$135+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Nov 29 — Dec 61
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
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 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 30, 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 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:35 pm -
Nonstop2h 05m
Mon 11/236:20 pm -
Nonstop1h 45m
Deal found 10/27![Porter Airlines logo]()
$213
This Kissandfly.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.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 10/27![Porter Airlines logo]()
$214
This Trip.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/1910:30 am -
Nonstop2h 05m
Sat 11/216:20 pm -
Nonstop1h 45m
Deal found 10/25![Porter Airlines logo]()
$215
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/204:35 pm -
Nonstop2h 05m
Mon 11/236:20 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$216
This Kissandfly.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Mon 11/164:35 pm -
Nonstop2h 05m
Sun 11/226:20 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$218
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/204:35 pm -
Nonstop2h 05m
Sun 11/226:20 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$220
This SmartFares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Fri 11/208:00 am -
1 stop8h 00m
Tue 11/2410:15 am -
Nonstop1h 37m
Deal found 10/26![Air Canada logo]()
$222
This Kissandfly.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/112:35 pm -
Nonstop2h 03m
Mon 12/1410:05 am -
Nonstop1h 37m
Deal found 10/26![Air Canada logo]()
$223
This SmartFares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Fri 11/204:35 pm -
Nonstop2h 05m
Tue 11/246:20 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$223
This SmartFares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:05 pm -
Nonstop2h 15m
Tue 11/241:55 pm -
Nonstop1h 47m
Deal found 10/27![Air Canada logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/2710:30 am -
Nonstop2h 05m
Wed 12/1612:15 pm -
Nonstop1h 45m
Deal found 10/25![Porter Airlines logo]()
$225
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:30 pm -
Nonstop2h 13m
Mon 11/168:40 pm -
Nonstop1h 43m
Deal found 10/26![Air Canada logo]()
$228
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 30, 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 30, 2026.
This Porter Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1110:29 am -
Nonstop2h 05m
Thu 12/312:15 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$273
This United deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:26 pm -
Nonstop2h 22m
Sun 11/1510:15 am -
Nonstop1h 37m
Deal found 10/28![Multiple Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:55 pm -
Nonstop2h 10m
Mon 11/166:05 pm -
1 stop4h 47m
Deal found 10/28![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:20 pm -
1 stop5h 10m
Sun 11/157:05 am -
1 stop3h 14m
Deal found 10/27![Delta logo]()
$328
This Alaska Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:07 am -
1 stop8h 42m
Mon 12/76:00 am -
1 stop15h 37m
Deal found 10/25![Alaska Airlines logo]()
$330
This KAYAK deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:20 pm -
1 stop7h 10m
Thu 11/1210:32 am -
1 stop7h 25m
Deal found 10/27![Air Canada logo]()
$347
This Porter Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/124:35 pm -
Nonstop2h 05m
Tue 12/112:15 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$273
This Porter Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1010:29 am -
Nonstop2h 05m
Fri 12/46:20 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:55 pm -
Nonstop2h 10m
Mon 11/167:03 am -
Nonstop1h 44m
Deal found 10/28![United Airlines logo]()
$322
This United deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/216:45 am -
Nonstop2h 09m
Mon 11/234:45 pm -
Nonstop1h 40m
Deal found 10/26![Multiple Airlines logo]()
$323
This Porter Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1210:29 am -
Nonstop2h 05m
Fri 12/412:15 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:07 am -
1 stop7h 24m
Tue 12/86:00 am -
1 stop15h 37m
Deal found 10/29![Alaska Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:44 pm -
1 stop7h 21m
Fri 11/133:59 pm -
1 stop6h 49m
Deal found 10/27![Delta logo]()
$336
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/107:26 pm -
Nonstop2h 22m
Wed 11/116:04 am -
1 stop7h 21m
Deal found 10/26![United Airlines logo]()
$323
This United deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/127:44 pm -
1 stop5h 17m
Fri 11/138:45 am -
Nonstop1h 42m
Deal found 10/26![Multiple Airlines logo]()
$323
This Porter Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/124:35 pm -
Nonstop2h 05m
Sat 11/2812:15 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop8h 59m
Wed 11/186:49 am -
1 stop9h 38m
Deal found 10/28![Delta logo]()
$336
This Air Canada deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/2710:45 am -
1 stop5h 17m
Sun 11/297:05 am -
1 stop6h 16m
Deal found 10/25![Air Canada logo]()
$383
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/268:35 am -
Nonstop2h 09m
Sat 11/289:21 pm -
Nonstop1h 38m
Deal found 10/26![United Airlines logo]()
$323
This United deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2610:00 am -
1 stop5h 39m
Sat 11/2812:50 pm -
Nonstop1h 43m
Deal found 10/26![Multiple Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1012:44 pm -
1 stop7h 21m
Thu 11/127:05 am -
1 stop7h 53m
Deal found 10/26![Delta logo]()
$337
This Super.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/74:35 pm -
Nonstop1h 55m
Mon 1/1112:20 pm -
Nonstop1h 40m
Deal found 10/29![Porter Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/207:26 pm -
Nonstop2h 22m
Mon 11/235:00 am -
1 stop5h 48m
Deal found 10/25![United Airlines logo]()
$323
This Kissandfly.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:00 am -
3 stops18h 13m
Sun 11/226:20 pm -
Nonstop1h 45m
Deal found 10/25![Multiple Airlines logo]()
$329
This Air Canada deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 3/232:25 pm -
1 stop7h 27m
Sat 3/273:45 pm -
1 stop6h 04m
Deal found 10/25![Air Canada logo]()
$412
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:20 pm -
1 stop6h 05m
Thu 12/102:41 pm -
1 stop7h 52m
Deal found 10/28![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/305:55 pm -
Nonstop2h 10m
Mon 12/79:21 pm -
Nonstop1h 38m
Deal found 10/26![United Airlines logo]()
$327
This United deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:00 am -
Nonstop3h 00m
Mon 11/233:50 pm -
Nonstop2h 15m
Deal found 10/28![Multiple Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/162:35 pm -
1 stop8h 24m
Wed 12/26:00 am -
1 stop8h 35m
Deal found 10/26![Alaska Airlines logo]()
$450
This Air Canada deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 3/49:20 am -
Nonstop4h 15m
Mon 3/83:40 pm -
Nonstop4h 41m
Deal found 10/25![Air Canada logo]()
$415
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated October 30, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/910:30 am -
Nonstop2h 05m
Mon 11/306:20 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$265
This Porter Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/94:35 pm -
Nonstop2h 05m
Sat 11/2812:15 pm -
Nonstop1h 45m
Deal found 10/26![Porter Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:44 pm -
1 stop5h 17m
Sat 11/147:03 am -
Nonstop1h 44m
Deal found 10/28![United Airlines logo]()
$247
This Kissandfly.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:44 pm -
1 stop5h 17m
Sun 11/157:03 am -
Nonstop1h 44m
Deal found 10/30![Lufthansa logo]()
$234
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:30 pm -
Nonstop2h 13m
Mon 11/168:40 pm -
Nonstop1h 43m
Deal found 10/26![Air Canada logo]()
$228
This Air Canada deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:00 am -
1 stop7h 02m
Tue 11/2412:50 pm -
Nonstop1h 43m
Deal found 10/27![Air Canada logo]()
$238
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:00 am -
1 stop5h 50m
Tue 11/246:41 am -
1 stop7h 27m
Deal found 10/27![American Airlines logo]()
$254
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:16 pm -
Nonstop2h 20m
Mon 11/238:07 am -
Nonstop1h 52m
Deal found 10/27![American Airlines logo]()
$256
This Air Canada deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/194:30 pm -
Nonstop2h 13m
Sun 11/228:45 am -
Nonstop1h 42m
Deal found 10/26![Air Canada logo]()
$257
This SmartFares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Fri 11/208:00 am -
1 stop8h 00m
Tue 11/2410:15 am -
Nonstop1h 37m
Deal found 10/26![Air Canada logo]()
$222
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:21 pm -
Nonstop2h 20m
Wed 11/254:50 pm -
1 stop5h 57m
Deal found 10/27![American Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:09 am -
Nonstop2h 30m
Sun 11/298:45 pm -
Nonstop2h 14m
Deal found 10/27![American Airlines logo]()
$255
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 30, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Trip.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/168:50 am -
1 stop14h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$135
This eDestinos deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2210:29 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Porter Airlines logo]()
$135
This Jetabroad deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/244:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Porter Airlines logo]()
$136
This Gotogate deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/269:50 am -
1 stop6h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Air Canada logo]()
$137
This Gotogate deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/268:05 am -
2 stops7h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Air Canada logo]()
$139
This Trip.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/174:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Porter Airlines logo]()
$139
This Trip.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2110:29 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Porter Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:45 am -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$141
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/164:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Porter Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/110:35 am -
Nonstop1h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Porter Airlines logo]()
$142
This SmartFares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Wed 12/94:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Air Transat logo]()
$145
This Gotogate deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Fri 11/274:30 pm -
Nonstop2h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Air Canada logo]()
$147
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Kiwi.com) |
One-way from | $135 (Trip.com) |
Popular in | October |
Cheapest in | February |
Average price | $316 |
Good round-trip deal | $274 or less |
Good one-way deal | $243 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 30, 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
Tue 11/24
2:20 pm-8:17 pm
1 stop6h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
Quickest round-trip
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Fri 12/25
10:30 am-11:35 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Sat 11/21
10:30 am-11:35 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Thu 12/10
4:35 pm-5:40 pm
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Fri 11/20
4:35 pm-5:40 pm
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Thu 11/19
10:30 am-11:35 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Thu 12/24
10:30 am-11:35 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Tue 11/24
10:29 am-11:34 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$176
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Mon 11/23
1:37 pm-5:10 pm
Nonstop3h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$180
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Tue 3/9
8:45 am-10:20 pm
2 stops13h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$180
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
YYC-ORD
YUL-ORD
YEG-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
YYC-ORD
YUL-ORD
What is the cheapest month to book a flight from Canada to Chicago?
Currently, February is the cheapest month in which you can book a flight from Canada to Chicago (average of $293). Flying from Canada to Chicago in October is currently the most expensive (average of $379). 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 30, 2026.
A simple way to save on the total cost of your ticket is to fly from Canada to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 7% on your trip compared to booking a flight in the evening.
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. Tuesday 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 30, 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
Comfort
8.0
Overall
8.0
Boarding
8.2
Food
7.6
Entertainment
6.9
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.2
Food
7.6
Entertainment
6.9
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.2
Food
7.6
Entertainment
6.9
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.2
Food
7.6
Entertainment
6.9
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.2
Food
7.6
Entertainment
6.9
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.2
Food
7.6
Entertainment
6.9
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 30, 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 30, 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$510 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$533 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$163 | Average$342 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$185 | Average$375 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$193 | Average$415 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$318 | FlexibilityNo cancel fee | On-timeN/A |