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 26/2. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
27 Dec — 3 Jan1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 77 days in advance, depart on a Saturday or Friday and return on a Wednesday
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 27 November 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 27 November 2025.
Tue 9/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 11/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 25/11£150
Wed 17/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 8/118:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 25/11£154
Thu 11/1215:30YYZ - ORD
Nonstop2h 22mUnited Airlines
Sun 14/1218:15ORD - YYZ
1 stop4h 31mUnited Airlines
Deal found 25/11£157
Thu 18/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Thu 8/113:13ORD - YYZ
Nonstop1h 49mUnited Airlines
Deal found 25/11£158
Tue 16/1212:15YYZ - ORD
1 stop6h 31mDelta
Tue 6/118:15ORD - YYZ
1 stop3h 26mDelta
Deal found 25/11£159
Fri 12/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Sun 14/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 24/11£161
Mon 29/1209:54YYZ - ORD
1 stop8h 28mDelta
Wed 7/112:15ORD - YYZ
1 stop7h 11mDelta
Deal found 26/11£167
Wed 10/1215:30YYZ - ORD
Nonstop2h 22mUnited Airlines
Mon 15/1218:15ORD - YYZ
1 stop4h 31mUnited Airlines
Deal found 26/11£170
Fri 12/1212:13YYZ - ORD
1 stop7h 14mDelta
Sun 14/1208:55ORD - YYZ
1 stop7h 20mDelta
Deal found 24/11£174
Thu 11/1210:00YYZ - ORD
1 stop14h 43mUnited Airlines
Mon 15/1214:24ORD - YYZ
1 stop6h 00mUnited Airlines
Deal found 25/11£175
Tue 23/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Tue 13/111:15ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 26/11£177
Tue 16/1207:30YYZ - ORD
1 stop7h 34mAmerican Airlines
Wed 17/1209:40ORD - YYZ
1 stop11h 53mAmerican Airlines
Deal found 25/11£179
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 27 November 2025.
Fri 6/215:30YYZ - ORD
Nonstop2h 10mUnited Airlines
Tue 17/208:50ORD - YYZ
1 stop4h 24mUnited Airlines
Deal found 24/11£136
Fri 9/110:25YTZ - ORD
2 stops11h 41mAir Canada
Fri 16/115:35ORD - YTZ
2 stops17h 07mAir Canada
Deal found 25/11£210
Fri 9/118:15YTZ - ORD
1 stop5h 22mMultiple Airlines
Fri 16/116:38ORD - YTZ
1 stop18h 02mMultiple Airlines
Deal found 25/11£230
Sun 8/209:00YYZ - ORD
Nonstop2h 06mUnited Airlines
Thu 19/206:00ORD - YYZ
1 stop4h 48mUnited Airlines
Deal found 24/11£136
Sun 8/221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 18/218:25ORD - YYZ
1 stop4h 21mUnited Airlines
Deal found 24/11£136
Fri 20/218:40YYZ - ORD
1 stop5h 33mUnited Airlines
Mon 23/218:25ORD - YYZ
1 stop4h 21mUnited Airlines
Deal found 25/11£137
Fri 13/314:45YYZ - ORD
1 stop9h 59mUnited Airlines
Mon 16/316:47ORD - YYZ
Nonstop1h 58mUnited Airlines
Deal found 25/11£137
Thu 19/219:40YYZ - ORD
1 stop5h 03mUnited Airlines
Sat 21/208:50ORD - YYZ
1 stop9h 07mUnited Airlines
Deal found 25/11£137
Fri 20/214:57YYZ - ORD
1 stop5h 51mUnited Airlines
Sun 1/313:02ORD - YYZ
1 stop4h 55mUnited Airlines
Deal found 26/11£137
Thu 15/115:30YYZ - ORD
Nonstop2h 10mUnited Airlines
Sun 18/108:52ORD - YYZ
1 stop4h 22mUnited Airlines
Deal found 26/11£138
Fri 9/121:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Fri 16/106:05ORD - YYZ
1 stop4h 43mUnited Airlines
Deal found 25/11£138
Wed 7/121:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Mon 12/106:05ORD - YYZ
1 stop4h 43mUnited Airlines
Deal found 26/11£138
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 27 November 2025.
Tue 3/211:00YYZ - ORD
Nonstop2h 08mUnited Airlines
Tue 17/218:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 24/11£136
Sun 8/221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Mon 16/221:14ORD - YYZ
Nonstop1h 45mUnited Airlines
Deal found 24/11£138
Thu 8/115:30YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 12/118:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 26/11£139
Tue 9/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 11/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 25/11£150
Wed 17/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 8/118:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 25/11£154
Wed 10/1209:00YYZ - ORD
Nonstop2h 02mUnited Airlines
Wed 17/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 26/11£170
Thu 19/308:55YYZ - ORD
Nonstop2h 07mUnited Airlines
Sun 22/318:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 24/11£173
Thu 25/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Fri 2/121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 26/11£183
Wed 18/308:55YYZ - ORD
Nonstop2h 07mUnited Airlines
Sun 22/318:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 25/11£195
Thu 25/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 31/1221:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 24/11£201
Mon 15/1217:30YYZ - ORD
Nonstop2h 22mUnited Airlines
Thu 25/1221:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 26/11£202
Tue 16/1218:30YYZ - ORD
Nonstop2h 00mMultiple Airlines
Wed 17/1207:10ORD - YYZ
Nonstop1h 48mMultiple Airlines
Deal found 25/11£210
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 27 November 2025 and is based on user searches.
Mon 1/1208:50YTZ - ORD
1 stop11h 05mAir Canada
Wed 3/1213:59ORD - YTZ
1 stop6h 29mAir Canada
Deal found 25/11£405
Tue 9/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 11/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 25/11£150
Wed 10/1215:30YYZ - ORD
Nonstop2h 22mUnited Airlines
Mon 15/1218:15ORD - YYZ
1 stop4h 31mUnited Airlines
Deal found 26/11£170
Thu 11/1215:30YYZ - ORD
Nonstop2h 22mUnited Airlines
Sun 14/1218:15ORD - YYZ
1 stop4h 31mUnited Airlines
Deal found 25/11£157
Fri 12/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Sun 14/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 24/11£161
Fri 12/1212:13YYZ - ORD
1 stop7h 14mDelta
Sun 14/1208:55ORD - YYZ
1 stop7h 20mDelta
Deal found 24/11£174
Tue 16/1212:15YYZ - ORD
1 stop6h 31mDelta
Tue 6/118:15ORD - YYZ
1 stop3h 26mDelta
Deal found 25/11£159
Tue 16/1207:30YYZ - ORD
1 stop7h 34mAmerican Airlines
Wed 17/1209:40ORD - YYZ
1 stop11h 53mAmerican Airlines
Deal found 25/11£179
Wed 17/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 8/108:52ORD - YYZ
1 stop4h 22mUnited Airlines
Deal found 25/11£154
Thu 18/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Wed 7/116:50ORD - YYZ
Nonstop1h 55mUnited Airlines
Deal found 25/11£158
Tue 23/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Tue 13/111:15ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 26/11£177
Mon 29/1209:54YYZ - ORD
1 stop8h 28mDelta
Wed 7/112:15ORD - YYZ
1 stop7h 11mDelta
Deal found 26/11£167
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 27 November 2025.
Thu 26/207:30YYZ - ORD
1 stop6h 45mUnited Airlines
Deal found 26/11£90
Fri 9/119:40YYZ - ORD
1 stop4h 59mUnited Airlines
Deal found 24/11£92
Sun 11/118:40YYZ - ORD
1 stop5h 19mUnited Airlines
Deal found 26/11£92
Wed 10/1209:00YYZ - ORD
Nonstop2h 02mUnited Airlines
Deal found 26/11£94
Sun 22/210:05YYZ - ORD
1 stop7h 36mDelta
Deal found 25/11£97
Sat 17/119:40YYZ - ORD
1 stop15h 14mUnited Airlines
Deal found 26/11£98
Wed 17/1212:13YYZ - ORD
1 stop5h 46mDelta
Deal found 26/11£101
Wed 17/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 25/11£105
Thu 18/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Deal found 25/11£105
Thu 25/1219:40YYZ - ORD
1 stop13h 08mUnited Airlines
Deal found 26/11£108
Wed 25/216:10YYZ - ORD
2 stops8h 33mUnited Airlines
Deal found 25/11£110
Sat 10/112:10YYZ - ORD
2 stops12h 29mUnited Airlines
Deal found 26/11£112
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 27 November 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 6/2
15:30-16:40
Nonstop2h 10m
Chicago O'Hare Intl
Tue 17/2
08:50-14:14
1 stop4h 24m
£136
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 8/2
09:00-10:06
Nonstop2h 06m
Chicago O'Hare Intl
Thu 19/2
06:00-11:48
1 stop4h 48m
£136
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 8/2
21:00-22:05
Nonstop2h 05m
Chicago O'Hare Intl
Wed 18/2
18:25-23:46
1 stop4h 21m
£136
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 20/2
18:40-23:13
1 stop5h 33m
Chicago O'Hare Intl
Mon 23/2
18:25-23:46
1 stop4h 21m
£137
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 13/3
14:45-23:44
1 stop9h 59m
Chicago O'Hare Intl
Mon 16/3
16:47-19:45
Nonstop1h 58m
£137
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 19/2
19:40-23:43
1 stop5h 03m
Chicago O'Hare Intl
Sat 21/2
08:50-18:57
1 stop9h 07m
£137
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 20/2
14:57-19:48
1 stop5h 51m
Chicago O'Hare Intl
Sun 1/3
13:02-18:57
1 stop4h 55m
£137
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 15/1
15:30-16:40
Nonstop2h 10m
Chicago O'Hare Intl
Sun 18/1
08:52-14:14
1 stop4h 22m
£138
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 9/1
21:00-22:05
Nonstop2h 05m
Chicago O'Hare Intl
Fri 16/1
06:05-11:48
1 stop4h 43m
£138
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 7/1
21:00-22:05
Nonstop2h 05m
Chicago O'Hare Intl
Mon 12/1
06:05-11:48
1 stop4h 43m
£138
Flights are sorted by cheapest return flights first.
Deals found on 24/11
Showing 1-10 of 25 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 21 November 2025.
Booking 77 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, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of £63). Flying from Toronto to Chicago in February is currently the most expensive (average of £144). 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 27 November 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 at midday, which can drop the price by up to 37% versus a flight in the evening.
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 25 November 2025.
Travellers seeking maximum savings on their Toronto to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday 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 27 November 2025.
The most flights from YTO to CHI are scheduled on a Monday (64 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (45 on average).
How much does it cost for a return flight from Toronto to Chicago?
How often are flights from Toronto to Chicago delayed?
About 11% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.
What is the most punctual flight time for Toronto 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 Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Toronto to Chicago flights?
Over the past year, Air Antilles have had the lowest number of delays on this route, with no flights being classified as 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 27 November 2025.
Get a feel of what it's like to fly with Porter 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.
It's good. Planes are new and fresh. WiFi is best and stands 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.
How long is the flight from Toronto to Chicago?
A quick flight from Toronto to Chicago can take about 2h 10m. United Airlines provides one of the quickest options available for as low as £136. Airlines will cover a distance of 436 mi. This flight may include one or multiple stops.
What is the cheapest airline to fly from Toronto to Chicago round-trip?
Flying on Air Canada is currently your cheapest option to Chicago, with prices starting at £139. Air Canada is 27% cheaper than the average price of flights available within the next 90 days to this destination.
What are the most popular routes from Toronto to Chicago?
Most travelers choose Toronto Pearson Intl - Chicago O'Hare Intl, Hamilton - Chicago O'Hare Intl or Toronto Island - 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 EVA Air (95%), Egyptair (87%) and ANA (86%).
What are the cheapest flights from Toronto to Chicago?
Looking at all options, your cheapest flight can be booked for £75. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £138 on average, our data indicates £269 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, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of £63). Flying from Toronto to Chicago in February is currently the most expensive (average of £144). 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 27 November 2025.
Browse through other flights departing from Toronto. Flights are based on user searches made on Cheapflights and were last updated on 27 November 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 27 November 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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