 06m
Chicago O'Hare Intl
Sun 16/11
13:19-16:02
Nonstop1h 43m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 28/10
11:00-12:05
Nonstop2h 05m
Chicago O'Hare Intl
Sat 1/11
21:20-23:59
Nonstop1h 39m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 25/10
17:15-18:22
Nonstop2h 07m
Chicago O'Hare Intl
Sat 1/11
13:19-16:02
Nonstop1h 43m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 29/10
09:00-10:05
Nonstop2h 05m
Chicago O'Hare Intl
Sun 2/11
07:10-09:58
Nonstop1h 48m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 29/10
15:30-16:52
Nonstop2h 22m
Chicago O'Hare Intl
Sat 1/11
13:19-16:02
Nonstop1h 43m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 28/10
09:00-10:05
Nonstop2h 05m
Chicago O'Hare Intl
Sun 2/11
21:20-23:59
Nonstop1h 39m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 27/10
17:30-18:39
Nonstop2h 09m
Chicago O'Hare Intl
Sat 1/11
18:28-21:21
Nonstop1h 53m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 25/10
09:00-09:55
Nonstop1h 55m
Chicago O'Hare Intl
Sun 2/11
21:20-23:59
Nonstop1h 39m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 27/10
17:30-18:39
Nonstop2h 09m
Chicago O'Hare Intl
Sun 2/11
21:20-23:59
Nonstop1h 39m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 26/11
19:40-23:43
1 stop5h 03m
Chicago O'Hare Intl
Sat 29/11
07:10-09:58
Nonstop1h 48m
Best time to book a flight from Toronto to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Toronto to Chicago
How far ahead should I book a flight from Toronto to Chicago?
Use this chart to determine the optimal time to book a return flight from Toronto to Chicago. Price data was last updated on 29 August 2025.
Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto 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 to Chicago?
Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of £595). Flying from Toronto to Chicago in July is currently the most expensive (average of £843). 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 YTO to CHI?
Find hourly flight availability from Toronto 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 3 September 2025.
When flying from Toronto to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 48% versus a flight at midday.
What is the cheapest day to fly from Toronto to Chicago?
Use this chart to determine the cheapest time to fly return from Toronto to Chicago. Price data was last updated on 31 August 2025.
Travellers seeking maximum savings on their Toronto to Chicago flight should consider departing on Thursday mornings when fares are most often at their lowest. Saturday at midday flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Toronto to Chicago
Explore weekly flight availability from Toronto 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 3 September 2025.
The most flights from YTO to CHI are scheduled on a Tuesday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).
How much does it cost for a return flight from Toronto to Chicago?
Related info for your journey
Find useful and relevant information for your journey from Toronto to Chicago. 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 Toronto to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Toronto to Chicago
Discover the top airline that operate flights from Toronto 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 858,174 searches. Data last updated 3 September 2025.
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Toronto to Chicago?
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Toronto to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Why should you use Cheapflights to find cheap flight tickets from Toronto to Chicago?
Cheapflights simply makes it quick and affordable to book flights from Toronto to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Toronto to Chicago with no change fees?
Certainly. Search results for flights to Chicago from Toronto shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from Toronto to Chicago become cheaper?
Yes! Start tracking prices for Toronto to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.