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 14/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
23 Jul — 30 Jul1
Return
1 adult
Economy
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in June or April, booked 52 days in advance, depart on a Monday or Thursday and return on a Friday
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 18 July 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 18 July 2025.
Fri 31/1008:55YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 2/1121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 16/7£119
Thu 4/907:30YYZ - ORD
1 stop5h 09mMultiple Airlines
Sun 7/920:25ORD - YYZ
Nonstop1h 43mMultiple Airlines
Deal found 16/7£140
Fri 3/1014:10YYZ - ORD
Nonstop1h 54mAir Canada
Mon 6/1018:20ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 18/7£148
Wed 10/917:00YYZ - ORD
1 stop6h 20mDelta
Fri 12/909:10ORD - YYZ
1 stop5h 12mDelta
Deal found 16/7£159
Sun 12/1015:25YTZ - ORD
1 stop5h 57mAir Canada
Sat 18/1008:40ORD - YTZ
1 stop5h 05mAir Canada
Deal found 16/7£167
Mon 25/806:00YYZ - ORD
1 stop17h 59mAmerican Airlines
Wed 27/809:50ORD - YYZ
1 stop4h 46mAmerican Airlines
Deal found 16/7£193
Thu 7/817:15YTZ - ORD
2 stops14h 49mMultiple Airlines
Wed 13/808:40ORD - YTZ
1 stop5h 06mMultiple Airlines
Deal found 17/7£245
Wed 23/706:00YHM - ORD
2 stops33h 13mMultiple Airlines
Fri 25/715:18ORD - YHM
3 stops32h 23mMultiple Airlines
Deal found 15/7£427
Best flights from Toronto to Chicago
Discover carefully curated flight deals from Toronto to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 18 July 2025.
Fri 31/1008:55YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 2/1121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 16/7£119
Thu 4/907:30YYZ - ORD
1 stop5h 09mMultiple Airlines
Sun 7/920:25ORD - YYZ
Nonstop1h 43mMultiple Airlines
Deal found 16/7£140
Fri 3/1014:10YYZ - ORD
Nonstop1h 54mAir Canada
Mon 6/1018:20ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 18/7£148
Wed 10/917:00YYZ - ORD
1 stop6h 20mDelta
Fri 12/909:10ORD - YYZ
1 stop5h 12mDelta
Deal found 16/7£159
Mon 25/806:00YYZ - ORD
1 stop17h 59mAmerican Airlines
Wed 27/809:50ORD - YYZ
1 stop4h 46mAmerican Airlines
Deal found 16/7£193
Sun 12/1015:25YTZ - ORD
1 stop5h 57mAir Canada
Sat 18/1008:40ORD - YTZ
1 stop5h 05mAir Canada
Deal found 16/7£167
Thu 7/817:15YTZ - ORD
2 stops14h 49mMultiple Airlines
Wed 13/808:40ORD - YTZ
1 stop5h 06mMultiple Airlines
Deal found 17/7£245
Direct flights from Toronto to Chicago
Explore direct flight options from Toronto to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 18 July 2025.
Fri 31/1008:55YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 2/1121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 16/7£119
Fri 3/1014:10YYZ - ORD
Nonstop1h 54mAir Canada
Mon 6/1018:20ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 18/7£148
Thu 14/807:00YYZ - ORD
Nonstop1h 59mMultiple Airlines
Fri 15/820:25ORD - YYZ
Nonstop1h 45mMultiple Airlines
Deal found 18/7£174
Wed 6/806:30YYZ - ORD
Nonstop1h 56mAmerican Airlines
Thu 7/809:45ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 17/7£261
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 18 July 2025 and is based on user searches.
Wed 23/706:00YHM - ORD
2 stops33h 13mMultiple Airlines
Fri 25/715:18ORD - YHM
3 stops32h 23mMultiple Airlines
Deal found 15/7£427
Wed 23/709:00YYZ - ORD
Nonstop1h 59mMultiple Airlines
Wed 30/707:15ORD - YYZ
1 stop6h 20mMultiple Airlines
Deal found 18/7£436
Fri 25/709:00YYZ - ORD
Nonstop1h 59mUnited Airlines
Mon 28/721:31ORD - YYZ
1 stop11h 33mUnited Airlines
Deal found 15/7£300
Sat 26/700:30YYZ - ORD
1 stop12h 26mAir Canada
Fri 1/820:25ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 17/7£365
Sun 27/706:00YYZ - ORD
1 stop5h 37mAmerican Airlines
Fri 1/820:55ORD - YYZ
1 stop12h 25mAmerican Airlines
Deal found 17/7£265
Sun 27/708:50YTZ - ORD
1 stop4h 06mAir Canada
Fri 1/814:07ORD - YTZ
1 stop6h 24mAir Canada
Deal found 17/7£345
Mon 28/712:16YYZ - ORD
1 stop6h 51mDelta
Wed 6/809:00ORD - YYZ
1 stop7h 15mDelta
Deal found 16/7£283
Mon 28/707:45YYZ - ORD
1 stop7h 34mWestJet
Wed 6/806:00ORD - YYZ
1 stop4h 59mWestJet
Deal found 16/7£283
Thu 7/806:15YYZ - ORD
1 stop4h 31mAir Canada
Wed 13/820:25ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 18/7£184
Thu 7/808:25YTZ - ORD
1 stop7h 30mAir Canada
Wed 13/808:40ORD - YTZ
1 stop7h 06mAir Canada
Deal found 17/7£216
Thu 7/817:15YTZ - ORD
2 stops14h 49mMultiple Airlines
Wed 13/808:40ORD - YTZ
1 stop5h 06mMultiple Airlines
Deal found 17/7£245
Fri 22/812:14YYZ - ORD
1 stop4h 59mWestJet
Fri 22/819:59ORD - YYZ
1 stop13h 24mWestJet
Deal found 17/7£206
One-way flights from Toronto to Chicago
Search for one-way flight options from Toronto to Chicago. Find affordable one-way fares based on user searches. Data last updated 18 July 2025.
Sun 14/907:00YYZ - ORD
Nonstop1h 59mUnited Airlines
Deal found 16/7£83
Sat 16/806:20YYZ - ORD
1 stop9h 42mDelta
Deal found 17/7£107
Wed 14/114:30YYZ - ORD
1 stop8h 05mWestJet
Deal found 17/7£125
Fri 12/906:00YHM - ORD
1 stop11h 43mWestJet
Deal found 17/7£228
Cheapflights Fare Finder
Customise your flight search to find flights from Toronto 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 858,174 searches. Data last updated 18 July 2025.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.
Fly from
Toronto
Fly to
Chicago
Route
Depart
Return
Price
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 31/10
08:55-10:00
Nonstop2h 05m
Chicago O'Hare Intl
Sun 2/11
21:20-23:59
Nonstop1h 39m
£119
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 4/9
07:30-11:39
1 stop5h 09m
Chicago O'Hare Intl
Sun 7/9
20:25-23:08
Nonstop1h 43m
£140
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 3/10
14:10-15:04
Nonstop1h 54m
Chicago O'Hare Intl
Mon 6/10
18:20-21:02
Nonstop1h 42m
£148
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 10/9
17:00-22:20
1 stop6h 20m
Chicago O'Hare Intl
Fri 12/9
09:10-15:22
1 stop5h 12m
£159
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Sun 12/10
15:25-20:22
1 stop5h 57m
Chicago O'Hare Intl
Sat 18/10
08:40-14:45
1 stop5h 05m
£167
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 25/8
06:00-22:59
1 stop17h 59m
Chicago O'Hare Intl
Wed 27/8
09:50-15:36
1 stop4h 46m
£193
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Thu 7/8
17:15-07:04
2 stops14h 49m
Chicago O'Hare Intl
Wed 13/8
08:40-14:46
1 stop5h 06m
£245
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 14/9
07:00-07:59
Nonstop1h 59m
£83
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 16/8
06:20-15:02
1 stop9h 42m
£107
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 14/1
14:30-21:35
1 stop8h 05m
£125
Flights are sorted by cheapest return flights first.
Deals found on 16/7
Showing 1-10 of 11 results
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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.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
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 11 July 2025.
Booking 52 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 18 July 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 65% 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 13 July 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 18 July 2025.
The most flights from YTO to CHI are scheduled on a Thursday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 on average).
How much does it cost for a return flight from Toronto to Chicago?
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 18 July 2025.
Get a feel of what it's like to fly with Delta, United Airlines, andAmerican Airlines from Toronto to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
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.
What are the cheapest airlines flying from Toronto to Chicago round-trip?
Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at £119. Additional return tickets that might be worth considering are offered by Air Canada and Delta, with the lowest prices starting at £148 and £159, respectively. United Airlines is 39% cheaper than the average price of flights available within the next 90 days to this destination.
What are the cheapest airlines to fly from Toronto to Chicago one-way?
The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as £83. However, be on the lookout for offers from Delta and WestJet, as they are both options that can get you from Toronto to Chicago for a low price.
What are the most popular routes from Toronto to Chicago?
Most travelers choose Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago O'Hare Intl or Hamilton - Chicago O'Hare Intl when deciding on the best route from Toronto to Chicago.
What are the most reliable airlines from Toronto to Chicago?
The top 3 most reliable airlines when flying from Toronto to Chicago are Cathay Pacific (100%), SkyWest Airlines (91%) and Egyptair (90%).
What are the cheapest flights from Toronto to Chicago?
Looking at all options, your cheapest flight can be booked for £78. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £150 on average our data indicates £266 when flying from Toronto to Chicago.
Can I find deals for business class flights from Toronto to Chicago?
Yes. Cheapflights offers flight deals from Toronto to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
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.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 18 July 2025.
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 18 July 2025.
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.
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