$95+ Cheap flights from Chicago (CHI) to Toronto (YTO)
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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTO
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Toronto 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 Chicago to Toronto are usually found in January or March, booked 47 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Chicago to Toronto
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Cheapest flights from Chicago to TorontoExplore the most affordable flight options available from Chicago to Toronto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
Explore the most affordable flight options available from Chicago to Toronto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
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.
Wed 10/2111:45 am -
Nonstop1h 40m
Fri 10/231:45 pm -
Nonstop1h 50m
Deal found 9/19![Porter Airlines logo]()
$213
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/21:55 pm -
Nonstop1h 47m
Mon 11/910:35 am -
Nonstop2h 05m
Deal found 9/18![Multiple Airlines logo]()
$213
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.
Sat 10/103:40 pm -
1 stop5h 13m
Mon 10/128:05 am -
Nonstop1h 55m
Deal found 9/18![Air Canada logo]()
$213
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.
Tue 10/2011:45 am -
Nonstop1h 40m
Sat 10/2410:10 am -
Nonstop1h 50m
Deal found 9/18![Porter Airlines logo]()
$214
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.
Sun 10/2512:20 pm -
Nonstop1h 46m
Mon 10/2610:35 am -
Nonstop2h 05m
Deal found 9/18![Porter Airlines logo]()
$214
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:40 pm -
Nonstop1h 46m
Sun 10/48:05 am -
Nonstop1h 55m
Deal found 9/17![Air Canada logo]()
$214
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
Nonstop1h 40m
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/17![Porter Airlines logo]()
$215
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:20 pm -
Nonstop1h 46m
Tue 11/1710:35 am -
Nonstop2h 05m
Deal found 9/20![Porter Airlines logo]()
$215
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.
Mon 10/192:15 pm -
Nonstop1h 46m
Tue 10/208:05 am -
Nonstop1h 55m
Deal found 9/16![Air Canada logo]()
$215
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.
Sat 10/311:45 am -
Nonstop1h 40m
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/18![Porter Airlines logo]()
$216
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:00 pm -
Nonstop1h 48m
Sun 10/1112:15 pm -
Nonstop2h 10m
Deal found 9/20![Air Canada logo]()
$216
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:50 pm -
Nonstop1h 43m
Tue 11/101:00 pm -
1 stop7h 52m
Deal found 9/19![Air Canada logo]()
$216
Best flights from Chicago to TorontoDiscover carefully curated flight deals from Chicago to Toronto that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Chicago to Toronto that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
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.
Mon 10/193:20 pm -
Nonstop1h 40m
Tue 10/201:45 pm -
Nonstop1h 50m
Deal found 9/16![Porter Airlines logo]()
$213
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:47 pm -
Nonstop1h 58m
Thu 11/1910:53 am -
Nonstop2h 04m
Deal found 9/20![United Airlines logo]()
$243
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:47 pm -
Nonstop1h 58m
Tue 11/39:00 am -
1 stop6h 52m
Deal found 9/16![Multiple Airlines logo]()
$252
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:29 am -
1 stop6h 51m
Sun 10/412:08 pm -
1 stop7h 25m
Deal found 9/16![Delta logo]()
$268
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:00 pm -
Nonstop1h 48m
Thu 10/226:50 am -
1 stop5h 31m
Deal found 9/16![Air Canada logo]()
$329
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:45 am -
Nonstop1h 40m
Sun 10/1810:10 am -
Nonstop1h 50m
Deal found 9/17![Porter Airlines logo]()
$216
This Trip.com deal was found by Cheapflights users on 9/21. 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.
Sat 10/103:20 pm -
Nonstop1h 40m
Mon 10/121:45 pm -
Nonstop1h 50m
Deal found 9/21![Porter Airlines logo]()
$217
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.
Mon 10/192:52 pm -
Nonstop2h 04m
Fri 10/231:00 pm -
Nonstop2h 05m
Deal found 9/18![United Airlines logo]()
$243
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:20 pm -
Nonstop1h 39m
Tue 10/134:00 pm -
1 stop5h 12m
Deal found 9/20![Multiple Airlines logo]()
$252
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 10/143:20 pm -
Nonstop1h 40m
Tue 10/201:45 pm -
Nonstop1h 50m
Deal found 9/16![Porter Airlines logo]()
$217
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.
Sun 10/257:03 am -
Nonstop1h 44m
Thu 10/296:45 am -
Nonstop2h 09m
Deal found 9/19![United Airlines logo]()
$243
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.
Fri 10/96:44 pm -
1 stop3h 12m
Sun 10/1112:10 pm -
1 stop6h 50m
Deal found 9/18![Delta logo]()
$268
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:53 pm -
Nonstop1h 51m
Sat 10/244:00 pm -
1 stop5h 12m
Deal found 9/20![Multiple Airlines logo]()
$252
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.
Thu 10/13:20 pm -
Nonstop1h 40m
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/17![Porter Airlines logo]()
$218
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.
Mon 11/233:47 pm -
Nonstop1h 58m
Tue 11/2410:53 am -
Nonstop2h 04m
Deal found 9/19![United Airlines logo]()
$243
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:29 am -
1 stop6h 50m
Sun 10/252:26 pm -
1 stop4h 34m
Deal found 9/20![Delta logo]()
$268
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:57 pm -
Nonstop1h 50m
Wed 11/118:35 am -
Nonstop2h 09m
Deal found 9/20![United Airlines logo]()
$243
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.
Fri 10/23:20 pm -
Nonstop1h 40m
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/18![Porter Airlines logo]()
$221
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:29 am -
1 stop6h 50m
Thu 11/196:00 am -
1 stop7h 51m
Deal found 9/20![Delta logo]()
$268
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.
Tue 10/131:27 pm -
1 stop8h 29m
Sat 10/1712:10 pm -
1 stop6h 50m
Deal found 9/18![Delta logo]()
$268
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.
Thu 10/153:20 pm -
Nonstop1h 40m
Sun 10/1810:10 am -
Nonstop1h 50m
Deal found 9/16![Porter Airlines logo]()
$222
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:09 am -
Nonstop1h 45m
Mon 10/128:50 am -
Nonstop1h 58m
Deal found 9/20![United Airlines logo]()
$247
This WestJet deal was found by Cheapflights users on 9/21. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:30 pm -
1 stop22h 45m
Sun 10/186:10 pm -
1 stop23h 30m
Deal found 9/21![WestJet logo]()
$766
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:29 am -
1 stop3h 07m
Sun 10/1812:10 pm -
1 stop6h 50m
Deal found 9/20![Delta logo]()
$268
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:20 pm -
Nonstop1h 40m
Sun 10/1110:10 am -
Nonstop1h 50m
Deal found 9/20![Porter Airlines logo]()
$226
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 11/142:30 pm -
1 stop7h 56m
Mon 11/166:45 am -
Nonstop2h 09m
Deal found 9/17![United Airlines logo]()
$253
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:44 pm -
1 stop3h 12m
Tue 10/2712:10 pm -
1 stop6h 50m
Deal found 9/20![Delta logo]()
$268
This Justfly.com deal was found by Cheapflights users on 9/21. 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.
Thu 10/83:20 pm -
Nonstop1h 40m
Mon 10/121:45 pm -
Nonstop1h 50m
Deal found 9/21![Porter Airlines logo]()
$230
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 10/167:09 am -
Nonstop1h 45m
Mon 10/197:00 pm -
1 stop5h 21m
Deal found 9/18![United Airlines logo]()
$258
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:44 pm -
1 stop3h 12m
Sat 11/146:00 am -
1 stop7h 51m
Deal found 9/20![Delta logo]()
$268
Last-minute flights from Chicago to TorontoDiscover last-minute flight deals from Chicago to Toronto. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Toronto. Data last updated September 21, 2026 and is based on user searches.
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
Nonstop1h 40m
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/17![Porter Airlines logo]()
$215
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:40 pm -
Nonstop1h 46m
Sun 10/48:05 am -
Nonstop1h 55m
Deal found 9/17![Air Canada logo]()
$214
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.
Sat 10/311:45 am -
Nonstop1h 40m
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/18![Porter Airlines logo]()
$216
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:45 am -
Nonstop1h 40m
Mon 10/510:10 am -
Nonstop1h 50m
Deal found 9/19![Porter Airlines logo]()
$217
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:00 pm -
Nonstop1h 48m
Sun 10/1112:15 pm -
Nonstop2h 10m
Deal found 9/20![Air Canada logo]()
$216
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.
Sat 10/103:40 pm -
1 stop5h 13m
Mon 10/128:05 am -
Nonstop1h 55m
Deal found 9/18![Air Canada logo]()
$213
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.
Mon 10/192:15 pm -
Nonstop1h 46m
Tue 10/208:05 am -
Nonstop1h 55m
Deal found 9/16![Air Canada logo]()
$215
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.
Tue 10/203:20 pm -
Nonstop1h 40m
Thu 10/2210:10 am -
Nonstop1h 50m
Deal found 9/18![Porter Airlines logo]()
$214
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.
Wed 10/2111:45 am -
Nonstop1h 40m
Fri 10/231:45 pm -
Nonstop1h 50m
Deal found 9/19![Porter Airlines logo]()
$213
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2512:20 pm -
Nonstop1h 46m
Thu 10/2910:35 am -
Nonstop2h 05m
Deal found 9/17![Porter Airlines logo]()
$213
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.
Sun 10/256:20 pm -
Nonstop1h 46m
Tue 10/2710:35 am -
Nonstop2h 05m
Deal found 9/18![Porter Airlines logo]()
$214
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.
Tue 10/2712:20 pm -
Nonstop1h 46m
Mon 11/210:35 am -
Nonstop2h 05m
Deal found 9/16![Porter Airlines logo]()
$217
One-way flights from Chicago to TorontoSearch for one-way flight options from Chicago to Toronto. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Chicago to Toronto. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:00 pm -
Nonstop1h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Air Canada logo]()
$95
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:46 am -
Nonstop1h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![American Airlines logo]()
$95
This Flybillet 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 Flybillet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:50 pm -
Nonstop1h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$99
This Flybillet 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 Flybillet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:55 am -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$100
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:05 am -
1 stop6h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Air Canada logo]()
$104
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.
Tue 10/208:45 am -
1 stop6h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$104
This Delta deal was found by Cheapflights users on 9/21. 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.
Sun 10/185:29 pm -
1 stop4h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$105
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:30 am -
1 stop3h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$105
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.
Sun 10/189:55 am -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$107
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.
Thu 10/1511:45 am -
Nonstop1h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Air Transat logo]()
$108
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.
Sun 10/182:00 pm -
Nonstop1h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$108
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.
Sun 10/184:33 pm -
Nonstop2h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$108
Find flight deals from Chicago to Toronto
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Toronto (YTO). 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 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Kiwi.com) |
One-way from | $95 (Air Canada) |
Popular in | September |
Cheapest in | January |
Average price | $316 |
Good round-trip deal | $205 or less |
Good one-way deal | $87 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Toronto 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 21, 2026.
Use the filters below to find and compare flights from Chicago to Toronto that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Tue 10/20
5:53 pm-8:44 pm
Nonstop1h 51m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$95
Quickest round-trip
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Wed 12/9
9:21 pm-11:59 pm
Nonstop1h 38m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$95
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Sun 10/18
5:29 pm-10:56 pm
1 stop4h 27m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Sat 11/21
5:05 pm-10:57 pm
1 stop4h 52m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Wed 10/7
5:00 am-11:43 am
1 stop5h 43m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Sun 11/1
5:29 pm-10:56 pm
1 stop4h 27m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Fri 10/30
3:40 pm-11:26 pm
1 stop6h 46m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Thu 10/22
1:55 pm-10:56 pm
1 stop8h 01m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Mon 11/9
5:55 am-2:25 pm
1 stop7h 30m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoToronto
MDW Chicago Midway - YYZ Toronto Pearson Intl
MDWYYZ
Chicago Midway
Thu 10/15
9:29 am-1:36 pm
1 stop3h 07m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Chicago to Toronto
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 Chicago to Toronto 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*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Chicago-Toronto flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Toronto flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Toronto flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Toronto 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 Chicago-Toronto 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 Chicago to Toronto
Have a flexible travel schedule? Discover the best time to fly to Toronto from Chicago with our price prediction graph.
CHI-YTO
MDW-YTZ
ORD-YYZ
MDW-YYZ
ORD-YTZ
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 Chicago to Toronto
CHI-YTO
MDW-YTZ
ORD-YYZ
MDW-YYZ
ORD-YTZ
What is the cheapest month to book a flight from Chicago to Toronto?
Currently, February is the cheapest month in which you can book a flight from Chicago to Toronto (average of $286). Flying from Chicago to Toronto in August is currently the most expensive (average of $358). 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 CHI to YTO?
Find hourly flight availability from Chicago to Toronto. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 21, 2026.
It’s optimal to fly from Chicago to Toronto in the morning. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Chicago to Toronto
Explore weekly flight availability from Chicago to Toronto. 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 21, 2026.
The most flights from CHI to YTO 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 (43 on average).
How much does it cost to fly round-trip from Chicago to Toronto?
Airfare is below average for this route at the moment.
Chicago to Toronto flights typically cost between $234 and $406 in October.The cheapest round-trip price found within the last 5 days was $213 on Porter Airlines (Oct 21-Oct 23).
How often are flights from Chicago to Toronto delayed?
About 21% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 132 minutes.
What is the most punctual flight time for Chicago to Toronto 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?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Toronto flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
How far ahead should I book a flight from Chicago to Toronto?
The price you pay for your flight from Chicago to Toronto may vary depending on when you book. For the best chance of a lower fare, look to book 71 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago to Toronto?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Toronto. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Chicago to Toronto flight should consider departing on Saturday mornings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to Toronto 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 Chicago to Toronto trip
Our travel experts
Reviews of airlines servicing Toronto
Get insights into the airlines that provide service to Toronto. 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 Toronto. Reviews last updated September 21, 2026.
Read reviews from past customers who have flown Porter Airlines,Delta, andUnited Airlines from Chicago to Toronto. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.2
Overall
8.0
Comfort
8.0
Food
7.6
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Boarding
8.2
Overall
8.0
Comfort
8.0
Food
7.6
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Boarding
8.2
Overall
8.0
Comfort
8.0
Food
7.6
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Boarding
8.2
Overall
8.0
Comfort
8.0
Food
7.6
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Boarding
8.2
Overall
8.0
Comfort
8.0
Food
7.6
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Boarding
8.2
Overall
8.0
Comfort
8.0
Food
7.6
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Related info for your journey
Find useful and relevant information for your journey from Chicago to Toronto. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip
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Search flights from Chicago to Toronto by cabin class
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Chicago and Toronto flights
Browse other Chicago and Toronto flight options. Last updated on September 21, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Toronto
Explore flights to Toronto departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Top 6 airlines flying from Chicago to Toronto
Discover the top 6 airlines that operate flights from Chicago to Toronto. 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$387 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$170 | Average$291 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$193 | Average$348 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$222 | Average$353 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$223 | Average$379 | FlexibilityNo cancel fee | On-time71% |