$129+ Cheap flights from Toronto (YTO) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Oct 20 — Oct 271
Round-trip
1 adult, Economy
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Find cheap flights from Toronto 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.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 Thursday and return on a Thursday
Cheap flight deals from Toronto to Chicago
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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 September 20, 2026.
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 September 20, 2026.
This Kissandfly.com deal was found by Cheapflights users on 9/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
Nonstop2h 00m
Sun 10/119:55 am -
Nonstop1h 45m
Deal found 9/20![Air Canada logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Sun 10/1110:10 am -
Nonstop1h 50m
Fri 10/1611:45 am -
Nonstop1h 40m
Deal found 9/19![Porter Airlines logo]()
$206
This Kissandfly.com deal was found by Cheapflights users on 9/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:15 pm -
Nonstop2h 10m
Sun 10/42:00 pm -
Nonstop1h 48m
Deal found 9/19![Air Canada logo]()
$206
This Trip.com deal was found by Cheapflights users on 9/18. 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.
Fri 10/21:45 pm -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$207
This Flightnetwork deal was found by Cheapflights users on 9/18. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:20 am -
2 stops7h 40m
Mon 11/91:55 pm -
Nonstop1h 47m
Deal found 9/18![Air Canada logo]()
$207
This Booking.com deal was found by Cheapflights users on 9/18. 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.
Fri 10/24:00 pm -
1 stop5h 12m
Sun 10/48:40 pm -
Nonstop1h 46m
Deal found 9/18![Air Canada logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Thu 12/34:35 pm -
Nonstop2h 05m
Tue 12/812:20 pm -
Nonstop1h 46m
Deal found 9/19![Porter Airlines logo]()
$208
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:15 pm -
Nonstop2h 10m
Sun 10/42:00 pm -
Nonstop1h 48m
Deal found 9/16![Air Canada logo]()
$209
This Kissandfly.com deal was found by Cheapflights users on 9/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:00 am -
Nonstop2h 00m
Sun 10/118:50 am -
Nonstop1h 59m
Deal found 9/20![Lufthansa logo]()
$210
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:45 pm -
Nonstop1h 50m
Sun 10/1111:45 am -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$210
This Justfly.com deal was found by Cheapflights users on 9/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:45 pm -
Nonstop1h 50m
Wed 10/711:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$211
This Air Canada deal was found by Cheapflights users on 9/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:00 pm -
1 stop5h 12m
Sun 10/2510:15 am -
Nonstop1h 37m
Deal found 9/16![Air Canada logo]()
$212
Best flights from Toronto to ChicagoDiscover carefully curated flight deals from Toronto to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
Discover carefully curated flight deals from Toronto to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
This iWofly deal was found by Cheapflights users on 9/16. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:30 am -
1 stop6h 22m
Sun 10/42:00 pm -
Nonstop1h 48m
Deal found 9/16![Air Canada logo]()
$219
This SmartFares deal was found by Cheapflights users on 9/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:45 pm -
Nonstop1h 50m
Tue 10/133:20 pm -
Nonstop1h 40m
Deal found 9/19![Air Transat logo]()
$227
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:00 pm -
Nonstop2h 06m
Wed 10/215:00 am -
1 stop7h 47m
Deal found 9/16![United Airlines logo]()
$231
This United deal was found by Cheapflights users on 9/17. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:45 pm -
Nonstop2h 06m
Fri 10/168:40 pm -
Nonstop1h 46m
Deal found 9/17![Multiple Airlines logo]()
$231
This FlightHub deal was found by Cheapflights users on 9/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/111:45 pm -
Nonstop1h 50m
Thu 10/153:20 pm -
Nonstop1h 40m
Deal found 9/19![Porter Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:45 am -
1 stop4h 06m
Thu 11/191:31 pm -
1 stop8h 26m
Deal found 9/18![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
1 stop6h 13m
Sun 10/47:09 am -
Nonstop1h 45m
Deal found 9/19![United Airlines logo]()
$231
This United deal was found by Cheapflights users on 9/15. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:55 pm -
Nonstop2h 10m
Sat 11/147:05 am -
1 stop6h 40m
Deal found 9/15![Multiple Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:05 pm -
1 stop3h 17m
Tue 10/69:29 am -
1 stop6h 50m
Deal found 9/17![Delta logo]()
$237
This Porter Airlines deal was found by Cheapflights users on 9/19. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:45 pm -
Nonstop1h 50m
Fri 10/2311:45 am -
Nonstop1h 40m
Deal found 9/19![Porter Airlines logo]()
$240
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:35 pm -
Nonstop2h 09m
Thu 12/101:57 pm -
Nonstop1h 50m
Deal found 9/19![United Airlines logo]()
$231
This United deal was found by Cheapflights users on 9/19. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:30 am -
1 stop5h 44m
Thu 11/128:40 pm -
Nonstop1h 43m
Deal found 9/19![Multiple Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop7h 51m
Sun 11/229:30 am -
1 stop6h 50m
Deal found 9/17![Delta logo]()
$237
This Porter Airlines deal was found by Cheapflights users on 9/17. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:10 am -
Nonstop1h 50m
Fri 10/93:20 pm -
Nonstop1h 40m
Deal found 9/17![Porter Airlines logo]()
$241
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:50 am -
Nonstop1h 58m
Sun 10/49:20 pm -
Nonstop1h 39m
Deal found 9/18![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 9/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:00 am -
1 stop4h 32m
Sat 11/71:27 pm -
1 stop8h 29m
Deal found 9/19![Delta logo]()
$237
This Trip.com deal was found by Cheapflights users on 9/18. 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.
Fri 10/210:10 am -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Multiple Airlines logo]()
$240
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/131:45 pm -
Nonstop1h 50m
Tue 10/2011:45 am -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$254
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:50 am -
Nonstop1h 58m
Mon 10/264:40 pm -
1 stop5h 46m
Deal found 9/17![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:00 am -
1 stop7h 47m
Wed 10/281:27 pm -
1 stop8h 29m
Deal found 9/15![Delta logo]()
$238
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:15 am -
Nonstop2h 06m
Wed 10/77:09 am -
Nonstop1h 45m
Deal found 9/18![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop4h 32m
Sat 10/246:44 pm -
1 stop3h 12m
Deal found 9/15![Delta logo]()
$238
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:55 pm -
Nonstop2h 10m
Mon 11/92:21 pm -
1 stop8h 31m
Deal found 9/16![United Airlines logo]()
$232
This FlightHub deal was found by Cheapflights users on 9/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:45 pm -
Nonstop1h 50m
Sun 10/1111:45 am -
Nonstop1h 40m
Deal found 9/15![Porter Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:00 am -
1 stop7h 47m
Tue 11/36:44 pm -
1 stop3h 12m
Deal found 9/15![Delta logo]()
$238
This United deal was found by Cheapflights users on 9/18. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1112:15 pm -
Nonstop2h 10m
Tue 10/131:55 pm -
1 stop6h 35m
Deal found 9/18![Multiple Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:44 am -
1 stop6h 30m
Sun 11/227:03 am -
Nonstop1h 44m
Deal found 9/15![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:00 am -
1 stop7h 51m
Sun 11/229:30 am -
1 stop6h 50m
Deal found 9/15![Delta logo]()
$238
This United deal was found by Cheapflights users on 9/15. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:15 pm -
Nonstop2h 10m
Sat 10/1710:50 am -
1 stop6h 30m
Deal found 9/15![Multiple Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:30 pm -
1 stop10h 02m
Tue 10/1312:55 pm -
1 stop9h 59m
Deal found 9/19![United Airlines logo]()
$237
Last-minute flights from Toronto to ChicagoDiscover last-minute flight deals from Toronto to Chicago. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Toronto to Chicago. Data last updated September 20, 2026 and is based on user searches.
This Kissandfly.com deal was found by Cheapflights users on 9/17. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:15 pm -
Nonstop2h 10m
Sun 10/42:00 pm -
Nonstop1h 48m
Deal found 9/17![Air Canada logo]()
$208
This Trip.com deal was found by Cheapflights users on 9/18. 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.
Fri 10/21:45 pm -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$207
This Booking.com deal was found by Cheapflights users on 9/18. 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.
Fri 10/24:00 pm -
1 stop5h 12m
Sun 10/48:40 pm -
Nonstop1h 46m
Deal found 9/18![Air Canada logo]()
$208
This Porter Airlines deal was found by Cheapflights users on 9/18. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sat 10/311:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$212
This Air Canada deal was found by Cheapflights users on 9/18. 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.
Fri 10/212:15 pm -
Nonstop2h 10m
Tue 10/62:00 pm -
Nonstop1h 48m
Deal found 9/18![Air Canada logo]()
$212
This Kissandfly.com deal was found by Cheapflights users on 9/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:15 pm -
Nonstop2h 10m
Sun 10/42:00 pm -
Nonstop1h 48m
Deal found 9/19![Air Canada logo]()
$206
This Justfly.com deal was found by Cheapflights users on 9/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:45 pm -
Nonstop1h 50m
Wed 10/711:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$211
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:45 pm -
Nonstop1h 50m
Sun 10/1111:45 am -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$210
This Kissandfly.com deal was found by Cheapflights users on 9/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
Nonstop2h 00m
Sun 10/119:55 am -
Nonstop1h 45m
Deal found 9/20![Air Canada logo]()
$206
This Kissandfly.com deal was found by Cheapflights users on 9/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:00 am -
Nonstop2h 00m
Sun 10/118:50 am -
Nonstop1h 59m
Deal found 9/20![Lufthansa logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Sun 10/1110:10 am -
Nonstop1h 50m
Fri 10/1611:45 am -
Nonstop1h 40m
Deal found 9/19![Porter Airlines logo]()
$206
This Air Canada deal was found by Cheapflights users on 9/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:00 pm -
1 stop5h 12m
Sun 10/2510:15 am -
Nonstop1h 37m
Deal found 9/16![Air Canada logo]()
$212
One-way flights from Toronto to ChicagoSearch for one-way flight options from Toronto to Chicago. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
Search for one-way flight options from Toronto to Chicago. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Mytrip deal was found by Cheapflights users on 9/19. 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.
Tue 11/34:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Porter Airlines logo]()
$129
This Kissandfly.com deal was found by Cheapflights users on 9/16. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/304:00 pm -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$130
This Mytrip deal was found by Cheapflights users on 9/19. 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.
Sat 10/310:10 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Porter Airlines logo]()
$130
This Justfly.com deal was found by Cheapflights users on 9/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Porter Airlines logo]()
$130
This Flysmarter deal was found by Cheapflights users on 9/16. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:00 pm -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$131
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:10 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Porter Airlines logo]()
$131
This FlightHub deal was found by Cheapflights users on 9/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:35 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Porter Airlines logo]()
$131
This Trip.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/231:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Porter Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Thu 10/294:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Porter Airlines logo]()
$132
This Mytrip deal was found by Cheapflights users on 9/20. 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.
Sun 10/258:20 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Air Canada logo]()
$133
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Porter Airlines logo]()
$133
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Porter Airlines logo]()
$133
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 September 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Kissandfly.com) |
One-way from | $129 (Mytrip) |
Popular in | October |
Cheapest in | February |
Average price | $252 |
Good round-trip deal | $230 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize 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 September 20, 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
Cheapest round-trip
Quickest round-trip
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sun 10/11
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Mon 10/5
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 9/29
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Fri 10/16
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Sun 10/11
8:20 am-12:00 pm
1 stop4h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Fri 10/2
11:00 am-12:00 pm
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 10/3
1:00 pm-2:05 pm
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Wed 10/14
11:00 am-12:00 pm
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Wed 10/21
9:00 pm-10:06 pm
Nonstop2h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 10/17
7:00 pm-11:21 pm
1 stop5h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Toronto 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 to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Toronto-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Toronto-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-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 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-MDW
YTZ-ORD
YYZ-MDW
Estimated round-trip 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-MDW
YTZ-ORD
YYZ-MDW
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 $248). Flying from Toronto to Chicago in October is currently the most expensive (average of $327). 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 September 20, 2026.
A simple way to save on the total cost of your ticket is to fly from Toronto to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the afternoon.
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 September 20, 2026.
The most flights from YTO to CHI are scheduled on a Friday (78 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 to fly round-trip from Toronto to Chicago?
Airfare is below average for this route at the moment.
Toronto to Chicago flights typically cost between $231 and $384 in October.The cheapest round-trip price found within the last 5 days was $206 on Air Canada (Oct 8-Oct 11).
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 last 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?
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 87 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Toronto to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Toronto to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Toronto to Chicago trip
Our travel experts
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 September 20, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,United Airlines, andAir Canada from Toronto to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.2
Comfort
8.0
Food
7.6
Entertainment
6.9
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Comfort
8.0
Food
7.6
Entertainment
6.9
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Comfort
8.0
Food
7.6
Entertainment
6.9
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Comfort
8.0
Food
7.6
Entertainment
6.9
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Comfort
8.0
Food
7.6
Entertainment
6.9
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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.
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 20, 2026.
Complete your trip
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Toronto and Chicago flights
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Other flights from Toronto
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Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Toronto to Chicago
Discover the top 4 airlines 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 7,457,451 searches. Data last updated September 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$287 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$185 | Average$384 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$190 | Average$286 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$193 | Average$319 | FlexibilityNo cancel fee | On-time71% |