This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28/11. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
20 Oct — 27 Oct1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in February or September, booked 88 days in advance, depart on a Friday or Saturday and return on a Thursday
Cheap flight deals from Toronto to Chicago
Enter your travel dates to find the best prices.
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Best
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Cheapest flights from Toronto to Chicago
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 20 September 2026.
Wed 4/1110:45 -
1 stop5h 07m
Wed 11/1113:55 -
Nonstop1h 47m
Deal found 20/9£155
Sat 21/1115:35 -
Nonstop2h 09m
Tue 24/1115:45 -
1 stop6h 11m
Deal found 18/9£158
Tue 3/1112:05 -
Nonstop2h 15m
Thu 5/1107:05 -
1 stop6h 16m
Deal found 19/9£158
Sat 24/1008:50 -
Nonstop1h 58m
Mon 26/1016:40 -
1 stop5h 46m
Deal found 17/9£159
Sun 4/1008:50 -
Nonstop1h 58m
Wed 7/1005:00 -
1 stop5h 43m
Deal found 16/9£160
Wed 7/1012:25 -
Nonstop1h 58m
Wed 14/1014:15 -
Nonstop1h 46m
Deal found 18/9£161
Wed 7/1014:00 -
Nonstop1h 55m
Tue 13/1020:40 -
Nonstop1h 46m
Deal found 18/9£162
Sat 10/1019:00 -
1 stop5h 21m
Thu 15/1009:55 -
Nonstop1h 45m
Deal found 19/9£163
Sat 3/1019:00 -
1 stop5h 21m
Mon 5/1014:52 -
Nonstop2h 04m
Deal found 18/9£163
Wed 7/1019:00 -
1 stop5h 21m
Fri 9/1020:40 -
Nonstop1h 46m
Deal found 16/9£164
Tue 20/1019:00 -
1 stop5h 21m
Wed 21/1011:05 -
1 stop6h 48m
Deal found 20/9£165
Mon 2/1109:00 -
1 stop7h 00m
Mon 9/1108:45 -
Nonstop1h 42m
Deal found 19/9£166
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 20 September 2026.
Sat 3/1007:00 -
Nonstop2h 00m
Tue 6/1012:59 -
Nonstop1h 47m
Deal found 19/9£172
Thu 15/1014:45 -
Nonstop2h 06m
Fri 16/1020:40 -
Nonstop1h 46m
Deal found 17/9£172
Wed 2/1216:35 -
Nonstop2h 05m
Sat 12/1212:20 -
Nonstop1h 46m
Deal found 20/9£179
Mon 2/1108:35 -
Nonstop2h 09m
Mon 9/1116:40 -
1 stop5h 46m
Deal found 18/9£172
Fri 23/1011:00 -
Nonstop2h 00m
Wed 28/1010:15 -
Nonstop1h 37m
Deal found 15/9£173
Wed 2/1216:35 -
Nonstop2h 05m
Sun 6/1212:20 -
Nonstop1h 46m
Deal found 20/9£179
Fri 2/1010:15 -
Nonstop2h 06m
Wed 7/1007:09 -
Nonstop1h 45m
Deal found 18/9£172
Sat 31/1017:55 -
Nonstop2h 10m
Sat 14/1107:05 -
1 stop6h 40m
Deal found 15/9£175
Wed 7/1007:00 -
Nonstop2h 00m
Wed 14/1014:37 -
1 stop8h 17m
Deal found 18/9£172
Wed 14/1021:00 -
Nonstop2h 06m
Wed 21/1005:00 -
1 stop7h 47m
Deal found 16/9£172
Thu 8/1007:00 -
Nonstop2h 00m
Sun 11/1017:53 -
Nonstop1h 51m
Deal found 20/9£173
Sun 11/1012:15 -
Nonstop2h 10m
Tue 13/1013:55 -
1 stop6h 35m
Deal found 18/9£219
Sun 29/1110:35 -
Nonstop2h 05m
Thu 10/1218:20 -
Nonstop1h 46m
Deal found 20/9£243
Fri 6/1117:55 -
Nonstop2h 10m
Mon 9/1114:21 -
1 stop8h 31m
Deal found 16/9£173
Sun 29/1110:35 -
Nonstop2h 05m
Fri 11/1212:20 -
Nonstop1h 46m
Deal found 20/9£243
Thu 1/1012:15 -
Nonstop2h 10m
Sun 4/1014:00 -
Nonstop1h 48m
Deal found 16/9£225
Fri 20/1109:44 -
1 stop6h 30m
Sun 22/1107:03 -
Nonstop1h 44m
Deal found 15/9£177
Fri 2/1012:15 -
Nonstop2h 10m
Mon 5/1013:55 -
1 stop6h 35m
Deal found 16/9£225
Thu 1/1014:30 -
1 stop10h 02m
Sun 4/1014:52 -
Nonstop2h 04m
Deal found 17/9£177
Sat 24/1012:15 -
Nonstop2h 10m
Wed 28/1007:05 -
2 stops10h 14m
Deal found 16/9£227
Tue 6/1012:15 -
Nonstop2h 10m
Fri 9/1013:55 -
1 stop6h 35m
Deal found 20/9£233
Sat 10/1012:15 -
Nonstop2h 10m
Fri 16/1012:55 -
1 stop5h 02m
Deal found 17/9£224
Thu 15/1012:15 -
Nonstop2h 10m
Thu 22/1012:55 -
1 stop5h 02m
Deal found 17/9£225
Sat 3/1012:15 -
Nonstop2h 10m
Sun 4/1014:00 -
Nonstop1h 48m
Deal found 19/9£225
Mon 2/1108:00 -
2 stops28h 07m
Mon 9/1106:10 -
1 stop9h 48m
Deal found 18/9£543
Tue 3/1116:05 -
3 stops27h 11m
Thu 5/1119:50 -
3 stops25h 20m
Deal found 19/9£679
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 20 September 2026.
Wed 7/1012:25 -
Nonstop1h 58m
Wed 14/1014:15 -
Nonstop1h 46m
Deal found 18/9£161
Wed 7/1014:00 -
Nonstop1h 55m
Tue 13/1020:40 -
Nonstop1h 46m
Deal found 18/9£162
Wed 7/1012:15 -
Nonstop2h 10m
Wed 14/1014:00 -
Nonstop1h 48m
Deal found 18/9£171
Thu 15/1021:00 -
Nonstop2h 06m
Sun 18/1014:52 -
Nonstop2h 04m
Deal found 17/9£172
Thu 8/1008:50 -
Nonstop1h 58m
Sat 17/1007:09 -
Nonstop1h 45m
Deal found 16/9£173
Thu 1/1011:00 -
Nonstop2h 00m
Sun 4/1009:55 -
Nonstop1h 45m
Deal found 16/9£174
Sat 24/1008:50 -
Nonstop1h 58m
Fri 30/1015:47 -
Nonstop1h 58m
Deal found 16/9£175
Wed 2/1216:35 -
Nonstop2h 05m
Tue 8/1218:20 -
Nonstop1h 46m
Deal found 20/9£179
Fri 27/1108:35 -
Nonstop2h 09m
Fri 8/107:01 -
Nonstop1h 46m
Deal found 16/9£198
Sat 17/1008:50 -
Nonstop1h 58m
Mon 19/1020:40 -
Nonstop1h 46m
Deal found 19/9£199
Mon 19/1008:50 -
Nonstop1h 58m
Mon 19/1016:33 -
Nonstop2h 04m
Deal found 17/9£201
Sun 11/1007:00 -
Nonstop2h 00m
Mon 12/1007:09 -
Nonstop1h 45m
Deal found 15/9£203
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 20 September 2026 and is based on user searches.
Fri 2/1019:43 -
1 stop4h 49m
Mon 5/1021:52 -
1 stop11h 12m
Deal found 18/9£170
Sat 3/1019:00 -
1 stop5h 21m
Mon 5/1014:52 -
Nonstop2h 04m
Deal found 18/9£163
Sun 4/1008:50 -
Nonstop1h 58m
Wed 7/1005:00 -
1 stop5h 43m
Deal found 16/9£160
Mon 5/1021:00 -
Nonstop2h 06m
Sat 17/1015:40 -
1 stop5h 13m
Deal found 20/9£158
Wed 7/1012:25 -
Nonstop1h 58m
Wed 14/1014:15 -
Nonstop1h 46m
Deal found 18/9£161
Wed 7/1014:00 -
Nonstop1h 55m
Tue 13/1020:40 -
Nonstop1h 46m
Deal found 18/9£162
Wed 7/1019:00 -
1 stop5h 21m
Fri 9/1020:40 -
Nonstop1h 46m
Deal found 16/9£164
Wed 7/1012:15 -
Nonstop2h 10m
Wed 14/1014:00 -
Nonstop1h 48m
Deal found 18/9£171
Sat 10/1019:00 -
1 stop5h 21m
Thu 15/1009:55 -
Nonstop1h 45m
Deal found 19/9£163
Tue 20/1019:00 -
1 stop5h 21m
Wed 21/1011:05 -
1 stop6h 48m
Deal found 20/9£165
Sat 24/1008:50 -
Nonstop1h 58m
Mon 26/1016:40 -
1 stop5h 46m
Deal found 17/9£159
Fri 30/1019:44 -
1 stop12h 46m
Wed 11/1107:05 -
1 stop6h 40m
Deal found 18/9£169
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 20 September 2026.
Sat 3/1008:50 -
Nonstop1h 58m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£106
Sun 11/1010:15 -
Nonstop2h 06m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 15/9£107
Thu 15/1012:45 -
1 stop5h 20m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 16/9£107
Mon 5/1019:00 -
1 stop15h 00m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£110
Sat 31/1016:35 -
Nonstop2h 05m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 16/9£113
Tue 6/1012:15 -
Nonstop2h 10m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 19/9£126
Wed 4/1112:05 -
Nonstop2h 15m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£127
Fri 16/1014:05 -
1 stop5h 41m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 18/9£128
Sun 15/1107:20 -
1 stop8h 07m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 16/9£131
Sat 17/1016:05 -
2 stops7h 24m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£132
Fri 9/1012:10 -
1 stop7h 19m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 15/9£134
Wed 21/1012:15 -
Nonstop2h 10m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 19/9£135
Find 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 20 September 2026.
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 7,457,451 searches. Data last updated 20 September 2026.
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
Cheapest return flight
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 28/11
06:45-07:54
Nonstop2h 09m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£106
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Wed 21/10
21:00-22:06
Nonstop2h 06m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£106
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 8/10
06:00-12:59
1 stop7h 59m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£110
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 10/10
19:00-09:00
1 stop15h 00m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£110
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Mon 9/11
09:44-16:21
1 stop7h 37m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£110
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Tue 6/10
12:15-13:25
Nonstop2h 10m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£126
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Wed 4/11
12:05-13:20
Nonstop2h 15m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£127
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 17/10
16:05-22:29
2 stops7h 24m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£132
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Wed 21/10
12:15-13:25
Nonstop2h 10m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£135
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Sat 24/10
15:15-23:31
1 stop9h 16m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£140
Flights are sorted by cheapest return flights first.
Deals found on 17/9
Showing 1-10 of 50 resultsSorted by cheapest first
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5
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.
YTO-CHI
YYZ-ORD
YTZ-ORD
YHM-ORD
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
YTO-CHI
YYZ-ORD
YTZ-ORD
YHM-ORD
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 £185). Flying from Toronto to Chicago in October is currently the most expensive (average of £244). 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 20 September 2026.
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 evening, which can drop the price by up to 20% versus a flight in the morning.
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 20 September 2026.
The most flights from YTO to CHI are scheduled on a Saturday (71 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (40 on average).
How much does it cost for a return flight from Toronto to Chicago?
Airfare is below average for this route at the moment.
Toronto to Chicago flights typically cost between £172 and £287 in November.The cheapest return price found within the last 5 days was £155 on Air Canada (4 Nov–11 Nov).
How often are flights from Toronto to Chicago delayed?
About 14% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 135 minutes.
What is the most punctual flight time for Toronto to Chicago flights?
Historically, flights departing in the morning 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?
Thursday 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, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.
How far ahead should I book a flight from Toronto to Chicago?
Booking 87 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.
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. United Airlines provides one of the quickest options available for as low as £172. Airlines will cover a distance of 436 mi. All flights are typically direct.
What are the most popular routes from Toronto to Chicago?
Most travelers choose Toronto Island - Chicago O'Hare Intl, Toronto Pearson Intl - 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 Sun Country Air (100%), Copa Airlines (84%) and Egyptair (81%).
What are the cheapest flights from Toronto to Chicago?
Looking at all options, your cheapest flight can be booked for £128. While the most popular route (Toronto Island - Chicago O'Hare Intl) can be booked for £171 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 £185). Flying from Toronto to Chicago in October is currently the most expensive (average of £244). 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 20 September 2026.
Browse through other flights departing from Toronto. Flights are based on user searches made on Cheapflights and were last updated on 20 September 2026.
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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