$87+ Cheap flights from Chicago (CHI) to Canada
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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Canada 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
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Cheapest flights from Chicago to CanadaExplore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
Explore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
This Flightnetwork 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 Flightnetwork 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 9/15![Porter Airlines logo]()
$213
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:20 pm -
Nonstop1h 46m
Sun 11/1510:35 am -
Nonstop2h 05m
Deal found 9/15![Porter Airlines logo]()
$213
This Kiwi.com 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 Kiwi.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 9/15![Porter Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 12/66:20 pm -
Nonstop1h 46m
Wed 12/1610:35 am -
Nonstop2h 05m
Deal found 9/13![Porter Airlines logo]()
$214
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:55 am -
Nonstop1h 45m
Sun 10/258:20 am -
Nonstop2h 03m
Deal found 9/15![Air Canada logo]()
$214
This Trip.com deal was found by Cheapflights users on 9/13. 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 10/2812:20 pm -
Nonstop1h 46m
Sun 11/110:35 am -
Nonstop2h 05m
Deal found 9/13![Porter Airlines logo]()
$215
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:20 pm -
Nonstop1h 40m
Tue 10/201:45 pm -
Nonstop1h 50m
Deal found 9/15![Porter Airlines logo]()
$216
This FlightHub deal was found by Cheapflights users on 9/14. 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 11/2012:20 pm -
Nonstop1h 46m
Sat 11/284:35 pm -
Nonstop2h 05m
Deal found 9/14![Porter Airlines logo]()
$216
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:55 am -
Nonstop1h 45m
Sun 10/1112:25 pm -
Nonstop1h 58m
Deal found 9/15![Air Canada logo]()
$216
This Trip.com 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 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
Mon 10/51:45 pm -
Nonstop1h 50m
Deal found 9/15![Porter Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 12/1012:20 pm -
Nonstop1h 46m
Sun 12/1310:35 am -
Nonstop2h 05m
Deal found 9/13![Porter Airlines logo]()
$217
This Kissandfly.com deal was found by Cheapflights users on 9/12. 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 10/19:55 am -
Nonstop1h 45m
Sun 10/48:05 am -
Nonstop1h 55m
Deal found 9/12![Air Canada logo]()
$217
Best flights from Chicago to CanadaDiscover carefully curated flight deals from Chicago to Canada that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Chicago to Canada that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
This Kiwi.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 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 9/16![Porter Airlines logo]()
$214
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.
Thu 10/296:17 pm -
Nonstop1h 58m
Sun 11/110:53 am -
Nonstop2h 04m
Deal found 9/15![United Airlines logo]()
$243
This United deal was found by Cheapflights users on 9/12. 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 10/1310:43 am -
Nonstop1h 59m
Thu 10/154:00 pm -
1 stop5h 12m
Deal found 9/12![Multiple Airlines logo]()
$252
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 10/29:29 am -
1 stop6h 51m
Sun 10/46:00 am -
1 stop7h 39m
Deal found 9/15![Delta logo]()
$269
This KAYAK deal was found by Cheapflights users on 9/13. 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.
Wed 9/307:25 am -
Nonstop1h 42m
Fri 10/27:35 pm -
Nonstop2h 10m
Deal found 9/13![Air Canada logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/146:00 am -
1 stop9h 35m
Sat 2/207:00 am -
1 stop5h 12m
Deal found 9/14![Alaska Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/211:45 am -
Nonstop1h 40m
Mon 10/51:45 pm -
Nonstop1h 50m
Deal found 9/12![Porter Airlines logo]()
$214
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:20 pm -
Nonstop1h 40m
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/15![Porter Airlines logo]()
$217
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 10/912:59 pm -
Nonstop1h 47m
Mon 10/1211:00 am -
Nonstop2h 00m
Deal found 9/15![United Airlines logo]()
$243
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.
Wed 10/219:52 pm -
1 stop11h 12m
Mon 10/264:30 pm -
Nonstop2h 13m
Deal found 9/15![Multiple Airlines logo]()
$253
This Trip.com 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 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
Mon 10/51:45 pm -
Nonstop1h 50m
Deal found 9/15![Porter Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 9/14. 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
Sun 10/187:00 am -
Nonstop2h 00m
Deal found 9/14![United Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 9/12. 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 11/159:30 am -
1 stop3h 00m
Wed 11/186:00 am -
1 stop4h 42m
Deal found 9/12![Delta logo]()
$269
This FlightHub deal was found by Cheapflights users on 9/13. 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 10/1111:45 am -
Nonstop1h 40m
Sun 10/1810:10 am -
Nonstop1h 50m
Deal found 9/13![Porter Airlines logo]()
$218
This United Airlines deal was found by Cheapflights users on 9/13. 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 9/282:52 pm -
Nonstop2h 04m
Sun 10/411:00 am -
Nonstop2h 00m
Deal found 9/13![United Airlines logo]()
$243
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.
Thu 10/19:29 am -
1 stop6h 51m
Sat 10/1012:10 pm -
1 stop6h 50m
Deal found 9/16![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Tue 10/132:52 pm -
Nonstop2h 04m
Thu 10/158:50 am -
Nonstop1h 58m
Deal found 9/12![United Airlines logo]()
$243
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:20 pm -
Nonstop1h 40m
Wed 10/1410:10 am -
Nonstop1h 50m
Deal found 9/15![Porter Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 9/13. 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
Sat 10/246:00 am -
1 stop7h 47m
Deal found 9/13![Delta logo]()
$269
This United deal was found by Cheapflights users on 9/14. 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 10/117:00 am -
1 stop15h 48m
Fri 10/1612:50 am -
1 stop7h 10m
Deal found 9/14![Multiple Airlines logo]()
$301
This KAYAK deal was found by Cheapflights users on 9/14. 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 10/68:45 am -
2 stops8h 35m
Thu 10/88:20 am -
1 stop4h 40m
Deal found 9/14![Air Canada logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 10/19:20 pm -
Nonstop1h 39m
Sat 10/38:50 am -
Nonstop1h 58m
Deal found 9/13![United Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 9/12. 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 10/19:29 am -
1 stop6h 51m
Sun 10/412:08 pm -
1 stop7h 25m
Deal found 9/12![Delta logo]()
$269
This FlightHub deal was found by Cheapflights users on 9/13. 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 10/93:20 pm -
Nonstop1h 40m
Mon 10/121:45 pm -
Nonstop1h 50m
Deal found 9/13![Porter Airlines logo]()
$231
This Air Canada deal was found by Cheapflights users on 9/11. 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.
Sat 10/32:00 pm -
Nonstop1h 48m
Sun 10/412:15 pm -
Nonstop2h 10m
Deal found 9/11![Air Canada logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/14. 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 11/67:03 am -
Nonstop1h 44m
Mon 11/97:26 pm -
Nonstop2h 22m
Deal found 9/14![United Airlines logo]()
$243
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.
Wed 11/259:30 am -
1 stop6h 50m
Mon 11/3012:15 pm -
1 stop6h 49m
Deal found 9/15![Delta logo]()
$269
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 10/238:40 am -
Nonstop3h 48m
Mon 10/266:00 am -
1 stop8h 38m
Deal found 9/15![Multiple Airlines logo]()
$338
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.
Thu 10/111:45 am -
Nonstop1h 40m
Sat 10/1010:10 am -
Nonstop1h 50m
Deal found 9/16![Porter Airlines logo]()
$232
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/66:00 am -
1 stop9h 35m
Wed 3/102:35 pm -
1 stop7h 24m
Deal found 9/14![Alaska Airlines logo]()
$428
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated September 16, 2026 and is based on user searches.
This Flightnetwork 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 Flightnetwork 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 9/15![Porter Airlines logo]()
$213
This Trip.com 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 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
Mon 10/51:45 pm -
Nonstop1h 50m
Deal found 9/15![Porter Airlines logo]()
$217
This Kissandfly.com deal was found by Cheapflights users on 9/13. 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 10/19:55 am -
Nonstop1h 45m
Sun 10/48:05 am -
Nonstop1h 55m
Deal found 9/13![Air Canada logo]()
$217
This Kiwi.com 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 Kiwi.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 9/15![Porter Airlines logo]()
$214
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:55 am -
Nonstop1h 45m
Sun 10/1112:25 pm -
Nonstop1h 58m
Deal found 9/15![Air Canada logo]()
$216
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:20 pm -
Nonstop1h 40m
Tue 10/201:45 pm -
Nonstop1h 50m
Deal found 9/15![Porter Airlines logo]()
$216
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:55 am -
Nonstop1h 45m
Sun 10/258:20 am -
Nonstop2h 03m
Deal found 9/15![Air Canada logo]()
$214
This Booking.com deal was found by Cheapflights users on 9/13. 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 10/222:00 pm -
Nonstop1h 48m
Sun 10/254:35 pm -
Nonstop2h 05m
Deal found 9/13![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/276:20 pm -
Nonstop1h 46m
Thu 10/2910:35 am -
Nonstop2h 05m
Deal found 9/11![Porter Airlines logo]()
$214
This Trip.com deal was found by Cheapflights users on 9/12. 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
Tue 11/34:35 pm -
Nonstop2h 05m
Deal found 9/12![Porter Airlines logo]()
$216
This Trip.com deal was found by Cheapflights users on 9/13. 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 10/2812:20 pm -
Nonstop1h 46m
Sun 11/110:35 am -
Nonstop2h 05m
Deal found 9/13![Porter Airlines logo]()
$215
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:20 pm -
Nonstop1h 46m
Sun 11/14:35 pm -
Nonstop2h 05m
Deal found 9/15![Porter Airlines logo]()
$213
One-way flights from Chicago to CanadaSearch for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This FlightHub deal was found by Cheapflights users on 9/13. 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 11/112:20 pm -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Porter Airlines logo]()
$87
This Air Canada deal was found by Cheapflights users on 9/12. 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 10/29:55 am -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Air Canada logo]()
$95
This Mytrip deal was found by Cheapflights users on 9/14. 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 10/2612:20 pm -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Porter Airlines logo]()
$96
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:05 am -
1 stop6h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$96
This Mytrip deal was found by Cheapflights users on 9/14. 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 10/2411:45 am -
Nonstop1h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Porter Airlines logo]()
$97
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Thu 10/222:00 pm -
Nonstop1h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Air Canada logo]()
$97
This Mytrip deal was found by Cheapflights users on 9/12. 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 9/272:00 pm -
Nonstop1h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Air Canada logo]()
$98
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:05 am -
1 stop6h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$98
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:45 pm -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$99
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Thu 10/223:20 pm -
Nonstop1h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Porter Airlines logo]()
$100
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:20 pm -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Porter Airlines logo]()
$100
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:45 am -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$101
Find flight deals from Chicago to Canada
Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Flightnetwork) |
One-way from | $87 (FlightHub) |
Popular in | August |
Cheapest in | March |
Average price | $298 |
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 Canada 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 16, 2026.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoToronto
ORD Chicago O'Hare Intl - YTZ Toronto Island
ORDYTZ
Chicago O'Hare Intl
Wed 10/14
8:45 am-6:20 pm
2 stops8h 35m
Toronto Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$97
Quickest round-trip
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Sat 10/24
11:45 am-2:25 pm
Nonstop1h 40m
Toronto Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Wed 10/7
6:00 am-11:43 am
1 stop4h 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
Thu 10/8
8:29 am-5:19 pm
1 stop7h 50m
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
Tue 10/13
9:35 pm-9:19 am
1 stop10h 44m
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 10/9
1:26 pm-10:56 pm
1 stop8h 30m
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 9/28
3:00 pm-10:23 pm
1 stop6h 23m
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 10/15
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 10/26
4:40 pm-11:26 pm
1 stop5h 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 12/10
8:39 am-5:20 pm
1 stop7h 41m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Canada
Have a flexible travel schedule? Discover the best time to fly to Canada from Chicago with our price prediction graph.
MDW-YTZ
ORD-YYZ
MDW-YYZ
ORD-YTZ
ORD-YVR
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 Canada
CHI-CA0
MDW-YTZ
ORD-YYZ
MDW-YYZ
ORD-YTZ
What is the cheapest month to book a flight from Chicago to Canada?
Currently, February is the cheapest month in which you can book a flight from Chicago to Canada (average of $333). Flying from Chicago to Canada in July is currently the most expensive (average of $441). 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 CA?
Find hourly flight availability from Chicago to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2026.
When flying from Chicago to Canada, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 5% versus a flight in the evening.
Weekly flight availability from Chicago to Canada
Explore weekly flight availability from Chicago to Canada. 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 16, 2026.
The most flights from CHI to CA0 are scheduled on a Monday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 on average).
How often are flights from Chicago to Canada delayed?
About 22% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 138 minutes.
What is the most punctual flight time for Chicago to Canada 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 Sunday 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 Canada flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.
How far ahead should I book a flight from Chicago to Canada?
Booking 47 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Canada. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to Canada?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Canada. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Tuesday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Canada
Get insights into the airlines that provide service to Canada. 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 Canada. Reviews last updated September 16, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet from Chicago to Canada 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
Entertainment
6.9
Overall
8.0
Comfort
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Related info for your journey
Find useful and relevant information for your journey from Chicago to Canada. 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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Alternative routes for Chicago to Canada
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Canada by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Canada by cabin class
Find flights from Chicago to Canada, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Canada flights
Browse other Chicago and Canada flight options. Last updated on September 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Canada flights
Consider these flights traveling from Chicago to Canada.
Fly to Canada regions
Consider these flights traveling to Canada regions.
Top 9 airlines flying from Chicago to Canada
Discover the top 9 airlines that operate flights from Chicago to Canada. 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 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$315 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$466 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$139 | Average$350 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$153 | Average$566 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$160 | Average$336 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$209 | Average$540 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$217 | Average$343 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$381 | Average$385 | FlexibilityNo cancel fee | On-time68% |