$100+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Nov 18 — Nov 251
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 October 19, 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 October 19, 2026.
This Super.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:20 pm -
Nonstop1h 45m
Wed 11/2510:30 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:15 pm -
Nonstop1h 45m
Thu 12/1010:30 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$248
This deal was found by Cheapflights users on 10/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:15 pm -
Nonstop1h 45m
Wed 11/44:35 pm -
Nonstop2h 05m
Deal found 10/15![Porter Airlines logo]()
$249
This FlightHub deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:15 pm -
Nonstop1h 45m
Wed 11/2510:30 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$260
This Booking.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:50 pm -
Nonstop1h 43m
Mon 11/166:55 pm -
Nonstop2h 03m
Deal found 10/19![Air Canada logo]()
$263
This deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:20 pm -
Nonstop1h 45m
Tue 12/84:35 pm -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$264
This FlightHub deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:20 pm -
Nonstop1h 45m
Mon 11/234:35 pm -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$269
This Booking.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:55 pm -
Nonstop1h 47m
Mon 11/1612:05 pm -
Nonstop2h 15m
Deal found 10/19![Air Canada logo]()
$272
This CheapTickets.ch deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets.ch is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:20 pm -
Nonstop1h 45m
Sat 11/2810:30 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$273
This Flightnetwork deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:45 am -
Nonstop1h 42m
Sun 11/222:35 pm -
Nonstop2h 03m
Deal found 10/19![Air Canada logo]()
$274
This Super.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:15 pm -
Nonstop1h 45m
Sat 11/214:35 pm -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$276
This deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:15 pm -
Nonstop1h 45m
Sat 1/3010:35 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$277
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 October 19, 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 October 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:20 pm -
Nonstop1h 45m
Mon 11/2310:30 am -
Nonstop2h 05m
Deal found 10/17![Porter Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 10/14. 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 11/131:57 pm -
Nonstop1h 50m
Fri 11/137:44 pm -
1 stop5h 17m
Deal found 10/14![United Airlines logo]()
$408
This Air Transat deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:15 pm -
Nonstop1h 45m
Fri 11/2010:30 am -
Nonstop2h 05m
Deal found 10/17![Air Transat logo]()
$409
This Delta deal was found by Cheapflights users on 10/14. 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.
Sat 11/212:44 pm -
1 stop7h 13m
Mon 11/236:00 am -
1 stop8h 59m
Deal found 10/14![Delta logo]()
$409
This United deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:00 am -
1 stop8h 21m
Sat 10/3112:20 am -
1 stop9h 03m
Deal found 10/19![Multiple Airlines logo]()
$457
This Alaska Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:00 am -
1 stop8h 35m
Tue 12/87:00 am -
1 stop6h 21m
Deal found 10/19![Alaska Airlines logo]()
$545
This Air Canada deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:40 pm -
1 stop12h 33m
Wed 11/185:10 am -
1 stop7h 57m
Deal found 10/16![Air Canada logo]()
$667
This American Airlines deal was found by Cheapflights users on 10/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/112:50 pm -
1 stop8h 02m
Mon 11/167:00 am -
1 stop6h 01m
Deal found 10/14![American Airlines logo]()
$706
This Porter Airlines deal was found by Cheapflights users on 10/14. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:20 pm -
Nonstop1h 45m
Fri 12/410:30 am -
Nonstop2h 05m
Deal found 10/14![Porter Airlines logo]()
$393
This Air Transat deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:20 pm -
Nonstop1h 45m
Sun 11/224:35 pm -
Nonstop2h 05m
Deal found 10/17![Air Transat logo]()
$409
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:29 am -
1 stop7h 50m
Mon 11/96:00 am -
1 stop8h 59m
Deal found 10/17![Delta logo]()
$410
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:57 pm -
Nonstop1h 50m
Mon 11/3010:53 am -
Nonstop2h 04m
Deal found 10/19![United Airlines logo]()
$417
This FlightHub deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:15 pm -
Nonstop1h 45m
Fri 11/1310:30 am -
Nonstop2h 05m
Deal found 10/18![Porter Airlines logo]()
$394
This Air Transat deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:15 pm -
Nonstop1h 45m
Mon 11/1610:30 am -
Nonstop2h 05m
Deal found 10/17![Air Transat logo]()
$409
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:05 pm -
1 stop4h 52m
Tue 12/19:45 am -
1 stop5h 11m
Deal found 10/19![Delta logo]()
$410
This Porter Airlines deal was found by Cheapflights users on 10/16. 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.
Tue 11/1712:15 pm -
Nonstop1h 45m
Wed 11/184:35 pm -
Nonstop2h 05m
Deal found 10/16![Porter Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:40 am -
Nonstop4h 55m
Wed 11/181:37 pm -
Nonstop2h 33m
Deal found 10/18![United Airlines logo]()
$434
This Air Transat deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:20 pm -
Nonstop1h 45m
Sun 11/2210:30 am -
Nonstop2h 05m
Deal found 10/17![Air Transat logo]()
$409
This United deal was found by Cheapflights users on 10/14. 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.
Sat 11/285:54 pm -
Nonstop2h 23m
Mon 11/3010:10 am -
1 stop6h 28m
Deal found 10/14![Multiple Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:05 am -
1 stop5h 25m
Sun 11/156:00 am -
1 stop8h 59m
Deal found 10/16![Delta logo]()
$410
This Porter Airlines deal was found by Cheapflights users on 10/16. 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 11/186:20 pm -
Nonstop1h 45m
Thu 11/1910:30 am -
Nonstop2h 05m
Deal found 10/16![Porter Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Wed 12/1610:37 am -
Nonstop2h 23m
Sat 1/94:45 pm -
Nonstop3h 00m
Deal found 10/14![United Airlines logo]()
$441
This Air Transat deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:15 pm -
Nonstop1h 45m
Tue 11/1710:30 am -
Nonstop2h 05m
Deal found 10/17![Air Transat logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 10/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:00 am -
1 stop8h 05m
Wed 1/62:35 pm -
1 stop7h 24m
Deal found 10/17![Alaska Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:05 pm -
1 stop4h 52m
Sun 11/1512:15 pm -
1 stop7h 15m
Deal found 10/15![Delta logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:45 am -
1 stop6h 55m
Thu 12/1011:25 am -
1 stop5h 37m
Deal found 10/19![Multiple Airlines logo]()
$533
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:56 pm -
1 stop7h 57m
Thu 11/261:37 pm -
Nonstop2h 33m
Deal found 10/19![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:29 am -
1 stop7h 51m
Mon 11/239:45 am -
1 stop7h 33m
Deal found 10/15![Delta logo]()
$410
This Alaska Airlines deal was found by Cheapflights users on 10/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/32:03 pm -
2 stops11h 42m
Wed 3/102:35 pm -
2 stops20h 34m
Deal found 10/16![Alaska Airlines logo]()
$560
This Delta deal was found by Cheapflights users on 10/15. 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.
Tue 11/178:29 am -
1 stop7h 51m
Fri 11/206:00 am -
1 stop5h 39m
Deal found 10/15![Delta logo]()
$410
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated October 19, 2026 and is based on user searches.
This deal was found by Cheapflights users on 10/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:15 pm -
Nonstop1h 45m
Wed 11/44:35 pm -
Nonstop2h 05m
Deal found 10/15![Porter Airlines logo]()
$249
This Booking.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:50 pm -
Nonstop1h 43m
Mon 11/166:55 pm -
Nonstop2h 03m
Deal found 10/19![Air Canada logo]()
$263
This Booking.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:55 pm -
Nonstop1h 47m
Mon 11/1612:05 pm -
Nonstop2h 15m
Deal found 10/19![Air Canada logo]()
$272
This FlightHub deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:15 pm -
Nonstop1h 45m
Wed 11/2510:30 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$260
This deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:20 pm -
Nonstop1h 45m
Tue 12/84:35 pm -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$264
This deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:15 pm -
Nonstop1h 45m
Sat 1/3010:35 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$277
This Super.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:20 pm -
Nonstop1h 45m
Wed 11/2510:30 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$240
This Super.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:15 pm -
Nonstop1h 45m
Sat 11/214:35 pm -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$276
This FlightHub deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:20 pm -
Nonstop1h 45m
Mon 11/234:35 pm -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:20 pm -
Nonstop1h 45m
Sun 11/224:35 pm -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$281
This Flightnetwork deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:45 am -
Nonstop1h 42m
Sun 11/222:35 pm -
Nonstop2h 03m
Deal found 10/19![Air Canada logo]()
$274
This CheapTickets.ch deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets.ch is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:20 pm -
Nonstop1h 45m
Sat 11/2810:30 am -
Nonstop2h 05m
Deal found 10/19![Porter Airlines logo]()
$273
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 October 19, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This Super.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:20 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Porter Airlines logo]()
$100
This Trip.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:15 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Porter Airlines logo]()
$105
This Jetabroad deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/266:20 pm -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Porter Airlines logo]()
$108
This Trip.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:20 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Porter Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Sat 12/198:00 pm -
1 stop28h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$124
This FlightHub deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:20 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Porter Airlines logo]()
$124
This FlightHub deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:20 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Air Transat logo]()
$130
This FlightHub deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:15 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Air Transat logo]()
$132
This Porter Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:20 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Porter Airlines logo]()
$136
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:42 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![American Airlines logo]()
$136
This Air Canada deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:55 pm -
1 stop6h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Air Canada logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Mon 1/117:10 am -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$138
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 October 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $240 (Super.com) |
One-way from | $100 (Super.com) |
Popular in | October |
Cheapest in | January |
Average price | $333 |
Good round-trip deal | $267 or less |
Good one-way deal | $95 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 October 19, 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
ORD Chicago O'Hare Intl - YTZ Toronto Island
ORDYTZ
Chicago O'Hare Intl
Tue 11/10
6:20 pm-9:05 pm
Nonstop1h 45m
Toronto Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
ChicagoToronto
ORD Chicago O'Hare Intl - YTZ Toronto Island
ORDYTZ
Chicago O'Hare Intl
Thu 12/3
6:20 pm-9:05 pm
Nonstop1h 45m
Toronto Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
ChicagoToronto
ORD Chicago O'Hare Intl - YTZ Toronto Island
ORDYTZ
Chicago O'Hare Intl
Thu 4/8
6:20 pm-9:06 pm
Nonstop1h 46m
Toronto Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$145
ChicagoToronto
ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl
ORDYYZ
Chicago O'Hare Intl
Wed 11/11
7:05 am-1:30 pm
1 stop5h 25m
Toronto Pearson Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$146
ChicagoToronto
ORD Chicago O'Hare Intl - YTZ Toronto Island
ORDYTZ
Chicago O'Hare Intl
Wed 12/2
12:15 pm-3:00 pm
Nonstop1h 45m
Toronto Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$150
ChicagoMontreal
ORD Chicago O'Hare Intl - YUL Montreal Pierre Elliott Trudeau Intl
ORDYUL
Chicago O'Hare Intl
Tue 1/12
12:20 pm-7:05 pm
1 stop5h 45m
Montreal Pierre Elliott Trudeau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$163
ChicagoMontreal
ORD Chicago O'Hare Intl - YUL Montreal Pierre Elliott Trudeau Intl
ORDYUL
Chicago O'Hare Intl
Mon 1/11
12:20 pm-7:05 pm
1 stop5h 45m
Montreal Pierre Elliott Trudeau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$163
ChicagoToronto
ORD Chicago O'Hare Intl - YTZ Toronto Island
ORDYTZ
Chicago O'Hare Intl
Sun 11/8
6:20 pm-9:05 pm
Nonstop1h 45m
Toronto Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$166
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Thu 12/3
6:47 pm-10:37 pm
1 stop27h 50m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
ChicagoMontreal
ORD Chicago O'Hare Intl - YUL Montreal Pierre Elliott Trudeau Intl
ORDYUL
Chicago O'Hare Intl
Tue 12/8
10:37 am-2:00 pm
Nonstop2h 23m
Montreal Pierre Elliott Trudeau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$172
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.
ORD-YTZ
ORD-YYZ
ORD-YYC
ORD-YUL
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
ORD-YTZ
ORD-YYZ
ORD-YYC
ORD-YUL
What is the cheapest month to book a flight from Chicago to Canada?
Currently, May is the cheapest month in which you can book a flight from Chicago to Canada (average of $346). Flying from Chicago to Canada in July is currently the most expensive (average of $442). 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 October 19, 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 in the afternoon, which can drop the price by up to 6% 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 October 19, 2026.
The most flights from CHI to CA0 are scheduled on a Sunday (68 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (58 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 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 38 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 October 17, 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 October 19, 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.
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Food
7.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Food
7.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Food
7.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Food
7.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Food
7.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Food
7.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Related info for your journey
Find useful and relevant information for your journey from 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 October 19, 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 October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$315 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$528 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$139 | Average$421 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$153 | Average$604 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$160 | Average$352 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$217 | Average$343 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$223 | Average$503 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$381 | Average$385 | FlexibilityNo cancel fee | On-time68% |