$130+ Cheap flights from Canada to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from Canada to Chicago 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 Canada to Chicago
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Cheapest flights from Canada to ChicagoExplore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
Explore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
This Trip.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:25 pm -
Nonstop1h 58m
Sat 10/109:55 am -
Nonstop1h 45m
Deal found 9/12![Air Canada logo]()
$198
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
Nonstop2h 00m
Sun 10/259:21 pm -
Nonstop1h 38m
Deal found 9/11![United Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:45 pm -
Nonstop1h 50m
Mon 10/53:20 pm -
Nonstop1h 40m
Deal found 9/11![Porter Airlines logo]()
$205
This Trip.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:45 am -
1 stop5h 07m
Sun 10/48:45 am -
1 stop6h 05m
Deal found 9/14![Air Canada logo]()
$205
This Air Canada deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/106:50 pm -
Nonstop1h 58m
Fri 10/3012:50 pm -
Nonstop1h 43m
Deal found 9/10![Air Canada logo]()
$206
This Mytrip deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:10 am -
Nonstop1h 50m
Wed 10/1411:45 am -
Nonstop1h 40m
Deal found 9/12![Porter Airlines logo]()
$207
This Kissandfly.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:35 pm -
Nonstop2h 06m
Sun 9/277:25 am -
Nonstop1h 42m
Deal found 9/11![Air Canada logo]()
$207
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:50 pm -
Nonstop1h 58m
Mon 9/283:40 pm -
1 stop6h 38m
Deal found 9/10![Air Canada logo]()
$208
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:45 pm -
Nonstop1h 50m
Sun 10/183:20 pm -
Nonstop1h 40m
Deal found 9/10![Porter Airlines logo]()
$208
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:00 pm -
Nonstop1h 58m
Sun 9/2711:05 am -
1 stop5h 28m
Deal found 9/11![Air Canada logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Wed 10/73:20 pm -
Nonstop1h 40m
Deal found 9/11![Porter Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sun 10/43:20 pm -
Nonstop1h 40m
Deal found 9/11![Porter Airlines logo]()
$210
Best flights from Canada to ChicagoDiscover carefully curated flight deals from Canada to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
Discover carefully curated flight deals from Canada to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
This United deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:50 am -
Nonstop1h 58m
Tue 9/299:55 am -
Nonstop1h 45m
Deal found 9/11![Multiple Airlines logo]()
$205
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:00 am -
Nonstop2h 00m
Wed 10/77:09 am -
Nonstop1h 45m
Deal found 9/13![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:45 am -
1 stop3h 54m
Fri 10/29:29 am -
1 stop6h 51m
Deal found 9/13![Delta logo]()
$238
This Trip.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:10 am -
Nonstop1h 50m
Thu 10/811:45 am -
Nonstop1h 40m
Deal found 9/13![Porter Airlines logo]()
$260
This deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Wed 9/3012:15 pm -
Nonstop2h 06m
Sat 3/207:25 am -
Nonstop1h 41m
Deal found 9/10![Air Canada logo]()
$264
This Alaska Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:55 pm -
1 stop9h 04m
Tue 12/86:00 am -
1 stop9h 35m
Deal found 9/13![Alaska Airlines logo]()
$348
This United deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:35 pm -
Nonstop2h 09m
Tue 11/310:15 am -
Nonstop1h 37m
Deal found 9/11![Multiple Airlines logo]()
$205
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:45 am -
Nonstop2h 09m
Thu 11/59:21 pm -
Nonstop1h 38m
Deal found 9/13![United Airlines logo]()
$205
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:50 am -
Nonstop1h 58m
Sat 10/179:20 pm -
Nonstop1h 39m
Deal found 9/12![United Airlines logo]()
$205
This United deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:00 pm -
Nonstop2h 06m
Sun 9/2711:05 am -
1 stop6h 48m
Deal found 9/11![Multiple Airlines logo]()
$213
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/812:10 pm -
1 stop6h 50m
Wed 11/111:31 pm -
1 stop8h 26m
Deal found 9/12![Delta logo]()
$238
This United deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:00 am -
Nonstop2h 00m
Sat 10/243:40 pm -
1 stop7h 13m
Deal found 9/14![Multiple Airlines logo]()
$213
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am -
Nonstop2h 00m
Mon 10/55:00 am -
1 stop5h 43m
Deal found 9/12![United Airlines logo]()
$214
This Trip.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:45 pm -
Nonstop1h 50m
Mon 9/2811:45 am -
Nonstop1h 40m
Deal found 9/12![Porter Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:10 pm -
1 stop6h 50m
Tue 11/106:44 pm -
1 stop3h 13m
Deal found 9/14![Delta logo]()
$238
This Porter Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:35 am -
Nonstop2h 05m
Mon 11/26:20 pm -
Nonstop1h 46m
Deal found 9/12![Porter Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:45 am -
1 stop4h 06m
Tue 11/249:30 am -
1 stop3h 00m
Deal found 9/13![Delta logo]()
$238
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:00 am -
Nonstop2h 00m
Sun 10/119:20 pm -
Nonstop1h 39m
Deal found 9/13![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:10 pm -
1 stop6h 50m
Sat 10/179:29 am -
1 stop6h 50m
Deal found 9/12![Delta logo]()
$238
This Porter Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/51:45 pm -
Nonstop1h 50m
Fri 3/55:35 pm -
Nonstop1h 42m
Deal found 9/10![Porter Airlines logo]()
$264
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:26 pm -
Nonstop2h 22m
Mon 11/26:05 pm -
1 stop4h 47m
Deal found 9/13![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 am -
1 stop4h 42m
Sat 11/289:30 am -
1 stop6h 50m
Deal found 9/14![Delta logo]()
$238
This Porter Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Thu 10/11:45 pm -
Nonstop1h 50m
Sun 3/711:15 am -
Nonstop1h 42m
Deal found 9/10![Porter Airlines logo]()
$264
This United deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:37 pm -
Nonstop3h 33m
Thu 11/58:45 am -
1 stop10h 09m
Deal found 9/11![Multiple Airlines logo]()
$266
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
Nonstop2h 00m
Sun 10/119:45 pm -
1 stop11h 19m
Deal found 9/12![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop7h 39m
Mon 10/59:29 am -
1 stop6h 51m
Deal found 9/10![Delta logo]()
$239
This Porter Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Sun 10/410:10 am -
Nonstop1h 50m
Wed 3/311:15 am -
Nonstop1h 42m
Deal found 9/10![Porter Airlines logo]()
$264
This United deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/167:00 am -
1 stop13h 30m
Mon 11/234:30 pm -
1 stop8h 36m
Deal found 9/10![Multiple Airlines logo]()
$271
This Porter Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Sun 10/410:10 am -
Nonstop1h 50m
Thu 3/411:15 am -
Nonstop1h 42m
Deal found 9/10![Porter Airlines logo]()
$264
This United deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/147:00 am -
1 stop13h 30m
Mon 11/234:30 pm -
1 stop8h 36m
Deal found 9/10![Multiple Airlines logo]()
$271
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated September 15, 2026 and is based on user searches.
This Kissandfly.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:35 pm -
Nonstop2h 06m
Sun 9/277:25 am -
Nonstop1h 42m
Deal found 9/11![Air Canada logo]()
$207
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:00 pm -
Nonstop1h 58m
Sun 9/2711:05 am -
1 stop5h 28m
Deal found 9/11![Air Canada logo]()
$209
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:50 pm -
Nonstop1h 58m
Mon 9/283:40 pm -
1 stop6h 38m
Deal found 9/10![Air Canada logo]()
$208
This Trip.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:45 am -
1 stop5h 07m
Sun 10/48:45 am -
1 stop6h 05m
Deal found 9/14![Air Canada logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sat 10/103:20 pm -
Nonstop1h 40m
Deal found 9/11![Porter Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sun 10/43:20 pm -
Nonstop1h 40m
Deal found 9/11![Porter Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:45 pm -
Nonstop1h 50m
Mon 10/53:20 pm -
Nonstop1h 40m
Deal found 9/11![Porter Airlines logo]()
$205
This Trip.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:25 pm -
Nonstop1h 58m
Sat 10/109:55 am -
Nonstop1h 45m
Deal found 9/12![Air Canada logo]()
$198
This Air Canada deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/106:50 pm -
Nonstop1h 58m
Fri 10/3012:50 pm -
Nonstop1h 43m
Deal found 9/10![Air Canada logo]()
$206
This Mytrip deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:10 am -
Nonstop1h 50m
Wed 10/1411:45 am -
Nonstop1h 40m
Deal found 9/12![Porter Airlines logo]()
$207
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:45 pm -
Nonstop1h 50m
Sun 10/183:20 pm -
Nonstop1h 40m
Deal found 9/10![Porter Airlines logo]()
$208
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
Nonstop2h 00m
Sun 10/259:21 pm -
Nonstop1h 38m
Deal found 9/11![United Airlines logo]()
$205
One-way flights from Canada to ChicagoSearch for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:00 pm -
Nonstop2h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$130
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/111:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Porter Airlines logo]()
$130
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/254:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Porter Airlines logo]()
$130
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:05 am -
Nonstop1h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Air Canada logo]()
$131
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Porter Airlines logo]()
$131
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/2710:10 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Porter Airlines logo]()
$132
This FlightHub deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Porter Airlines logo]()
$132
This Flightnetwork deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/256:55 pm -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Air Canada logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Porter Airlines logo]()
$133
This Air Canada deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:20 pm -
2 stops8h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$133
This iWofly deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:05 am -
Nonstop1h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Air Canada logo]()
$134
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Porter Airlines logo]()
$134
Find flight deals from Canada to Chicago
Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Trip.com) |
One-way from | $130 (United Airlines) |
Popular in | October |
Cheapest in | February |
Average price | $280 |
Good round-trip deal | $235 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Canada to Chicago 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 15, 2026.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 11/14
6:45 am-7:54 am
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Tue 11/17
10:53 am-11:57 am
Nonstop2h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
Quickest round-trip
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 10/1
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 10/22
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 10/6
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$136
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Sun 11/1
4:35 pm-5:40 pm
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$136
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Tue 12/1
9:45 am-2:52 pm
1 stop6h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Tue 10/13
12:15 pm-1:25 pm
Nonstop2h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Mon 10/5
9:00 pm-10:06 pm
Nonstop2h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 10/1
7:00 am-8:00 am
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Canada to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada with our price prediction graph.
YYZ-ORD
YYZ-MDW
YTZ-MDW
YTZ-ORD
YVR-ORD
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 Canada to Chicago
CA0-CHI
YYZ-ORD
YYZ-MDW
YTZ-MDW
YTZ-ORD
What is the cheapest month to book a flight from Canada to Chicago?
Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of $277). Flying from Canada to Chicago in August is currently the most expensive (average of $362). 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 CA to CHI?
Find hourly flight availability from Canada to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2026.
A simple way to save on the total cost of your ticket is to fly from Canada to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight at noon.
Weekly flight availability from Canada to Chicago
Explore weekly flight availability from Canada to Chicago. 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 15, 2026.
The most flights from CA0 to CHI are scheduled on a Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).
How often are flights from Canada to Chicago delayed?
About 14% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 135 minutes.
What is the most punctual flight time for Canada to Chicago 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?
Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Canada to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.
How far ahead should I book a flight from Canada to Chicago?
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Canada to Chicago. 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 Canada to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Canada to Chicago. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Thursday mornings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 15, 2026.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Entertainment
6.9
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Entertainment
6.9
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Entertainment
6.9
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Entertainment
6.9
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Entertainment
6.9
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Entertainment
6.9
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Related info for your journey
Find useful and relevant information for your journey from Canada to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Canada to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 15, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Canada to Chicago by cabin class
Find flights from Canada to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Canada and Chicago flights
Browse other Canada and Chicago flight options. Last updated on September 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Canada to Chicago flights
Consider these flights traveling from Canada to Chicago.
Top 6 airlines flying from Canada to Chicago
Discover the top 6 airlines that operate flights from Canada to Chicago. 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$480 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$462 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$163 | Average$339 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$167 | Average$405 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$168 | Average$384 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$253 | Average$371 | FlexibilityNo cancel fee | On-timeN/A |