$102+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Oct 1 — Oct 81
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 1, 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 1, 2026.
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/243:20 pm -
Nonstop1h 40m
Sun 9/2710:10 am -
Nonstop1h 50m
Deal found 9/1![Porter Airlines logo]()
$228
This Air Canada deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/242:00 pm -
Nonstop1h 48m
Sat 10/316:45 am -
1 stop5h 22m
Deal found 9/1![Air Canada logo]()
$230
This United deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/3012:59 pm -
Nonstop1h 47m
Wed 10/72:00 pm -
Nonstop1h 55m
Deal found 8/31![Multiple Airlines logo]()
$230
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:45 am -
1 stop8h 12m
Fri 10/2311:55 pm -
1 stop8h 05m
Deal found 9/1![Air Canada logo]()
$232
This Booking.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/17:25 am -
Nonstop1h 48m
Mon 10/512:20 pm -
2 stops8h 52m
Deal found 9/1![Air Canada logo]()
$232
This Kissandfly.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Fri 9/188:40 pm -
Nonstop1h 46m
Sun 9/208:50 am -
Nonstop2h 03m
Deal found 8/28![Air Canada logo]()
$232
This FlightHub deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2511:45 am -
Nonstop1h 40m
Fri 10/21:45 pm -
Nonstop1h 50m
Deal found 8/27![Multiple Airlines logo]()
$233
This Booking.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/298:45 am -
1 stop6h 05m
Tue 10/67:35 pm -
Nonstop2h 10m
Deal found 9/1![Air Canada logo]()
$233
This Kissandfly.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:45 am -
1 stop7h 08m
Sun 9/207:00 am -
Nonstop2h 00m
Deal found 8/29![Air Canada logo]()
$233
This oojo deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:20 pm -
Nonstop1h 40m
Mon 9/281:45 pm -
Nonstop1h 50m
Deal found 8/28![Porter Airlines logo]()
$234
This Kissandfly.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/2412:59 pm -
Nonstop1h 47m
Sun 9/277:00 am -
Nonstop2h 00m
Deal found 8/31![Lufthansa logo]()
$234
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/27:25 am -
Nonstop1h 42m
Sun 10/412:15 pm -
Nonstop2h 06m
Deal found 8/27![Air Canada logo]()
$237
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 1, 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 1, 2026.
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/243:20 pm -
Nonstop1h 40m
Sun 9/2710:10 am -
Nonstop1h 50m
Deal found 9/1![Porter Airlines logo]()
$228
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/159:20 pm -
Nonstop1h 39m
Sun 10/182:45 pm -
Nonstop2h 06m
Deal found 8/31![United Airlines logo]()
$230
This United deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:55 pm -
1 stop9h 59m
Sun 9/278:05 am -
Nonstop1h 55m
Deal found 8/27![Multiple Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/188:55 am -
1 stop7h 25m
Mon 9/212:24 pm -
1 stop7h 06m
Deal found 8/28![Delta logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/2011:45 am -
Nonstop1h 40m
Wed 9/231:45 pm -
Nonstop1h 50m
Deal found 8/31![Air Transat logo]()
$286
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/127:25 am -
1 stop5h 20m
Wed 9/167:30 am -
1 stop6h 51m
Deal found 8/27![Air Canada logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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.
Fri 10/236:00 am -
1 stop6h 52m
Mon 10/265:25 pm -
2 stops17h 53m
Deal found 8/29![Alaska Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/236:30 am -
1 stop6h 49m
Wed 9/3011:00 am -
Nonstop2h 00m
Deal found 8/31![United Airlines logo]()
$240
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Wed 9/163:20 pm -
Nonstop1h 40m
Sat 9/191:45 pm -
Nonstop1h 50m
Deal found 8/28![Porter Airlines logo]()
$268
This United deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/28:40 am -
Nonstop3h 48m
Sat 10/101:00 am -
1 stop8h 17m
Deal found 9/1![Multiple Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/247:05 am -
1 stop7h 10m
Sun 9/272:24 pm -
1 stop7h 06m
Deal found 8/31![Delta logo]()
$279
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Wed 9/1611:45 am -
Nonstop1h 40m
Sun 9/2010:10 am -
Nonstop1h 50m
Deal found 8/27![Porter Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/196:40 pm -
1 stop3h 19m
Sun 9/2012:08 pm -
1 stop7h 25m
Deal found 8/29![Delta logo]()
$279
This United deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/510:43 am -
Nonstop1h 59m
Wed 10/73:30 pm -
1 stop5h 42m
Deal found 8/27![Multiple Airlines logo]()
$282
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Tue 9/293:20 pm -
Nonstop1h 40m
Fri 10/21:45 pm -
Nonstop1h 50m
Deal found 8/28![Porter Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/249:29 am -
1 stop6h 51m
Sun 9/276:00 am -
1 stop4h 07m
Deal found 8/31![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/2012:59 pm -
Nonstop1h 47m
Mon 9/219:00 pm -
Nonstop2h 05m
Deal found 8/31![United Airlines logo]()
$315
This United deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/22:37 pm -
1 stop8h 17m
Sun 10/411:10 pm -
1 stop12h 07m
Deal found 8/27![Multiple Airlines logo]()
$322
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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
Sun 10/410:10 am -
Nonstop1h 50m
Deal found 9/1![Porter Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 12/32:04 pm -
1 stop11h 17m
Sun 12/68:45 am -
2 stops8h 41m
Deal found 9/1![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/269:20 pm -
Nonstop1h 39m
Mon 9/287:00 am -
Nonstop2h 00m
Deal found 8/31![United Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/206:10 pm -
Nonstop1h 40m
Sun 11/224:35 pm -
Nonstop1h 55m
Deal found 8/27![Porter Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/21:55 pm -
1 stop8h 04m
Sun 10/412:08 pm -
1 stop7h 18m
Deal found 8/27![Delta logo]()
$299
This United deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/298:40 am -
Nonstop4h 55m
Mon 11/301:45 am -
1 stop8h 22m
Deal found 8/27![Multiple Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/259:20 pm -
Nonstop1h 39m
Mon 9/289:00 pm -
Nonstop2h 06m
Deal found 8/31![United Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/2412:59 pm -
Nonstop1h 47m
Mon 9/287:00 am -
Nonstop2h 00m
Deal found 8/28![United Airlines logo]()
$334
This United deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/217:45 pm -
Nonstop3h 50m
Wed 9/306:00 am -
1 stop7h 52m
Deal found 8/29![Multiple Airlines logo]()
$337
This FlightHub deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/811:45 am -
Nonstop1h 40m
Tue 10/131:45 pm -
Nonstop1h 50m
Deal found 8/27![Porter Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:03 pm -
1 stop11h 14m
Fri 11/278:45 am -
2 stops10h 32m
Deal found 8/30![Delta logo]()
$334
This United deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/58:40 am -
Nonstop3h 48m
Sat 10/107:10 am -
1 stop8h 43m
Deal found 8/30![Multiple Airlines logo]()
$343
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated September 1, 2026 and is based on user searches.
This Kissandfly.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Fri 9/188:40 pm -
Nonstop1h 46m
Sun 9/208:50 am -
Nonstop2h 03m
Deal found 8/28![Air Canada logo]()
$232
This Kissandfly.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:45 am -
1 stop7h 08m
Sun 9/207:00 am -
Nonstop2h 00m
Deal found 8/29![Air Canada logo]()
$233
This oojo deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:20 pm -
Nonstop1h 40m
Mon 9/281:45 pm -
Nonstop1h 50m
Deal found 8/28![Porter Airlines logo]()
$234
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/243:20 pm -
Nonstop1h 40m
Sun 9/2710:10 am -
Nonstop1h 50m
Deal found 9/1![Porter Airlines logo]()
$228
This Kissandfly.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/2412:59 pm -
Nonstop1h 47m
Sun 9/277:00 am -
Nonstop2h 00m
Deal found 8/31![Lufthansa logo]()
$234
This FlightHub deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2511:45 am -
Nonstop1h 40m
Fri 10/21:45 pm -
Nonstop1h 50m
Deal found 8/27![Multiple Airlines logo]()
$233
This Booking.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/298:45 am -
1 stop6h 05m
Tue 10/67:35 pm -
Nonstop2h 10m
Deal found 9/1![Air Canada logo]()
$233
This United deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/3012:59 pm -
Nonstop1h 47m
Wed 10/72:00 pm -
Nonstop1h 55m
Deal found 8/31![Multiple Airlines logo]()
$230
This Booking.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/17:25 am -
Nonstop1h 48m
Mon 10/512:20 pm -
2 stops8h 52m
Deal found 9/1![Air Canada logo]()
$232
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/27:25 am -
Nonstop1h 42m
Sun 10/412:15 pm -
Nonstop2h 06m
Deal found 8/27![Air Canada logo]()
$237
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:45 am -
1 stop8h 12m
Fri 10/2311:55 pm -
1 stop8h 05m
Deal found 9/1![Air Canada logo]()
$232
This Air Canada deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/242:00 pm -
Nonstop1h 48m
Thu 10/299:45 am -
1 stop6h 07m
Deal found 9/1![Air Canada logo]()
$230
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 1, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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
Deal found 8/31![United Airlines logo]()
$102
This Trip.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/183:20 pm -
Nonstop1h 40m
Deal found 8/27![Porter Airlines logo]()
$103
This Air Canada deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/222:00 pm -
Nonstop1h 42m
Deal found 9/1![Air Canada logo]()
$103
This Air Canada deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/38:45 am -
2 stops7h 22m
Deal found 9/1![Air Canada logo]()
$103
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/263:40 pm -
1 stop5h 13m
Deal found 8/27![Air Canada logo]()
$104
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/168:45 am -
1 stop6h 05m
Deal found 8/31![Air Canada logo]()
$105
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/113:40 pm -
1 stop5h 13m
Deal found 8/27![Air Canada logo]()
$105
This Justfly.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:45 am -
Nonstop1h 40m
Deal found 9/1![Air Transat logo]()
$106
This Trip.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/112:00 pm -
Nonstop1h 53m
Deal found 8/28![Air Canada logo]()
$107
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/218:45 am -
1 stop6h 05m
Deal found 8/31![Air Canada logo]()
$109
This Air Canada deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/273:40 pm -
1 stop5h 13m
Deal found 8/28![Air Canada logo]()
$109
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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
Deal found 8/27![United Airlines logo]()
$110
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 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $228 (Trip.com) |
One-way from | $102 (United Airlines) |
Popular in | August |
Cheapest in | March |
Average price | $272 |
Good round-trip deal | $207 or less |
Good one-way deal | $135 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 1, 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 9/24
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Sun 9/27
10:10 am-11:00 am
Nonstop1h 50m
$228
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Thu 10/15
9:20 pm-11:59 pm
Nonstop1h 39m
Toronto Pearson Intl
Sun 10/18
2:45 pm-3:51 pm
Nonstop2h 06m
$230
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Wed 9/23
6:30 am-2:19 pm
1 stop6h 49m
Toronto Pearson Intl
Wed 9/30
11:00 am-12:00 pm
Nonstop2h 00m
$240
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Thu 9/24
12:55 pm-11:54 pm
1 stop9h 59m
Toronto Pearson Intl
Sun 9/27
8:05 am-9:00 am
Nonstop1h 55m
$264
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Wed 9/16
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Sat 9/19
1:45 pm-2:35 pm
Nonstop1h 50m
$268
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
10:10 am-11:00 am
Nonstop1h 50m
$271
ChicagoToronto
MDW Chicago Midway - YTZ Toronto Island
MDWYTZ
Chicago Midway
Tue 9/29
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Fri 10/2
1:45 pm-2:35 pm
Nonstop1h 50m
$272
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Fri 10/2
8:40 am-11:28 am
Nonstop3h 48m
Calgary
Sat 10/10
1:00 am-10:17 am
1 stop8h 17m
$273
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Fri 9/18
8:55 am-5:20 pm
1 stop7h 25m
Toronto Pearson Intl
Mon 9/21
2:24 pm-8:30 pm
1 stop7h 06m
$279
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Thu 9/24
7:05 am-3:15 pm
1 stop7h 10m
Toronto Pearson Intl
Sun 9/27
2:24 pm-8:30 pm
1 stop7h 06m
$279
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-YUL
ORD-YVR
ORD-YYC
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-YUL
ORD-YVR
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 $332). Flying from Chicago to Canada in July is currently the most expensive (average of $443). 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 1, 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 15% 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 1, 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 (32 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 137 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 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 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 29, 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 1, 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.
Comfort
8.0
Crew
8.6
Food
7.6
Entertainment
6.9
Boarding
8.2
Overall
8.0
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Comfort
8.0
Crew
8.6
Food
7.6
Entertainment
6.9
Boarding
8.2
Overall
8.0
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Comfort
8.0
Crew
8.6
Food
7.6
Entertainment
6.9
Boarding
8.2
Overall
8.0
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Comfort
8.0
Crew
8.6
Food
7.6
Entertainment
6.9
Boarding
8.2
Overall
8.0
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Comfort
8.0
Crew
8.6
Food
7.6
Entertainment
6.9
Boarding
8.2
Overall
8.0
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Comfort
8.0
Crew
8.6
Food
7.6
Entertainment
6.9
Boarding
8.2
Overall
8.0
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 September 1, 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 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$315 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$432 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$123 | Average$571 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$357 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$160 | Average$338 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$208 | Average$523 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$217 | Average$343 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$381 | Average$385 | FlexibilityNo cancel fee | On-time68% |