$153+ Cheap flights from Ontario to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Oct 29 — Nov 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 September 29, 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 September 29, 2026.
This Kissandfly.com deal was found by Cheapflights users on 9/25. 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.
Sat 10/107:43 pm -
1 stop4h 48m
Sun 10/1110:43 am -
Nonstop1h 59m
Deal found 9/25![Lufthansa logo]()
$233
This Kissandfly.com deal was found by Cheapflights users on 9/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:43 pm -
1 stop4h 48m
Sun 10/187:09 am -
Nonstop1h 45m
Deal found 9/28![Lufthansa logo]()
$240
This Kissandfly.com deal was found by Cheapflights users on 9/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:00 am -
1 stop5h 38m
Thu 11/129:21 pm -
Nonstop1h 38m
Deal found 9/28![Lufthansa logo]()
$243
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:35 am -
Nonstop2h 05m
Tue 11/312:20 pm -
Nonstop1h 46m
Deal found 9/29![Porter Airlines logo]()
$274
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:35 pm -
Nonstop2h 05m
Sun 11/112:20 pm -
Nonstop1h 46m
Deal found 9/28![Porter Airlines logo]()
$275
This Kissandfly.com deal was found by Cheapflights users on 9/26. 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.
Sat 10/36:30 am -
Nonstop2h 06m
Sun 10/49:45 am -
Nonstop1h 50m
Deal found 9/26![British Airways logo]()
$286
This FlightHub deal was found by Cheapflights users on 9/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:35 pm -
Nonstop2h 05m
Sun 11/16:20 pm -
Nonstop1h 46m
Deal found 9/28![Porter Airlines logo]()
$286
This Justfly.com deal was found by Cheapflights users on 9/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:35 am -
Nonstop2h 05m
Sun 11/86:20 pm -
Nonstop1h 46m
Deal found 9/29![Porter Airlines logo]()
$287
This deal was found by Cheapflights users on 9/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:45 pm -
Nonstop1h 50m
Mon 10/511:45 am -
Nonstop1h 40m
Deal found 9/27![Porter Airlines logo]()
$288
This FlightHub deal was found by Cheapflights users on 9/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:35 am -
Nonstop2h 05m
Tue 11/312:20 pm -
Nonstop1h 46m
Deal found 9/29![Porter Airlines logo]()
$288
This deal was found by Cheapflights users on 9/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:10 am -
Nonstop1h 50m
Fri 10/233:20 pm -
Nonstop1h 40m
Deal found 9/26![Porter Airlines logo]()
$289
This FlightHub deal was found by Cheapflights users on 9/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:35 am -
Nonstop2h 05m
Mon 11/26:20 pm -
Nonstop1h 46m
Deal found 9/28![Porter Airlines logo]()
$289
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 September 29, 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 September 29, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/131:45 pm -
Nonstop1h 50m
Tue 10/2011:45 am -
Nonstop1h 40m
Deal found 9/29![Porter Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 9/28. 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 11/256:00 am -
1 stop4h 46m
Sat 11/286:44 pm -
1 stop3h 13m
Deal found 9/28![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/25. 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.
Wed 11/253:35 pm -
Nonstop2h 09m
Mon 11/301:57 pm -
Nonstop1h 50m
Deal found 9/25![United Airlines logo]()
$382
This KAYAK deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Tue 10/136:50 am -
1 stop5h 31m
Thu 10/152:00 pm -
Nonstop1h 48m
Deal found 9/24![Air Canada logo]()
$475
This Mytrip deal was found by Cheapflights users on 9/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:00 am -
1 stop4h 00m
Sat 10/246:21 am -
3 stops17h 04m
Deal found 9/25![Multiple Airlines logo]()
$497
This Porter Airlines deal was found by Cheapflights users on 9/28. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:35 am -
Nonstop2h 05m
Wed 12/912:20 pm -
Nonstop1h 46m
Deal found 9/28![Porter Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 9/28. 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 12/22:25 pm -
1 stop5h 01m
Fri 12/47:05 am -
1 stop5h 30m
Deal found 9/28![Delta logo]()
$346
This Porter Airlines deal was found by Cheapflights users on 9/28. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:35 am -
Nonstop2h 05m
Wed 12/912:20 pm -
Nonstop1h 46m
Deal found 9/28![Porter Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 9/28. 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 12/22:25 pm -
1 stop4h 36m
Mon 12/76:41 pm -
1 stop3h 26m
Deal found 9/28![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Sat 10/247:00 am -
Nonstop2h 00m
Sat 10/316:00 am -
1 stop6h 43m
Deal found 9/26![United Airlines logo]()
$382
This Porter Airlines deal was found by Cheapflights users on 9/28. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/304:35 pm -
Nonstop2h 05m
Sun 12/66:20 pm -
Nonstop1h 46m
Deal found 9/28![Porter Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 10/226:00 am -
1 stop7h 47m
Wed 10/289:29 am -
1 stop6h 50m
Deal found 9/28![Delta logo]()
$347
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:45 pm -
Nonstop2h 06m
Tue 10/139:20 pm -
Nonstop1h 39m
Deal found 9/24![United Airlines logo]()
$383
This Porter Airlines deal was found by Cheapflights users on 9/28. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/610:35 am -
Nonstop2h 05m
Sun 12/66:20 pm -
Nonstop1h 46m
Deal found 9/28![Porter Airlines logo]()
$336
This WestJet deal was found by Cheapflights users on 9/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:10 pm -
1 stop23h 30m
Mon 10/195:30 pm -
1 stop22h 45m
Deal found 9/27![WestJet logo]()
$923
This United Airlines deal was found by Cheapflights users on 9/25. 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.
Sat 10/247:00 am -
Nonstop2h 00m
Wed 10/285:00 am -
1 stop5h 48m
Deal found 9/25![United Airlines logo]()
$383
This KAYAK deal was found by Cheapflights users on 9/27. 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.
Tue 10/1310:20 am -
2 stops10h 52m
Fri 10/162:01 pm -
1 stop6h 29m
Deal found 9/27![Air Canada logo]()
$476
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 10/222:26 pm -
1 stop7h 04m
Sun 10/258:29 am -
1 stop4h 07m
Deal found 9/28![Delta logo]()
$359
This Kissandfly.com deal was found by Cheapflights users on 9/26. 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.
Tue 11/104:35 pm -
Nonstop2h 05m
Tue 11/1712:20 pm -
Nonstop1h 46m
Deal found 9/26![Porter Airlines logo]()
$341
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Sat 10/317:44 pm -
1 stop5h 17m
Tue 11/35:00 am -
1 stop5h 48m
Deal found 9/28![United Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 9/28. 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.
Fri 10/239:40 am -
1 stop7h 52m
Sun 11/15:29 pm -
1 stop4h 27m
Deal found 9/28![Delta logo]()
$360
This Cheapflightsfares deal was found by Cheapflights users on 9/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:10 am -
Nonstop1h 50m
Wed 10/143:20 pm -
Nonstop1h 40m
Deal found 9/25![Porter Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Wed 10/146:55 am -
1 stop8h 40m
Sun 10/183:20 pm -
1 stop25h 32m
Deal found 9/27![Multiple Airlines logo]()
$578
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:40 am -
1 stop4h 19m
Thu 10/221:55 pm -
1 stop8h 01m
Deal found 9/29![Delta logo]()
$368
This Air Canada deal was found by Cheapflights users on 9/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:35 am -
1 stop6h 03m
Thu 11/512:50 pm -
1 stop4h 55m
Deal found 9/28![Air Canada logo]()
$542
This Justfly.com deal was found by Cheapflights users on 9/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:10 am -
Nonstop1h 50m
Wed 10/1411:45 am -
Nonstop1h 40m
Deal found 9/26![Porter Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 9/26. 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.
Fri 10/1612:10 pm -
1 stop7h 19m
Sun 10/185:29 pm -
1 stop4h 27m
Deal found 9/26![Delta logo]()
$373
This Kissandfly.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/1010:10 am -
Nonstop1h 50m
Sun 10/113:20 pm -
Nonstop1h 40m
Deal found 9/24![Porter Airlines logo]()
$356
This Gotogate deal was found by Cheapflights users on 9/27. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:35 am -
1 stop6h 03m
Wed 11/1812:50 pm -
1 stop4h 55m
Deal found 9/27![Air Canada logo]()
$589
This Delta deal was found by Cheapflights users on 9/28. 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 11/49:40 am -
1 stop4h 19m
Wed 11/115:05 pm -
1 stop4h 52m
Deal found 9/28![Delta logo]()
$373
Last-minute flights from Ontario to ChicagoDiscover last-minute flight deals from Ontario to Chicago. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Ontario to Chicago. Data last updated September 29, 2026 and is based on user searches.
This Kissandfly.com deal was found by Cheapflights users on 9/27. 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.
Wed 9/306:30 am -
Nonstop2h 10m
Mon 10/52:15 pm -
Nonstop1h 46m
Deal found 9/27![Air Canada logo]()
$322
This Kissandfly.com deal was found by Cheapflights users on 9/26. 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 10/26:30 am -
Nonstop2h 10m
Mon 10/52:15 pm -
Nonstop1h 46m
Deal found 9/26![Air Canada logo]()
$301
This Kissandfly.com deal was found by Cheapflights users on 9/26. 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.
Sat 10/36:30 am -
Nonstop2h 06m
Sun 10/49:45 am -
Nonstop1h 50m
Deal found 9/26![British Airways logo]()
$286
This Kissandfly.com deal was found by Cheapflights users on 9/26. 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.
Sat 10/36:50 pm -
Nonstop1h 58m
Sun 10/48:40 pm -
Nonstop1h 46m
Deal found 9/26![Air Canada logo]()
$338
This Kissandfly.com deal was found by Cheapflights users on 9/25. 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.
Sat 10/107:43 pm -
1 stop4h 48m
Sun 10/1110:43 am -
Nonstop1h 59m
Deal found 9/25![Lufthansa logo]()
$233
This Delta deal was found by Cheapflights users on 9/28. 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.
Mon 10/126:00 am -
1 stop7h 47m
Tue 10/131:27 pm -
1 stop8h 29m
Deal found 9/28![Delta logo]()
$347
This Delta deal was found by Cheapflights users on 9/28. 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.
Fri 10/162:26 pm -
1 stop4h 34m
Tue 10/209:29 am -
1 stop3h 07m
Deal found 9/28![Delta logo]()
$346
This Kissandfly.com deal was found by Cheapflights users on 9/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:43 pm -
1 stop4h 48m
Sun 10/187:09 am -
Nonstop1h 45m
Deal found 9/28![Lufthansa logo]()
$240
This Air Canada deal was found by Cheapflights users on 9/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:00 pm -
Nonstop1h 55m
Tue 10/278:45 am -
Nonstop1h 42m
Deal found 9/28![Air Canada logo]()
$330
This Delta deal was found by Cheapflights users on 9/28. 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.
Tue 10/209:40 am -
1 stop4h 07m
Tue 10/276:44 pm -
1 stop3h 12m
Deal found 9/28![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 9/28. 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 10/216:00 am -
1 stop7h 59m
Wed 10/281:55 pm -
1 stop8h 01m
Deal found 9/28![Delta logo]()
$334
This Air Canada deal was found by Cheapflights users on 9/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am -
1 stop5h 07m
Tue 11/34:30 pm -
Nonstop1h 40m
Deal found 9/29![Air Canada logo]()
$333
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 September 29, 2026.
Search for one-way flight options from Ontario to Chicago. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This OneTravel deal was found by Cheapflights users on 9/28. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Air Transat logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Porter Airlines logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Porter Airlines logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2810:35 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Porter Airlines logo]()
$168
This Mytrip deal was found by Cheapflights users on 9/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:35 am -
1 stop9h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$170
This Super.com deal was found by Cheapflights users on 9/29. 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.
Mon 11/210:35 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Porter Airlines logo]()
$171
This Mytrip deal was found by Cheapflights users on 9/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:10 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Porter Airlines logo]()
$172
This Flightnetwork deal was found by Cheapflights users on 9/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:35 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Porter Airlines logo]()
$174
This Trip.com deal was found by Cheapflights users on 9/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Porter Airlines logo]()
$176
This Trip.com deal was found by Cheapflights users on 9/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/254:35 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Porter Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 9/25. 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.
Tue 11/249:20 am -
1 stop28h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$177
This FlightHub deal was found by Cheapflights users on 9/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/191:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Porter Airlines logo]()
$177
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 September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Kissandfly.com) |
One-way from | $153 (OneTravel) |
Popular in | October |
Cheapest in | February |
Average price | $263 |
Good round-trip deal | $193 or less |
Good one-way deal | $176 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 7,457,451 searches. Data last updated September 29, 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
Mon 10/19
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$177
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 10/13
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$195
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 11/3
6:00 am-9:32 am
1 stop4h 32m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$196
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 10/24
9:40 am-12:47 pm
1 stop4h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$196
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 12/1
12:15 pm-6:01 pm
1 stop6h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$196
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Wed 10/14
2:26 pm-6:00 pm
1 stop4h 34m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$196
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sat 10/10
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$204
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Wed 10/14
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$207
TorontoChicago
YTZ Toronto Island - ORD Chicago O'Hare Intl
YTZORD
Toronto Island
Wed 10/28
8:30 am-2:52 pm
1 stop7h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$208
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Fri 10/23
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$208
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
YYZ-MDW
YTZ-ORD
YTZ-MDW
YOW-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 Ontario to Chicago
CAON-CHI
YYZ-ORD
YYZ-MDW
YTZ-ORD
YTZ-MDW
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 $257). Flying from Region of Ontario to Chicago in October is currently the most expensive (average of $337). 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 September 29, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 33% on flights from Region of Ontario to Chicago by exploring options for tickets at noon.
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 September 29, 2026.
The most flights from CAON to CHI are scheduled on a Sunday (71 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (52 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 $234 and $400 in October.The cheapest round-trip price found within the last 5 days was $233 on Lufthansa (Oct 10-Oct 11).
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 September 26, 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
Other flight options
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 September 29, 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 September 29, 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 7,457,451 searches. Data last updated September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$495 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$185 | Average$385 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$190 | Average$507 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$193 | Average$303 | FlexibilityNo cancel fee | On-time71% |