$135+ Cheap flights from Canada 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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Find cheap flights from Canada to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Canada to Chicago
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Cheapest flights from Canada to ChicagoExplore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 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 June 16, 2026.
This Air Canada deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:55 pm
YYZ
- ORD
Nonstop1h 57m
Air Canada
Mon 9/79:50 am
ORD
- YYZ
Nonstop1h 45m
Air Canada
Deal found 6/15![Air Canada logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 6/293:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/12![Porter Airlines logo]()
$206
This Kissandfly.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:25 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Sun 8/27:25 am
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 6/11![Air Canada logo]()
$206
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Mon 10/57:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 6/12![United Airlines logo]()
$207
This Mytrip deal was found by Cheapflights users on 6/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 7/510:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/13![Porter Airlines logo]()
$207
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:25 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Mon 7/62:00 pm
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 6/15![Air Canada logo]()
$207
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:15 am
YYZ
- ORD
1 stop5h 02m
Air Canada
Sat 9/265:35 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 6/15![Air Canada logo]()
$208
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/210:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11![Porter Airlines logo]()
$208
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:25 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Sun 8/238:45 am
ORD
- YTZ
1 stop6h 06m
Air Canada
Deal found 6/15![Air Canada logo]()
$208
This Trip.com deal was found by Cheapflights users on 6/14. 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 7/24:00 pm
YYZ
- ORD
Nonstop1h 57m
Air Canada
Sun 7/59:50 am
ORD
- YYZ
Nonstop1h 45m
Air Canada
Deal found 6/14![Air Canada logo]()
$209
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:15 am
YYZ
- ORD
1 stop5h 02m
Air Canada
Sun 9/205:35 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 6/15![Air Canada logo]()
$210
This Porter Airlines deal was found by Cheapflights users on 6/11. 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 7/128:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 7/303:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11![Porter Airlines logo]()
$210
Best flights from Canada to ChicagoDiscover carefully curated flight deals from Canada to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 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 June 16, 2026.
This Mytrip deal was found by Cheapflights users on 6/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 7/510:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/13![Porter Airlines logo]()
$207
This United deal was found by Cheapflights users on 6/11. 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.
Sun 8/237:00 am
YYZ
- ORD
Nonstop2h 00m
Multiple Airlines
Mon 8/242:15 pm
ORD
- YYZ
Nonstop1h 46m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Wed 7/151:00 pm
YYZ
- ORD
Nonstop2h 06m
United Airlines
Sun 7/197:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 6/13![United Airlines logo]()
$219
This Air Canada deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2912:15 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Sun 7/57:25 am
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 6/15![Air Canada logo]()
$237
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:09 pm
YYZ
- MDW
1 stop5h 50m
Delta
Tue 9/85:45 pm
MDW
- YYZ
1 stop4h 14m
Delta
Deal found 6/15![Delta logo]()
$240
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/1610:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/12![Porter Airlines logo]()
$208
This Trip.com deal was found by Cheapflights users on 6/14. 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 7/28:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sat 7/410:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/14![Porter Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Sat 7/187:43 pm
YYZ
- ORD
1 stop4h 48m
United Airlines
Mon 8/179:29 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Deal found 6/13![United Airlines logo]()
$234
This United deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:43 pm
YYZ
- ORD
1 stop4h 48m
Multiple Airlines
Tue 7/143:45 pm
ORD
- YYZ
Nonstop1h 44m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:24 pm
YYZ
- MDW
1 stop5h 09m
Delta
Thu 9/179:30 am
MDW
- YYZ
1 stop6h 50m
Delta
Deal found 6/15![Delta logo]()
$240
This Porter Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 7/101:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Tue 7/283:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11![Porter Airlines logo]()
$210
This United deal was found by Cheapflights users on 6/12. 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.
Fri 8/77:43 pm
YYZ
- ORD
1 stop4h 48m
Multiple Airlines
Sun 8/99:50 am
ORD
- YYZ
Nonstop1h 45m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:15 pm
YYZ
- MDW
1 stop5h 22m
Delta
Sat 10/179:30 am
MDW
- YYZ
1 stop4h 49m
Delta
Deal found 6/12![Delta logo]()
$240
This United Airlines deal was found by Cheapflights users on 6/11. 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 7/317:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Tue 8/42:56 pm
ORD
- YYZ
Nonstop2h 00m
United Airlines
Deal found 6/11![United Airlines logo]()
$247
This Porter Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 7/101:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 7/2910:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11![Porter Airlines logo]()
$210
This United deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:44 am
YYZ
- ORD
1 stop8h 15m
Multiple Airlines
Sat 9/53:40 pm
ORD
- YYZ
1 stop6h 15m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
YYZ
- MDW
1 stop4h 07m
Delta
Sun 9/209:30 am
MDW
- YYZ
1 stop4h 45m
Delta
Deal found 6/15![Delta logo]()
$240
This Delta deal was found by Cheapflights users on 6/11. 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
YYZ
- MDW
1 stop3h 42m
Delta
Sun 9/135:59 pm
MDW
- YYZ
1 stop3h 58m
Delta
Deal found 6/11![Delta logo]()
$240
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Mon 6/297:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 6/12![United Airlines logo]()
$265
This Mytrip deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 8/203:15 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/14![Porter Airlines logo]()
$222
This United deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:00 pm
YYZ
- ORD
Nonstop2h 05m
Multiple Airlines
Mon 7/202:15 pm
ORD
- YYZ
Nonstop1h 46m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$246
This Porter Airlines deal was found by Cheapflights users on 6/13. 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.
Sun 9/131:40 pm
YTZ
- ORD
Nonstop1h 55m
Porter Airlines
Thu 9/1711:45 am
ORD
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/13![Porter Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:10 am
YYZ
- ORD
1 stop7h 53m
Delta
Wed 7/228:52 am
ORD
- YYZ
1 stop7h 32m
Delta
Deal found 6/15![Delta logo]()
$252
This United Airlines deal was found by Cheapflights users on 6/12. 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 8/1612:15 pm
YTZ
- ORD
Nonstop2h 04m
United Airlines
Mon 8/3110:50 am
ORD
- YTZ
1 stop6h 56m
United Airlines
Deal found 6/12![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:09 pm
YYZ
- MDW
1 stop6h 58m
Delta
Wed 7/159:19 am
MDW
- YYZ
1 stop7h 05m
Delta
Deal found 6/12![Delta logo]()
$252
This Porter Airlines deal was found by Cheapflights users on 6/13. 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.
Tue 6/308:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 7/13:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/13![Porter Airlines logo]()
$237
This United deal was found by Cheapflights users on 6/12. 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.
Wed 7/229:45 am
YUL
- ORD
Nonstop2h 35m
Multiple Airlines
Mon 7/2711:05 am
ORD
- YUL
Nonstop2h 18m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:25 pm
YTZ
- ORD
Nonstop2h 04m
United Airlines
Tue 8/411:07 am
ORD
- YTZ
1 stop6h 39m
United Airlines
Deal found 6/13![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:05 am
YYZ
- MDW
1 stop7h 41m
Delta
Mon 7/61:26 pm
MDW
- YYZ
1 stop8h 36m
Delta
Deal found 6/15![Delta logo]()
$252
This Porter Airlines deal was found by Cheapflights users on 6/11. 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.
Mon 7/138:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Fri 7/313:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11![Porter Airlines logo]()
$238
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated June 16, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 6/11. 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 6/252:00 pm
YYZ
- ORD
Nonstop1h 55m
Air Canada
Sun 6/288:40 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Deal found 6/11![Air Canada logo]()
$212
This Booking.com deal was found by Cheapflights users on 6/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 6/2810:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/12![Porter Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Tue 6/3010:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/12![Porter Airlines logo]()
$206
This Air Canada deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/17:25 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Sun 7/57:25 am
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 6/16![Air Canada logo]()
$210
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 7/123:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/14![Porter Airlines logo]()
$211
This Mytrip deal was found by Cheapflights users on 6/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 7/510:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/13![Porter Airlines logo]()
$207
This Trip.com deal was found by Cheapflights users on 6/14. 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 7/24:00 pm
YYZ
- ORD
Nonstop1h 57m
Air Canada
Sun 7/59:50 am
ORD
- YYZ
Nonstop1h 45m
Air Canada
Deal found 6/14![Air Canada logo]()
$209
This Trip.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/29:30 am
YTZ
- ORD
1 stop6h 20m
Air Canada
Sun 7/57:25 am
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 6/13![Air Canada logo]()
$212
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:25 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Mon 7/62:00 pm
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 6/15![Air Canada logo]()
$207
This Porter Airlines deal was found by Cheapflights users on 6/11. 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 7/128:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 7/303:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11![Porter Airlines logo]()
$210
This Kissandfly.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:25 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Sun 8/27:25 am
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 6/11![Air Canada logo]()
$206
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/210:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11![Porter Airlines logo]()
$208
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 June 16, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Flightnetwork deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:00 pm
YYZ
- ORD
Nonstop1h 58m
Air Canada
Deal found 6/15![Air Canada logo]()
$135
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/12![Porter Airlines logo]()
$135
This Air Canada deal was found by Cheapflights users on 6/11. 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.
Mon 8/1012:25 pm
YYZ
- ORD
Nonstop1h 57m
Air Canada
Deal found 6/11![Air Canada logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/15![Porter Airlines logo]()
$136
This Air Canada deal was found by Cheapflights users on 6/14. 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.
Wed 8/1210:45 am
YTZ
- ORD
1 stop4h 59m
Air Canada
Deal found 6/14![Air Canada logo]()
$136
This Mytrip deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/29:00 am
YYZ
- ORD
1 stop6h 50m
Air Canada
Deal found 6/14![Air Canada logo]()
$137
This Mytrip deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:15 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Deal found 6/14![Air Canada logo]()
$137
This Air Canada deal was found by Cheapflights users on 6/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:00 pm
YYZ
- ORD
1 stop5h 12m
Air Canada
Deal found 6/13![Air Canada logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/15![Porter Airlines logo]()
$138
This Flightnetwork deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2012:15 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Deal found 6/15![Air Canada logo]()
$138
This Air Canada deal was found by Cheapflights users on 6/11. 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.
Sat 9/124:00 pm
YYZ
- ORD
1 stop5h 12m
Air Canada
Deal found 6/11![Air Canada logo]()
$139
This Flightnetwork deal was found by Cheapflights users on 6/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:15 pm
YTZ
- ORD
Nonstop2h 04m
Air Canada
Deal found 6/14![Air Canada logo]()
$139
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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Air Canada) |
One-way from | $135 (Flightnetwork) |
Popular in | June |
Cheapest in | September |
Average price | $284 |
Good round-trip deal | $217 or less |
Good one-way deal | $134 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 2,558,603 searches. Data last updated June 16, 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
Quickest round-trip
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 7/2
8:50 am-9:40 am
Nonstop1h 50m
Chicago Midway
Sun 7/5
10:25 am-1:05 pm
Nonstop1h 40m
$207
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 8/14
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sun 8/16
10:20 am-1:00 pm
Nonstop1h 40m
$208
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 7/2
8:50 am-9:40 am
Nonstop1h 50m
Chicago Midway
Sat 7/4
10:25 am-1:05 pm
Nonstop1h 40m
$209
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 7/10
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Tue 7/28
3:20 pm-6:00 pm
Nonstop1h 40m
$210
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 7/10
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 7/29
10:25 am-1:05 pm
Nonstop1h 40m
$210
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 8/23
7:00 am-8:00 am
Nonstop2h 00m
Chicago O'Hare Intl
Mon 8/24
2:15 pm-5:01 pm
Nonstop1h 46m
$219
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 7/15
1:00 pm-2:06 pm
Nonstop2h 06m
Chicago O'Hare Intl
Sun 7/19
7:09 am-9:54 am
Nonstop1h 45m
$219
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 8/12
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Thu 8/20
3:15 pm-5:55 pm
Nonstop1h 40m
$222
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Sun 9/13
1:40 pm-2:35 pm
Nonstop1h 55m
Chicago O'Hare Intl
Thu 9/17
11:45 am-2:25 pm
Nonstop1h 40m
$225
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 7/18
7:43 pm-11:31 pm
1 stop4h 48m
Chicago O'Hare Intl
Mon 8/17
9:29 pm-12:13 am
Nonstop1h 44m
$234
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.
YTZ-MDW
YYZ-ORD
YTZ-ORD
YYZ-MDW
YUL-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
YTZ-MDW
YYZ-ORD
YTZ-ORD
YYZ-MDW
What is the cheapest month to book a flight from Canada to Chicago?
Currently, April is the cheapest month in which you can book a flight from Canada to Chicago (average of $255). Flying from Canada to Chicago in June is currently the most expensive (average of $363). 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 June 16, 2026.
A simple way to save on the total cost of your ticket is to fly from Canada to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.
Weekly flight availability from Canada to Chicago
Explore weekly flight availability from Canada to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 16, 2026.
The most flights from CA0 to CHI are scheduled on a Tuesday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).
How often are flights from Canada to Chicago delayed?
About 13% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 136 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 Sunday 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 8% of flights being delayed.
How far ahead should I book a flight from Canada to Chicago?
Booking 83 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 June 13, 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. Sunday at noon 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 June 16, 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
Food
7.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodJustin,May 2026
YYZ - MCO
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodJustin,May 2026
YYZ - MCO
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodJustin,May 2026
YYZ - MCO
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodJustin,May 2026
YYZ - MCO
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodJustin,May 2026
YYZ - MCO
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodJustin,May 2026
YYZ - MCO
Related info for your journey
Find useful and relevant information for your journey from Canada to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
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 June 16, 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 June 16, 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 2,558,603 searches. Data last updated June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$446 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$119 | Average$412 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$138 | Average$314 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$163 | Average$370 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$167 | Average$379 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$241 | Average$288 | FlexibilityNo cancel fee | On-timeN/A |