$132+ Cheap flights from Ontario to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Sep 14 — Sep 211
Round-trip
1 adult, Economy
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Find cheap flights from Ontario 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 Ontario to Chicago
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Cheapest flights from Ontario to ChicagoExplore the most affordable flight options available from Ontario to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
Explore the most affordable flight options available from Ontario to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
This Air Canada deal was found by Cheapflights users on 8/11. 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.
Wed 9/24:00 pm -
1 stop5h 05m
Wed 9/98:40 pm -
Nonstop1h 46m
Deal found 8/11![Air Canada logo]()
$200
This Air Canada deal was found by Cheapflights users on 8/11. 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.
Thu 9/2412:25 pm -
Nonstop1h 58m
Sun 9/273:40 pm -
1 stop5h 13m
Deal found 8/11![Air Canada logo]()
$201
This Air Canada deal was found by Cheapflights users on 8/9. 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:15 am -
1 stop5h 04m
Wed 9/911:05 am -
1 stop5h 28m
Deal found 8/9![Air Canada logo]()
$202
This Justfly.com deal was found by Cheapflights users on 8/10. 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.
Fri 9/111:45 pm -
Nonstop1h 50m
Sun 9/1311:45 am -
Nonstop1h 40m
Deal found 8/10![Porter Airlines logo]()
$202
This deal was found by Cheapflights users on 8/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:35 pm -
Nonstop2h 06m
Mon 9/282:00 pm -
Nonstop1h 42m
Deal found 8/13![Air Canada logo]()
$202
This Trip.com deal was found by Cheapflights users on 8/14. 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 9/102:00 pm -
Nonstop1h 55m
Sun 9/138:40 pm -
Nonstop1h 46m
Deal found 8/14![Air Canada logo]()
$203
This Trip.com deal was found by Cheapflights users on 8/10. 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.
Tue 9/87:35 pm -
Nonstop2h 06m
Tue 9/152:00 pm -
Nonstop1h 42m
Deal found 8/10![Air Canada logo]()
$203
This Trip.com deal was found by Cheapflights users on 8/11. 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.
Thu 9/1012:15 pm -
Nonstop2h 06m
Sun 9/137:25 am -
Nonstop1h 42m
Deal found 8/11![Air Canada logo]()
$204
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/71:45 pm -
Nonstop1h 50m
Thu 9/103:20 pm -
Nonstop1h 40m
Deal found 8/13![Porter Airlines logo]()
$205
This Trip.com deal was found by Cheapflights users on 8/10. 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.
Tue 9/87:35 pm -
Nonstop2h 06m
Wed 9/98:45 am -
1 stop6h 05m
Deal found 8/10![Air Canada logo]()
$205
This Kissandfly.com deal was found by Cheapflights users on 8/13. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:00 pm -
1 stop5h 12m
Mon 9/215:35 pm -
Nonstop1h 43m
Deal found 8/13![Air Canada logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:45 pm -
Nonstop1h 50m
Fri 9/113:20 pm -
Nonstop1h 40m
Deal found 8/13![Porter Airlines logo]()
$206
Best flights from Ontario to ChicagoDiscover carefully curated flight deals from Ontario to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
Discover carefully curated flight deals from Ontario to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
This FlightHub deal was found by Cheapflights users on 8/10. 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.
Thu 9/1010:10 am -
Nonstop1h 50m
Sat 9/1911:45 am -
Nonstop1h 40m
Deal found 8/10![Air Transat logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/11:45 pm -
Nonstop1h 50m
Tue 9/811:45 am -
Nonstop1h 40m
Deal found 8/14![Porter Airlines logo]()
$221
This Air Canada deal was found by Cheapflights users on 8/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:35 pm -
Nonstop2h 06m
Wed 9/167:25 am -
Nonstop1h 42m
Deal found 8/14![Air Canada logo]()
$230
This United deal was found by Cheapflights users on 8/11. 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.
Mon 9/148:00 pm -
1 stop5h 28m
Fri 9/188:40 pm -
Nonstop1h 46m
Deal found 8/11![Multiple Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Sat 9/59:44 am -
1 stop5h 43m
Tue 9/86:30 am -
1 stop6h 49m
Deal found 8/10![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/1012:08 pm -
1 stop5h 05m
Sat 9/192:00 pm -
1 stop7h 59m
Deal found 8/14![Delta logo]()
$245
This Porter Airlines deal was found by Cheapflights users on 8/13. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:45 pm -
Nonstop1h 50m
Sun 9/203:20 pm -
Nonstop1h 40m
Deal found 8/13![Porter Airlines logo]()
$230
This United deal was found by Cheapflights users on 8/14. 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.
Tue 9/88:00 pm -
1 stop5h 28m
Tue 9/1511:05 am -
1 stop6h 48m
Deal found 8/14![Multiple Airlines logo]()
$235
This FlightHub deal was found by Cheapflights users on 8/10. 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.
Fri 9/47:20 am -
1 stop10h 20m
Mon 9/75:30 pm -
1 stop22h 45m
Deal found 8/10![WestJet logo]()
$473
This Porter Airlines deal was found by Cheapflights users on 8/11. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:45 pm -
Nonstop1h 50m
Thu 9/1011:45 am -
Nonstop1h 40m
Deal found 8/11![Porter Airlines logo]()
$230
This United deal was found by Cheapflights users on 8/14. 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.
Fri 9/119:00 pm -
Nonstop2h 05m
Fri 9/188:40 pm -
Nonstop1h 46m
Deal found 8/14![Multiple Airlines logo]()
$240
This Air Canada deal was found by Cheapflights users on 8/10. 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.
Mon 9/78:20 am -
1 stop4h 40m
Mon 9/1412:55 pm -
1 stop4h 56m
Deal found 8/10![Air Canada logo]()
$267
This Delta deal was found by Cheapflights users on 8/12. 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 9/246:00 am -
1 stop4h 07m
Sun 9/279:29 am -
1 stop6h 51m
Deal found 8/12![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 8/11. 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 9/188:50 am -
Nonstop2h 03m
Sun 9/207:09 am -
Nonstop1h 45m
Deal found 8/11![United Airlines logo]()
$273
This Porter Airlines deal was found by Cheapflights users on 8/13. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:10 am -
Nonstop1h 50m
Sat 9/123:20 pm -
Nonstop1h 40m
Deal found 8/13![Porter Airlines logo]()
$230
This United deal was found by Cheapflights users on 8/12. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:00 am -
Nonstop2h 00m
Sun 9/138:40 pm -
Nonstop1h 46m
Deal found 8/12![Multiple Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 8/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am -
1 stop4h 07m
Sun 9/136:40 pm -
1 stop3h 19m
Deal found 8/11![Delta logo]()
$272
This SmartFares deal was found by Cheapflights users on 8/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:10 am -
Nonstop1h 50m
Sat 10/33:20 pm -
Nonstop1h 40m
Deal found 8/12![Porter Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Sat 9/56:10 am -
Nonstop2h 41m
Sat 10/177:11 am -
Nonstop2h 29m
Deal found 8/10![United Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 8/10. 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.
Tue 9/87:00 am -
1 stop10h 37m
Wed 10/216:30 am -
1 stop10h 08m
Deal found 8/10![Delta logo]()
$278
This Air Canada deal was found by Cheapflights users on 8/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:45 am -
1 stop5h 36m
Sun 9/272:00 pm -
1 stop4h 45m
Deal found 8/14![Air Canada logo]()
$325
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Tue 9/89:45 am -
Nonstop2h 36m
Sat 10/177:11 am -
Nonstop2h 29m
Deal found 8/10![United Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 8/10. 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 9/57:00 am -
1 stop9h 44m
Wed 10/211:27 pm -
1 stop8h 58m
Deal found 8/10![Delta logo]()
$278
This Porter Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:10 am -
Nonstop1h 50m
Tue 9/83:20 pm -
Nonstop1h 40m
Deal found 8/14![Porter Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 8/13. 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 9/259:45 am -
Nonstop2h 36m
Mon 9/287:11 am -
Nonstop2h 29m
Deal found 8/13![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 8/10. 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.
Wed 9/212:47 pm -
1 stop5h 12m
Sat 10/171:27 pm -
1 stop8h 58m
Deal found 8/10![Delta logo]()
$278
This United deal was found by Cheapflights users on 8/14. 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.
Thu 9/1012:15 pm -
Nonstop2h 06m
Sun 9/137:25 am -
Nonstop1h 42m
Deal found 8/14![Multiple Airlines logo]()
$310
This Trip.com deal was found by Cheapflights users on 8/14. 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.
Fri 9/41:45 pm -
Nonstop1h 50m
Mon 9/711:45 am -
Nonstop1h 40m
Deal found 8/14![Porter Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Thu 9/1012:15 pm -
Nonstop2h 06m
Sun 9/137:25 am -
Nonstop1h 42m
Deal found 8/10![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 9/96:00 am -
1 stop4h 07m
Thu 9/109:29 am -
1 stop6h 51m
Deal found 8/13![Delta logo]()
$287
Last-minute flights from Ontario to ChicagoDiscover last-minute flight deals from Ontario to Chicago. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Ontario to Chicago. Data last updated August 15, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 8/11. 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.
Wed 9/24:00 pm -
1 stop5h 05m
Wed 9/98:40 pm -
Nonstop1h 46m
Deal found 8/11![Air Canada logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:45 pm -
Nonstop1h 50m
Fri 9/113:20 pm -
Nonstop1h 40m
Deal found 8/13![Porter Airlines logo]()
$206
This Air Canada deal was found by Cheapflights users on 8/9. 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:15 am -
1 stop5h 04m
Wed 9/911:05 am -
1 stop5h 28m
Deal found 8/9![Air Canada logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/71:45 pm -
Nonstop1h 50m
Thu 9/103:20 pm -
Nonstop1h 40m
Deal found 8/13![Porter Airlines logo]()
$205
This Trip.com deal was found by Cheapflights users on 8/10. 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.
Tue 9/87:35 pm -
Nonstop2h 06m
Tue 9/152:00 pm -
Nonstop1h 42m
Deal found 8/10![Air Canada logo]()
$203
This Trip.com deal was found by Cheapflights users on 8/10. 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.
Tue 9/87:35 pm -
Nonstop2h 06m
Wed 9/98:45 am -
1 stop6h 05m
Deal found 8/10![Air Canada logo]()
$205
This Trip.com deal was found by Cheapflights users on 8/14. 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 9/102:00 pm -
Nonstop1h 55m
Sun 9/138:40 pm -
Nonstop1h 46m
Deal found 8/14![Air Canada logo]()
$203
This Trip.com deal was found by Cheapflights users on 8/11. 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.
Thu 9/1012:15 pm -
Nonstop2h 06m
Sun 9/137:25 am -
Nonstop1h 42m
Deal found 8/11![Air Canada logo]()
$204
This Justfly.com deal was found by Cheapflights users on 8/10. 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.
Fri 9/111:45 pm -
Nonstop1h 50m
Sun 9/1311:45 am -
Nonstop1h 40m
Deal found 8/10![Porter Airlines logo]()
$202
This Kissandfly.com deal was found by Cheapflights users on 8/13. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:00 pm -
1 stop5h 12m
Mon 9/215:35 pm -
Nonstop1h 43m
Deal found 8/13![Air Canada logo]()
$206
This Air Canada deal was found by Cheapflights users on 8/11. 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.
Thu 9/2412:25 pm -
Nonstop1h 58m
Sun 9/273:40 pm -
1 stop5h 13m
Deal found 8/11![Air Canada logo]()
$201
This deal was found by Cheapflights users on 8/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:35 pm -
Nonstop2h 06m
Mon 9/282:00 pm -
Nonstop1h 42m
Deal found 8/13![Air Canada logo]()
$202
One-way flights from Ontario to ChicagoSearch for one-way flight options from Ontario to Chicago. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
Search for one-way flight options from Ontario to Chicago. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
This Trip.com deal was found by Cheapflights users on 8/13. 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.
Fri 9/44:00 pm -
1 stop5h 05m
Deal found 8/13![Air Canada logo]()
$132
This Air Canada deal was found by Cheapflights users on 8/12. 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.
Sat 9/510:45 am -
1 stop5h 10m
Deal found 8/12![Air Canada logo]()
$132
This United Airlines deal was found by Cheapflights users on 8/14. 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 9/81:00 pm -
Nonstop2h 05m
Deal found 8/14![United Airlines logo]()
$133
This Air Canada deal was found by Cheapflights users on 8/12. 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.
Sat 9/56:55 pm -
Nonstop1h 58m
Deal found 8/12![Air Canada logo]()
$134
This Air Canada deal was found by Cheapflights users on 8/10. 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.
Mon 8/317:35 pm -
Nonstop2h 06m
Deal found 8/10![Air Canada logo]()
$134
This Jetabroad deal was found by Cheapflights users on 8/12. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/11:45 pm -
Nonstop1h 50m
Deal found 8/12![Air Transat logo]()
$135
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Sun 9/137:00 am -
Nonstop2h 00m
Deal found 8/12![United Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Tue 8/251:45 pm -
Nonstop1h 50m
Deal found 8/11![Porter Airlines logo]()
$137
This Air Canada deal was found by Cheapflights users on 8/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:15 pm -
Nonstop2h 06m
Deal found 8/14![Air Canada logo]()
$137
This Air Canada deal was found by Cheapflights users on 8/10. 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.
Wed 9/24:00 pm -
1 stop5h 05m
Deal found 8/10![Air Canada logo]()
$138
This Air Canada deal was found by Cheapflights users on 8/10. 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.
Sun 8/308:05 am -
Nonstop1h 55m
Deal found 8/10![Air Canada logo]()
$139
This Air Canada deal was found by Cheapflights users on 8/11. 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 9/154:00 pm -
1 stop5h 12m
Deal found 8/11![Air Canada logo]()
$141
Find flight deals from Ontario to Chicago
Keep the following information in mind while searching for Ontario to Chicago flight deals. Data was last updated August 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $200 (Air Canada) |
One-way from | $132 (Trip.com) |
Popular in | July |
Cheapest in | September |
Average price | $278 |
Good round-trip deal | $205 or less |
Good one-way deal | $169 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Ontario 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 2,558,603 searches. Data last updated August 15, 2026.
Use the filters below to find and compare flights from Ontario to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 9/10
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Sat 9/19
11:45 am-2:25 pm
Nonstop1h 40m
$219
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 9/1
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Tue 9/8
11:45 am-2:25 pm
Nonstop1h 40m
$221
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Mon 9/14
7:35 pm-8:41 pm
Nonstop2h 06m
Chicago O'Hare Intl
Wed 9/16
7:25 am-10:07 am
Nonstop1h 42m
$230
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 9/17
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sun 9/20
3:20 pm-6:00 pm
Nonstop1h 40m
$230
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sun 9/6
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Thu 9/10
11:45 am-2:25 pm
Nonstop1h 40m
$230
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sat 9/12
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Sat 9/12
3:20 pm-6:00 pm
Nonstop1h 40m
$230
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Mon 9/14
8:00 pm-12:28 am
1 stop5h 28m
Chicago O'Hare Intl
Fri 9/18
8:40 pm-11:26 pm
Nonstop1h 46m
$235
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Tue 9/8
8:00 pm-12:28 am
1 stop5h 28m
Chicago O'Hare Intl
Tue 9/15
11:05 am-6:53 pm
1 stop6h 48m
$235
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sat 9/26
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Sat 10/3
3:20 pm-6:00 pm
Nonstop1h 40m
$235
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Fri 9/11
9:00 pm-10:05 pm
Nonstop2h 05m
Chicago O'Hare Intl
Fri 9/18
8:40 pm-11:26 pm
Nonstop1h 46m
$240
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Ontario to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Ontario with our price prediction graph.
YYZ-ORD
YTZ-MDW
YTZ-ORD
YOW-ORD
YYZ-MDW
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 Ontario to Chicago
CAON-CHI
YYZ-ORD
YTZ-MDW
YTZ-ORD
YOW-ORD
What is the cheapest month to book a flight from Region of Ontario to Chicago?
Currently, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $260). Flying from Region of Ontario to Chicago in December is currently the most expensive (average of $319). 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 ON to CHI?
Find hourly flight availability from Ontario 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 August 15, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 36% on flights from Region of Ontario to Chicago by exploring options for tickets in the evening.
Weekly flight availability from Region of Ontario to Chicago
Explore weekly flight availability from Ontario 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 August 15, 2026.
The most flights from CAON to CHI are scheduled on a Friday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).
How much does it cost to fly round-trip from Region of Ontario to Chicago?
Airfare is below average for this route at the moment.
Region of Ontario to Chicago flights typically cost between $256 and $426 in September.The cheapest round-trip price found within the last 5 days was $200 on Air Canada (Sep 2-Sep 9).
How far ahead should I book a flight from Region of Ontario to Chicago?
The best time to book flights from Region of Ontario to Chicago is 87 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Region of Ontario to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Ontario to Chicago. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their Region of Ontario to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Ontario 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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
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Popular flights
Alternative routes for Ontario 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 August 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 Ontario to Chicago by cabin class
Find flights from Ontario to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Ontario and Chicago flights
Browse other Ontario and Chicago flight options. Last updated on August 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Ontario to Chicago
Discover the top 4 airlines that operate flights from Ontario 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 2,558,603 searches. Data last updated August 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$294 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$168 | Average$370 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$189 | Average$301 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$190 | Average$485 | FlexibilityNo cancel fee | On-time69% |