$104+ Cheap flights from Chicago (CHI) to Canada
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Sep 16 — Sep 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Canada
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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 August 17, 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 August 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:20 pm -
Nonstop1h 40m
Thu 9/1710:10 am -
Nonstop1h 50m
Deal found 8/12![Porter Airlines logo]()
$233
This Kissandfly.com deal was found by Cheapflights users on 8/14. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:15 pm -
Nonstop1h 46m
Mon 9/148:50 am -
Nonstop2h 03m
Deal found 8/14![Air Canada logo]()
$234
This Mytrip deal was found by Cheapflights users on 8/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:20 pm -
Nonstop1h 40m
Mon 9/1410:10 am -
Nonstop1h 50m
Deal found 8/16![Multiple Airlines logo]()
$235
This Mytrip deal was found by Cheapflights users on 8/14. 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 9/128:45 am -
1 stop6h 05m
Mon 9/147:35 pm -
Nonstop2h 06m
Deal found 8/14![Air Canada logo]()
$235
This Mytrip deal was found by Cheapflights users on 8/14. 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.
Wed 9/92:00 pm -
Nonstop1h 42m
Fri 9/117:35 pm -
Nonstop2h 06m
Deal found 8/14![Air Canada logo]()
$236
This Flightnetwork deal was found by Cheapflights users on 8/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:45 am -
1 stop5h 48m
Sun 9/1312:25 pm -
Nonstop1h 58m
Deal found 8/16![Air Canada logo]()
$236
This Super.com deal was found by Cheapflights users on 8/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:25 am -
Nonstop1h 40m
Wed 9/1610:10 am -
Nonstop1h 50m
Deal found 8/12![Porter Airlines logo]()
$237
This Mytrip deal was found by Cheapflights users on 8/12. 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.
Thu 9/102:00 pm -
Nonstop1h 42m
Sun 9/1312:15 pm -
Nonstop2h 06m
Deal found 8/12![Air Canada logo]()
$237
This Jetabroad deal was found by Cheapflights users on 8/13. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:45 am -
1 stop5h 48m
Fri 9/112:00 pm -
Nonstop1h 55m
Deal found 8/13![Air Canada logo]()
$237
This United deal was found by Cheapflights users on 8/17. 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.
Tue 9/228:50 am -
Nonstop1h 59m
Tue 9/223:00 pm -
1 stop6h 12m
Deal found 8/17![Multiple Airlines logo]()
$238
This Booking.com deal was found by Cheapflights users on 8/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:05 am -
1 stop5h 28m
Tue 9/154:00 pm -
1 stop5h 12m
Deal found 8/16![Air Canada logo]()
$239
This SmartFares deal was found by Cheapflights users on 8/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:25 am -
Nonstop1h 42m
Sat 9/1910:45 am -
1 stop5h 07m
Deal found 8/12![Air Canada logo]()
$242
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 August 17, 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 August 17, 2026.
This FlightHub deal was found by Cheapflights users on 8/16. 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 9/1711:45 am -
Nonstop1h 40m
Tue 9/2210:10 am -
Nonstop1h 50m
Deal found 8/16![Porter Airlines logo]()
$245
This FlightHub deal was found by Cheapflights users on 8/14. 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.
Mon 9/143:20 pm -
Nonstop1h 40m
Thu 9/171:45 pm -
Nonstop1h 50m
Deal found 8/14![Multiple Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Sun 9/135:00 am -
1 stop5h 43m
Fri 9/258:50 am -
Nonstop1h 58m
Deal found 8/15![United Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 8/15. 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.
Sat 9/125:37 pm -
1 stop4h 22m
Wed 9/166:00 am -
1 stop4h 07m
Deal found 8/15![Delta logo]()
$279
This KAYAK deal was found by Cheapflights users on 8/13. 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.
Tue 9/810:40 am -
1 stop6h 40m
Sat 9/1212:15 pm -
Nonstop2h 06m
Deal found 8/13![Air Canada logo]()
$358
This FlightHub deal was found by Cheapflights users on 8/16. 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.
Tue 9/811:45 am -
Nonstop1h 40m
Wed 9/910:10 am -
Nonstop1h 50m
Deal found 8/16![Porter Airlines logo]()
$245
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 9/1012:55 pm -
1 stop5h 07m
Sun 9/138:50 am -
Nonstop2h 03m
Deal found 8/16![United Airlines logo]()
$264
This Justfly.com deal was found by Cheapflights users on 8/16. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:45 am -
Nonstop1h 40m
Sun 9/2710:10 am -
Nonstop1h 50m
Deal found 8/16![Porter Airlines logo]()
$245
This United deal was found by Cheapflights users on 8/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:45 am -
1 stop4h 34m
Tue 9/224:00 pm -
1 stop5h 12m
Deal found 8/13![Multiple Airlines logo]()
$278
This Porter Airlines deal was found by Cheapflights users on 8/12. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:20 pm -
Nonstop1h 40m
Sun 9/2710:10 am -
Nonstop1h 50m
Deal found 8/12![Porter Airlines logo]()
$245
This United deal was found by Cheapflights users on 8/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:25 am -
1 stop6h 54m
Wed 9/238:05 am -
1 stop7h 47m
Deal found 8/13![Multiple Airlines logo]()
$278
This Porter Airlines deal was found by Cheapflights users on 8/16. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:45 am -
Nonstop1h 40m
Sun 9/201:45 pm -
Nonstop1h 50m
Deal found 8/16![Porter Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 8/15. 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 8/319:24 am -
1 stop4h 56m
Tue 9/1512:08 pm -
1 stop7h 25m
Deal found 8/15![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/15. 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 10/238:40 am -
Nonstop3h 48m
Mon 10/2612:37 pm -
Nonstop3h 33m
Deal found 8/15![United Airlines logo]()
$324
This KAYAK deal was found by Cheapflights users on 8/13. 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.
Tue 9/89:18 pm -
Nonstop1h 41m
Thu 9/108:05 am -
Nonstop1h 55m
Deal found 8/13![Air Canada logo]()
$361
This Delta deal was found by Cheapflights users on 8/15. 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.
Sat 8/299:24 am -
1 stop7h 00m
Fri 9/1812:08 pm -
1 stop7h 25m
Deal found 8/15![Delta logo]()
$333
This Trip.com deal was found by Cheapflights users on 8/16. 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 9/303:20 pm -
Nonstop1h 40m
Wed 10/710:10 am -
Nonstop1h 50m
Deal found 8/16![Porter Airlines logo]()
$251
This KAYAK deal was found by Cheapflights users on 8/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:40 am -
1 stop6h 40m
Fri 9/1112:15 pm -
Nonstop2h 06m
Deal found 8/12![Air Canada logo]()
$368
This FlightHub deal was found by Cheapflights users on 8/16. 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 9/253:20 pm -
Nonstop1h 40m
Tue 10/2010:10 am -
Nonstop1h 50m
Deal found 8/16![Porter Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 8/13. 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.
Thu 9/241:55 pm -
1 stop8h 04m
Tue 9/299:45 am -
1 stop7h 28m
Deal found 8/13![Delta logo]()
$339
This United deal was found by Cheapflights users on 8/14. 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.
Tue 9/88:45 am -
1 stop4h 55m
Tue 9/86:30 pm -
Nonstop2h 42m
Deal found 8/14![Multiple Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sun 8/307:46 pm -
Nonstop3h 51m
Fri 9/48:30 am -
Nonstop3h 35m
Deal found 8/14![United Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 8/15. 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.
Sun 9/139:29 am -
1 stop6h 51m
Wed 9/1612:08 pm -
1 stop7h 25m
Deal found 8/15![Delta logo]()
$339
This iWofly deal was found by Cheapflights users on 8/13. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2711:45 am -
Nonstop1h 40m
Sun 10/41:45 pm -
Nonstop1h 50m
Deal found 8/13![Porter Airlines logo]()
$256
This KAYAK deal was found by Cheapflights users on 8/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:40 am -
1 stop6h 40m
Fri 9/116:50 am -
1 stop5h 31m
Deal found 8/12![Air Canada logo]()
$377
This United deal was found by Cheapflights users on 8/16. 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.
Sat 10/177:11 am -
Nonstop2h 29m
Sat 10/172:30 pm -
1 stop6h 59m
Deal found 8/16![Multiple Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/87:25 am -
Nonstop1h 42m
Fri 9/1112:15 pm -
Nonstop2h 06m
Deal found 8/12![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 8/15. 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 9/29:24 am -
1 stop7h 00m
Wed 9/1612:08 pm -
1 stop7h 25m
Deal found 8/15![Delta logo]()
$347
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:20 pm -
Nonstop1h 40m
Mon 10/51:45 pm -
Nonstop1h 50m
Deal found 8/14![Porter Airlines logo]()
$261
This KAYAK deal was found by Cheapflights users on 8/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:30 am -
2 stops10h 50m
Thu 9/1010:20 am -
2 stops9h 23m
Deal found 8/12![Air Canada logo]()
$392
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated August 17, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:25 am -
Nonstop1h 40m
Wed 9/1610:10 am -
Nonstop1h 50m
Deal found 8/12![Porter Airlines logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:20 pm -
Nonstop1h 40m
Thu 9/1710:10 am -
Nonstop1h 50m
Deal found 8/12![Porter Airlines logo]()
$233
This Mytrip deal was found by Cheapflights users on 8/14. 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.
Wed 9/92:00 pm -
Nonstop1h 42m
Fri 9/117:35 pm -
Nonstop2h 06m
Deal found 8/14![Air Canada logo]()
$236
This Flightnetwork deal was found by Cheapflights users on 8/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:45 am -
1 stop5h 48m
Sun 9/1312:25 pm -
Nonstop1h 58m
Deal found 8/16![Air Canada logo]()
$236
This Air Canada deal was found by Cheapflights users on 8/12. 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.
Wed 9/911:05 am -
1 stop5h 28m
Sat 9/124:00 pm -
1 stop5h 12m
Deal found 8/12![Air Canada logo]()
$237
This Booking.com deal was found by Cheapflights users on 8/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:05 am -
1 stop5h 28m
Tue 9/154:00 pm -
1 stop5h 12m
Deal found 8/16![Air Canada logo]()
$239
This Flightnetwork deal was found by Cheapflights users on 8/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:45 am -
1 stop5h 48m
Fri 9/114:00 pm -
Nonstop1h 58m
Deal found 8/14![Air Canada logo]()
$241
This Kissandfly.com deal was found by Cheapflights users on 8/14. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:15 pm -
Nonstop1h 46m
Mon 9/148:50 am -
Nonstop2h 03m
Deal found 8/14![Air Canada logo]()
$234
This Mytrip deal was found by Cheapflights users on 8/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:20 pm -
Nonstop1h 40m
Mon 9/1410:10 am -
Nonstop1h 50m
Deal found 8/16![Multiple Airlines logo]()
$235
This Mytrip deal was found by Cheapflights users on 8/12. 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.
Thu 9/102:00 pm -
Nonstop1h 42m
Sun 9/1312:15 pm -
Nonstop2h 06m
Deal found 8/12![Air Canada logo]()
$237
This Mytrip deal was found by Cheapflights users on 8/14. 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 9/128:45 am -
1 stop6h 05m
Mon 9/147:35 pm -
Nonstop2h 06m
Deal found 8/14![Air Canada logo]()
$235
This United deal was found by Cheapflights users on 8/17. 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.
Tue 9/228:50 am -
Nonstop1h 59m
Tue 9/223:00 pm -
1 stop6h 12m
Deal found 8/17![Multiple Airlines logo]()
$238
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 August 17, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Super.com deal was found by Cheapflights users on 8/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:20 pm -
Nonstop1h 40m
Deal found 8/14![Air Transat logo]()
$104
This Air Canada deal was found by Cheapflights users on 8/12. 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.
Tue 9/153:40 pm -
1 stop5h 13m
Deal found 8/12![Air Canada logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Thu 9/177:11 am -
1 stop12h 44m
Deal found 8/12![Multiple Airlines logo]()
$105
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/812:59 pm -
Nonstop1h 47m
Deal found 8/12![United Airlines logo]()
$106
This Trip.com deal was found by Cheapflights users on 8/13. 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.
Thu 9/33:20 pm -
Nonstop1h 40m
Deal found 8/13![Porter Airlines logo]()
$108
This Air Canada deal was found by Cheapflights users on 8/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:45 am -
1 stop6h 05m
Deal found 8/13![Air Canada logo]()
$109
This Air Canada deal was found by Cheapflights users on 8/12. 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.
Mon 9/1411:05 am -
1 stop6h 07m
Deal found 8/12![Air Canada logo]()
$109
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:55 am -
1 stop7h 25m
Deal found 8/14![Delta logo]()
$111
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/279:29 am -
1 stop6h 51m
Deal found 8/14![Delta logo]()
$111
This Air Canada deal was found by Cheapflights users on 8/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:25 am -
Nonstop1h 42m
Deal found 8/14![Air Canada logo]()
$112
This Air Canada deal was found by Cheapflights users on 8/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:40 pm -
Nonstop1h 46m
Deal found 8/14![Air Canada logo]()
$112
This Air Canada deal was found by Cheapflights users on 8/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/272:00 pm -
Nonstop1h 42m
Deal found 8/14![Air Canada logo]()
$113
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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Cheapflightsfares) |
One-way from | $104 (Super.com) |
Popular in | April |
Cheapest in | March |
Average price | $310 |
Good round-trip deal | $243 or less |
Good one-way deal | $111 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 2,558,603 searches. Data last updated August 17, 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
Quickest round-trip
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Thu 9/17
11:45 am-2:25 pm
Nonstop1h 40m
Toronto Island
Tue 9/22
10:10 am-11:00 am
Nonstop1h 50m
$245
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Tue 9/8
11:45 am-2:25 pm
Nonstop1h 40m
Toronto Island
Wed 9/9
10:10 am-11:00 am
Nonstop1h 50m
$245
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Fri 9/25
11:45 am-2:25 pm
Nonstop1h 40m
Toronto Island
Sun 9/27
10:10 am-11:00 am
Nonstop1h 50m
$245
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Wed 9/23
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Sun 9/27
10:10 am-11:00 am
Nonstop1h 50m
$245
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Wed 9/16
11:45 am-2:25 pm
Nonstop1h 40m
Toronto Island
Sun 9/20
1:45 pm-2:35 pm
Nonstop1h 50m
$245
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Wed 9/30
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Wed 10/7
10:10 am-11:00 am
Nonstop1h 50m
$251
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Fri 9/25
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Tue 10/20
10:10 am-11:00 am
Nonstop1h 50m
$254
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Sun 9/27
11:45 am-2:25 pm
Nonstop1h 40m
Toronto Island
Sun 10/4
1:45 pm-2:35 pm
Nonstop1h 50m
$256
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Mon 9/14
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Thu 9/17
1:45 pm-2:35 pm
Nonstop1h 50m
$259
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Mon 9/28
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Mon 10/5
1:45 pm-2:35 pm
Nonstop1h 50m
$261
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
ORD-YTZ
MDW-YYZ
ORD-YUL
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
ORD-YTZ
MDW-YYZ
What is the cheapest month to book a flight from Chicago to Canada?
Currently, November is the cheapest month in which you can book a flight from Chicago to Canada (average of $317). Flying from Chicago to Canada in July is currently the most expensive (average of $444). 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 August 17, 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 18% 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 August 17, 2026.
The most flights from CHI to CA0 are scheduled on a Friday (70 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (57 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 62 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 August 15, 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 August 17, 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.
Boarding
8.2
Overall
8.0
Food
7.6
Comfort
8.0
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Boarding
8.2
Overall
8.0
Food
7.6
Comfort
8.0
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Boarding
8.2
Overall
8.0
Food
7.6
Comfort
8.0
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Boarding
8.2
Overall
8.0
Food
7.6
Comfort
8.0
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Boarding
8.2
Overall
8.0
Food
7.6
Comfort
8.0
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Boarding
8.2
Overall
8.0
Food
7.6
Comfort
8.0
Crew
8.6
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - 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 August 17, 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 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$315 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$404 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$123 | Average$567 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$347 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$160 | Average$340 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$199 | Average$489 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$217 | Average$343 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$381 | Average$385 | FlexibilityNo cancel fee | On-time68% |