$137+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Nov 12 — Nov 191
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 October 13, 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 October 13, 2026.
This VIAZA deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/138:05 am -
Nonstop2h 03m
Mon 12/148:50 pm -
Nonstop1h 42m
Deal found 10/9![Air Canada logo]()
$221
This VIAZA deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:30 pm -
Nonstop2h 13m
Sun 11/18:45 am -
Nonstop1h 42m
Deal found 10/8![Air Canada logo]()
$222
This VIAZA deal was found by Cheapflights users on 10/12. 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 VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:20 am -
Nonstop2h 03m
Sun 11/298:45 am -
Nonstop1h 42m
Deal found 10/12![Air Canada logo]()
$223
This Kissandfly.com deal was found by Cheapflights users on 10/10. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:55 pm -
Nonstop2h 10m
Sun 11/15:55 am -
1 stop7h 30m
Deal found 10/10![Lufthansa logo]()
$230
This VIAZA deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:15 pm -
Nonstop2h 10m
Fri 10/301:55 pm -
Nonstop1h 47m
Deal found 10/9![Air Canada logo]()
$230
This Kissandfly.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/77:44 pm -
1 stop12h 45m
Sun 11/81:57 pm -
Nonstop1h 50m
Deal found 10/9![Lufthansa logo]()
$232
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/47:44 pm -
1 stop14h 53m
Sat 12/56:17 pm -
Nonstop1h 58m
Deal found 10/9![United Airlines logo]()
$245
This United Airlines deal was found by Cheapflights users on 10/10. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:26 pm -
Nonstop2h 22m
Sat 11/77:00 am -
1 stop9h 49m
Deal found 10/10![United Airlines logo]()
$251
This VIAZA deal was found by Cheapflights users on 10/10. 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 VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2112:10 pm -
1 stop4h 28m
Sun 11/221:55 pm -
1 stop4h 57m
Deal found 10/10![Air Canada logo]()
$251
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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.
Thu 11/54:30 pm -
Nonstop2h 13m
Sun 11/158:45 am -
Nonstop1h 42m
Deal found 10/8![Air Canada logo]()
$261
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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.
Thu 11/2610:45 am -
1 stop5h 17m
Mon 11/301:55 pm -
Nonstop1h 47m
Deal found 10/8![Air Canada logo]()
$261
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/226:45 am -
1 stop5h 22m
Sun 11/297:05 am -
1 stop6h 16m
Deal found 10/8![Air Canada logo]()
$269
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 October 13, 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 October 13, 2026.
This Gotogate deal was found by Cheapflights users on 10/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:30 am -
Nonstop2h 05m
Sun 11/86:20 pm -
Nonstop1h 45m
Deal found 10/11![Porter Airlines logo]()
$285
This Flightnetwork deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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.
Tue 11/248:20 am -
2 stops7h 42m
Tue 12/17:05 am -
2 stops10h 14m
Deal found 10/9![Air Canada logo]()
$285
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:00 am -
1 stop8h 59m
Wed 12/28:39 am -
1 stop3h 56m
Deal found 10/8![Delta logo]()
$290
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Thu 11/56:45 am -
Nonstop2h 09m
Sun 11/88:50 am -
1 stop4h 35m
Deal found 10/11![United Airlines logo]()
$326
This United deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop5h 47m
Tue 11/101:55 pm -
1 stop6h 50m
Deal found 10/13![Multiple Airlines logo]()
$327
This Air Transat deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/2010:30 am -
Nonstop2h 05m
Sat 11/2812:15 pm -
Nonstop1h 45m
Deal found 10/9![Air Transat logo]()
$335
This Justfly.com deal was found by Cheapflights users on 10/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:35 pm -
Nonstop2h 05m
Sun 11/226:20 pm -
Nonstop1h 45m
Deal found 10/10![Porter Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop5h 29m
Sun 11/18:29 am -
1 stop7h 50m
Deal found 10/8![Delta logo]()
$290
This Air Canada deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:05 pm -
Nonstop2h 15m
Tue 12/81:55 pm -
1 stop5h 01m
Deal found 10/12![Air Canada logo]()
$307
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 12/1112:15 pm -
1 stop5h 02m
Sun 12/135:05 pm -
1 stop5h 02m
Deal found 10/8![Delta logo]()
$290
This Trip.com deal was found by Cheapflights users on 10/11. 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.
Wed 11/2510:30 am -
Nonstop2h 05m
Wed 12/212:15 pm -
Nonstop1h 45m
Deal found 10/11![Porter Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:35 am -
Nonstop2h 09m
Mon 11/23:36 pm -
1 stop6h 50m
Deal found 10/9![United Airlines logo]()
$326
This Air Transat deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/224:35 pm -
Nonstop2h 05m
Sun 11/296:20 pm -
Nonstop1h 45m
Deal found 10/11![Air Transat logo]()
$335
This United deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/261:37 pm -
Nonstop2h 33m
Thu 12/38:45 am -
1 stop10h 13m
Deal found 10/8![Multiple Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 10/11. 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 12/45:55 pm -
Nonstop2h 10m
Sun 12/65:55 am -
1 stop4h 53m
Deal found 10/11![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/2012:50 pm -
1 stop8h 27m
Fri 11/2711:19 am -
1 stop7h 28m
Deal found 10/9![Delta logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/244:35 pm -
Nonstop2h 05m
Sun 11/2912:15 pm -
Nonstop1h 45m
Deal found 10/8![Porter Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/2912:55 pm -
1 stop5h 24m
Sun 11/18:50 am -
1 stop4h 35m
Deal found 10/8![United Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 10/12. 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.
Wed 11/187:25 am -
2 stops10h 40m
Mon 11/232:03 pm -
1 stop11h 14m
Deal found 10/12![Delta logo]()
$301
This KAYAK deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:20 pm -
1 stop7h 10m
Thu 11/1210:32 am -
1 stop7h 25m
Deal found 10/9![Multiple Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Wed 11/47:44 pm -
1 stop5h 17m
Wed 11/114:40 pm -
1 stop5h 46m
Deal found 10/11![United Airlines logo]()
$331
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/135:15 am -
1 stop7h 52m
Tue 11/243:40 pm -
1 stop6h 35m
Deal found 10/8![Air Canada logo]()
$403
This Delta deal was found by Cheapflights users on 10/12. 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 11/72:46 pm -
1 stop6h 52m
Sat 11/143:00 pm -
1 stop7h 48m
Deal found 10/12![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/57:44 pm -
1 stop5h 17m
Sat 11/76:07 pm -
1 stop4h 45m
Deal found 10/9![United Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:10 pm -
2 stops24h 20m
Thu 11/196:20 pm -
Nonstop1h 45m
Deal found 10/8![Multiple Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1812:45 pm -
1 stop8h 52m
Mon 2/226:00 am -
1 stop6h 35m
Deal found 10/12![Delta logo]()
$307
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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.
Wed 12/2310:30 am -
Nonstop2h 05m
Tue 12/2912:15 pm -
Nonstop1h 45m
Deal found 10/9![Porter Airlines logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/136:40 pm -
1 stop6h 21m
Sat 11/143:35 pm -
1 stop6h 51m
Deal found 10/8![United Airlines logo]()
$332
This Air Canada deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:55 am -
1 stop5h 07m
Sun 11/157:05 am -
1 stop5h 55m
Deal found 10/12![Air Canada logo]()
$442
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 12/812:41 pm -
1 stop7h 28m
Thu 12/106:49 am -
1 stop9h 44m
Deal found 10/12![Delta logo]()
$307
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated October 13, 2026 and is based on user searches.
This VIAZA deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:15 pm -
Nonstop2h 10m
Fri 10/301:55 pm -
Nonstop1h 47m
Deal found 10/9![Air Canada logo]()
$230
This VIAZA deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:30 pm -
Nonstop2h 13m
Sun 11/18:45 am -
Nonstop1h 42m
Deal found 10/8![Air Canada logo]()
$222
This Kissandfly.com deal was found by Cheapflights users on 10/10. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:55 pm -
Nonstop2h 10m
Sun 11/15:55 am -
1 stop7h 30m
Deal found 10/10![Lufthansa logo]()
$230
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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.
Thu 11/54:30 pm -
Nonstop2h 13m
Sun 11/158:45 am -
Nonstop1h 42m
Deal found 10/8![Air Canada logo]()
$261
This United Airlines deal was found by Cheapflights users on 10/10. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:26 pm -
Nonstop2h 22m
Sat 11/77:00 am -
1 stop9h 49m
Deal found 10/10![United Airlines logo]()
$251
This Kissandfly.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/77:44 pm -
1 stop12h 45m
Sun 11/81:57 pm -
Nonstop1h 50m
Deal found 10/9![Lufthansa logo]()
$232
This VIAZA deal was found by Cheapflights users on 10/10. 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 VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2112:10 pm -
1 stop4h 28m
Sun 11/221:55 pm -
1 stop4h 57m
Deal found 10/10![Air Canada logo]()
$251
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/226:45 am -
1 stop5h 22m
Sun 11/297:05 am -
1 stop6h 16m
Deal found 10/8![Air Canada logo]()
$269
This VIAZA deal was found by Cheapflights users on 10/12. 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 VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:20 am -
Nonstop2h 03m
Sun 11/298:45 am -
Nonstop1h 42m
Deal found 10/12![Air Canada logo]()
$223
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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.
Thu 11/2610:45 am -
1 stop5h 17m
Mon 11/301:55 pm -
Nonstop1h 47m
Deal found 10/8![Air Canada logo]()
$261
This VIAZA deal was found by Cheapflights users on 10/10. 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 VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:10 am -
2 stops8h 52m
Sun 11/298:45 am -
Nonstop1h 42m
Deal found 10/10![Air Canada logo]()
$265
This United Airlines deal was found by Cheapflights users on 10/12. 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 11/277:44 pm -
1 stop5h 17m
Sat 11/287:03 am -
Nonstop1h 44m
Deal found 10/12![United Airlines logo]()
$245
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 October 13, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This VIAZA deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:55 pm -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Air Canada logo]()
$137
This Mytrip deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:35 am -
1 stop16h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$142
This VIAZA deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:15 pm -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Air Canada logo]()
$146
This SmartFares deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:45 pm -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Air Canada logo]()
$155
This SmartFares deal was found by Cheapflights users on 10/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:20 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Air Canada logo]()
$156
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/314:30 pm -
Nonstop2h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Air Canada logo]()
$157
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/316:45 am -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Air Canada logo]()
$157
This Air Canada deal was found by Cheapflights users on 10/10. 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.
Fri 11/64:30 pm -
Nonstop2h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Air Canada logo]()
$162
This Air Canada deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:45 am -
1 stop5h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Air Canada logo]()
$162
This Air Canada deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/256:45 am -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Air Canada logo]()
$163
This SmartFares deal was found by Cheapflights users on 10/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:05 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Air Canada logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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.
Sun 11/14:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Porter Airlines logo]()
$165
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 October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $221 (VIAZA) |
One-way from | $137 (VIAZA) |
Popular in | October |
Cheapest in | February |
Average price | $305 |
Good round-trip deal | $205 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 October 13, 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
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Wed 11/25
10:45 am-3:02 pm
1 stop5h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Thu 11/26
10:45 am-3:02 pm
1 stop5h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sun 12/6
6:00 am-1:56 pm
1 stop8h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Fri 11/13
12:15 pm-6:30 pm
1 stop7h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 11/12
12:15 pm-6:30 pm
1 stop7h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 11/7
12:10 pm-4:26 pm
1 stop5h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Fri 11/13
3:35 pm-4:44 pm
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$178
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 12/12
8:35 am-9:44 am
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$178
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sun 12/13
5:55 pm-7:05 pm
Nonstop2h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$178
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Mon 11/9
7:26 pm-8:48 pm
Nonstop2h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$178
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
YTZ-ORD
YOW-ORD
YUL-ORD
YYC-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
YTZ-ORD
YOW-ORD
YUL-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 $285). Flying from Canada to Chicago in October is currently the most expensive (average of $372). 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 October 13, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.
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 October 13, 2026.
The most flights from CA0 to CHI are scheduled on a Friday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (59 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 134 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 October 3, 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. Monday evenings 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 October 13, 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.
Crew
8.6
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Overall
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Overall
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Overall
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Overall
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Overall
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Entertainment
7.0
Comfort
8.0
Boarding
8.2
Overall
8.0
Food
7.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Related info for your journey
Find useful and relevant information for your journey from 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
Merrillville
Lansing
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 October 13, 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 October 13, 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 October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$513 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$532 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$163 | Average$342 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$185 | Average$384 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$193 | Average$421 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$318 | FlexibilityNo cancel fee | On-timeN/A |