$62+ Cheap flights from Chicago (CHI) to Canada
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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Mar 1 — Mar 81
1 adult, Economy
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Find cheap flights from Chicago to Canada with Cheapflights
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Cheapest flights from Chicago to CanadaExplore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2026.
Explore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2026.
This Trip.com deal was found by Cheapflights users on 1/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Mon 5/116:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/29![WestJet logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Mon 4/2712:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 1/26![WestJet logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Sun 5/312:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 1/29![WestJet logo]()
$168
This FlightHub deal was found by Cheapflights users on 1/29. 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.
Mon 5/45:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Thu 5/76:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/29![WestJet logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Mon 5/1112:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 1/28![WestJet logo]()
$169
This FlightHub deal was found by Cheapflights users on 1/29. 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 5/225:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Wed 5/276:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/29![WestJet logo]()
$173
This FlightHub deal was found by Cheapflights users on 1/29. 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 5/295:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Sat 6/612:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 1/29![WestJet logo]()
$181
This FlightHub deal was found by Cheapflights users on 1/29. 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.
Thu 5/75:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Mon 5/116:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/29![WestJet logo]()
$181
This Booking.com deal was found by Cheapflights users on 1/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:30 pm
ORD
- YYC
Nonstop3h 55m
Multiple Airlines
Sat 5/96:30 am
YYC
- ORD
1 stop7h 25m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Fri 3/69:00 am
YYC
- ORD
Nonstop3h 35m
WestJet
Deal found 1/29![WestJet logo]()
$183
This FlightHub deal was found by Cheapflights users on 1/29. 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.
Thu 4/305:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Sun 5/36:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/29![WestJet logo]()
$183
This Booking.com deal was found by Cheapflights users on 1/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:55 am
ORD
- YYC
1 stop9h 48m
Air Canada
Sat 5/96:30 am
YYC
- ORD
1 stop9h 29m
Air Canada
Deal found 1/29![Air Canada logo]()
$184
Best flights from Chicago to CanadaDiscover carefully curated flight deals from Chicago to Canada that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 30, 2026.
Discover carefully curated flight deals from Chicago to Canada that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 30, 2026.
This FlightHub deal was found by Cheapflights users on 1/29. 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.
Sun 4/265:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Thu 4/306:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/29![WestJet logo]()
$188
This deal was found by Cheapflights users on 1/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/108:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/29![Porter Airlines logo]()
$192
This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1112:45 pm
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sun 4/129:15 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$196
This Mytrip deal was found by Cheapflights users on 1/29. 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.
Thu 2/198:00 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Mon 2/238:15 am
YYZ
- ORD
Nonstop1h 58m
Air Canada
Deal found 1/29![Air Canada logo]()
$196
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:00 pm
ORD
- YUL
Nonstop2h 17m
United Airlines
Thu 2/194:45 pm
YUL
- ORD
Nonstop3h 00m
United Airlines
Deal found 1/27![United Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 1/28. 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 3/126:00 am
MDW
- YUL
1 stop10h 31m
Delta
Sun 3/156:00 am
YUL
- MDW
1 stop7h 29m
Delta
Deal found 1/28![Delta logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 1/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
ORD
- YVR
1 stop20h 12m
Alaska Airlines
Sat 5/27:55 am
YVR
- ORD
1 stop9h 57m
Alaska Airlines
Deal found 1/27![Alaska Airlines logo]()
$387
This FlightHub deal was found by Cheapflights users on 1/28. 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 5/2910:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/318:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/28![Porter Airlines logo]()
$197
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:05 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sun 3/12:30 pm
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$197
This Booking.com deal was found by Cheapflights users on 1/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:15 am
ORD
- YTZ
2 stops9h 55m
Air Canada
Sat 3/217:00 am
YTZ
- ORD
1 stop5h 18m
Air Canada
Deal found 1/28![Air Canada logo]()
$203
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:00 am
ORD
- YYC
1 stop7h 53m
United Airlines
Wed 4/2212:34 pm
YYC
- ORD
Nonstop3h 27m
United Airlines
Deal found 1/27![United Airlines logo]()
$206
This WestJet deal was found by Cheapflights users on 1/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Sun 5/106:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/29![WestJet logo]()
$213
This FlightHub deal was found by Cheapflights users on 1/28. 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.
Thu 5/710:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 5/114:00 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/28![Porter Airlines logo]()
$197
This Trip.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1711:05 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Thu 2/199:20 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$197
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:00 am
ORD
- YYZ
1 stop4h 43m
United Airlines
Tue 3/312:45 pm
YYZ
- ORD
Nonstop2h 03m
United Airlines
Deal found 1/27![United Airlines logo]()
$207
This Air Canada deal was found by Cheapflights users on 1/28. 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.
Mon 6/222:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Wed 6/2412:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 1/28![Air Canada logo]()
$213
This Delta deal was found by Cheapflights users on 1/28. 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 5/81:05 pm
MDW
- YUL
1 stop9h 53m
Delta
Sun 5/107:00 am
YUL
- MDW
1 stop5h 56m
Delta
Deal found 1/28![Delta logo]()
$237
This FlightHub deal was found by Cheapflights users on 1/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:35 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 5/118:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/27![Porter Airlines logo]()
$197
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:05 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sat 2/2111:05 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$200
This oojo deal was found by Cheapflights users on 1/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Thu 5/76:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/28![WestJet logo]()
$222
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Tue 4/288:42 am
ORD
- YYC
Nonstop3h 50m
United Airlines
Wed 4/296:00 am
YYC
- ORD
1 stop14h 20m
United Airlines
Deal found 1/28![United Airlines logo]()
$212
This Air Canada deal was found by Cheapflights users on 1/28. 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 6/187:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Sun 6/217:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
Deal found 1/28![Air Canada logo]()
$213
This Delta deal was found by Cheapflights users on 1/29. 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.
Sun 5/176:00 am
MDW
- YUL
1 stop10h 07m
Delta
Wed 5/207:00 am
YUL
- MDW
1 stop7h 07m
Delta
Deal found 1/29![Delta logo]()
$237
This FlightHub deal was found by Cheapflights users on 1/29. 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.
Thu 4/164:15 pm
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Sun 4/192:30 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/29![Porter Airlines logo]()
$197
This Air Canada deal was found by Cheapflights users on 1/28. 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.
Sat 6/62:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Mon 6/812:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 1/28![Air Canada logo]()
$213
This Delta deal was found by Cheapflights users on 1/29. 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.
Sat 4/252:12 pm
MDW
- YUL
1 stop8h 14m
Delta
Fri 5/17:00 am
YUL
- MDW
1 stop10h 25m
Delta
Deal found 1/29![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1910:35 am
ORD
- YUL
Nonstop2h 25m
United Airlines
Wed 2/259:15 am
YUL
- ORD
1 stop6h 05m
United Airlines
Deal found 1/28![United Airlines logo]()
$219
This FlightHub deal was found by Cheapflights users on 1/28. 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 4/242:20 pm
ORD
- YXX
2 stops30h 59m
WestJet
Mon 4/276:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 1/28![WestJet logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/1111:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Tue 5/128:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/27![Porter Airlines logo]()
$202
This Air Canada deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Tue 6/1612:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 1/27![Air Canada logo]()
$213
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated January 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated January 30, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1711:05 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Thu 2/199:20 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/27![Porter Airlines logo]()
$195
This Trip.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1711:05 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Thu 2/199:20 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$197
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:00 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Mon 2/236:40 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 1/28![Air Canada logo]()
$190
This FlightHub deal was found by Cheapflights users on 1/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:05 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Sat 2/2111:05 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/27![Porter Airlines logo]()
$192
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:05 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sat 2/2111:05 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$200
This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:05 am
MDW
- YTZ
Nonstop1h 42m
Air Transat
Mon 2/239:20 am
YTZ
- MDW
Nonstop1h 50m
Air Transat
Deal found 1/27![Air Transat logo]()
$207
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2011:05 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Mon 2/239:20 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$204
This Jetabroad deal was found by Cheapflights users on 1/28. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2011:05 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Tue 2/249:20 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/28![Porter Airlines logo]()
$206
This FlightHub deal was found by Cheapflights users on 1/28. 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 2/2011:05 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Wed 2/259:20 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$208
This Air Canada deal was found by Cheapflights users on 1/29. 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.
Thu 2/263:35 pm
ORD
- YUL
Nonstop2h 05m
Air Canada
Mon 3/21:10 pm
YUL
- ORD
Nonstop2h 45m
Air Canada
Deal found 1/29![Air Canada logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Fri 3/69:00 am
YYC
- ORD
Nonstop3h 35m
WestJet
Deal found 1/29![WestJet logo]()
$183
This Trip.com deal was found by Cheapflights users on 1/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:50 pm
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sat 3/711:00 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$203
One-way flights from Chicago to CanadaSearch for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated January 30, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated January 30, 2026.
This Trip.com deal was found by Cheapflights users on 1/28. 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.
Wed 2/1811:05 am
MDW
- YUL
1 stop4h 25m
Porter Airlines
Deal found 1/28![Porter Airlines logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 1/29![WestJet logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 1/26![WestJet logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 1/29![WestJet logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 1/29![WestJet logo]()
$66
This Super.com deal was found by Cheapflights users on 1/29. 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.
Sun 5/35:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 1/29![WestJet logo]()
$68
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:00 am
MDW
- YUL
1 stop6h 45m
Porter Airlines
Deal found 1/28![Porter Airlines logo]()
$69
This Kissandfly.com deal was found by Cheapflights users on 1/28. 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 4/94:15 pm
MDW
- YUL
1 stop5h 30m
Porter Airlines
Deal found 1/28![Porter Airlines logo]()
$71
This FlightHub deal was found by Cheapflights users on 1/28. 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.
Wed 4/14:15 pm
MDW
- YUL
1 stop5h 30m
Porter Airlines
Deal found 1/28![Porter Airlines logo]()
$72
This Flightnetwork deal was found by Cheapflights users on 1/29. 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 2/207:15 am
ORD
- YUL
Nonstop2h 05m
Air Canada
Deal found 1/29![Air Canada logo]()
$72
This United Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:42 am
ORD
- YYC
Nonstop3h 50m
United Airlines
Deal found 1/26![United Airlines logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 1/29![WestJet logo]()
$74
Find flight deals from Chicago to Canada
Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated January 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Trip.com) |
One-way from | $62 (Trip.com) |
Popular in | January |
Cheapest in | September |
Average price | $309 |
Good round-trip deal | $206 or less |
Good one-way deal | $89 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Canada 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 January 30, 2026.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.
Fly from
Chicago
Fly to
Canada
Route
Depart
Return
Price
ChicagoAbbotsford
ORD - YXX
ORDYXX
Chicago O'Hare Intl
Sun 4/26
5:30 pm-10:25 pm
1 stop6h 55m
Abbotsford
Thu 4/30
6:00 am-4:40 pm
1 stop8h 40m
$188
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 5/8
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Sun 5/10
8:50 am-9:40 am
Nonstop1h 50m
$192
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Sat 4/11
12:45 pm-3:27 pm
Nonstop1h 42m
Toronto Island
Sun 4/12
9:15 am-10:05 am
Nonstop1h 50m
$196
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 2/19
8:00 am-10:40 am
Nonstop1h 40m
Toronto Pearson Intl
Mon 2/23
8:15 am-9:13 am
Nonstop1h 58m
$196
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 5/29
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Sun 5/31
8:50 am-9:40 am
Nonstop1h 50m
$197
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 2/27
11:05 am-1:47 pm
Nonstop1h 42m
Toronto Island
Sun 3/1
2:30 pm-3:20 pm
Nonstop1h 50m
$197
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 5/7
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Mon 5/11
4:00 pm-4:50 pm
Nonstop1h 50m
$197
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 2/17
11:05 am-1:47 pm
Nonstop1h 42m
Toronto Island
Thu 2/19
9:20 am-10:10 am
Nonstop1h 50m
$197
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 5/8
5:35 pm-8:15 pm
Nonstop1h 40m
Toronto Island
Mon 5/11
8:50 am-9:40 am
Nonstop1h 50m
$197
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 4/16
4:15 pm-6:57 pm
Nonstop1h 42m
Toronto Island
Sun 4/19
2:30 pm-3:20 pm
Nonstop1h 50m
$197
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Canada
Have a flexible travel schedule? Discover the best time to fly to Canada from Chicago with our price prediction graph.
ORD-YXX
ORD-YYC
MDW-YTZ
ORD-YYZ
ORD-YUL
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 Chicago to Canada
CHI-CA0
ORD-YXX
ORD-YYC
MDW-YTZ
ORD-YYZ
What is the cheapest month to book a flight from Chicago to Canada?
Currently, April is the cheapest month in which you can book a flight from Chicago to Canada (average of $78). Flying from Chicago to Canada in August is currently the most expensive (average of $132). 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 CHI to CA?
Find hourly flight availability from Chicago to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 30, 2026.
When flying from Chicago to Canada, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 10% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago to Canada?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Canada. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Monday 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.
Weekly flight availability from Chicago to Canada
Explore weekly flight availability from Chicago to Canada. 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 January 30, 2026.
The most flights from CHI to CA0 are scheduled on a Thursday (63 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 Chicago to Canada delayed?
About 19% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 137 minutes.
What is the most punctual flight time for Chicago to Canada 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?
Tuesday 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 Chicago to Canada flights?
Over the last year, Korean Air have had the lowest number of delays on this route, with just 11% of flights being delayed.
Reviews of airlines servicing Canada
Get insights into the airlines that provide service to Canada. 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 Canada. Reviews last updated January 30, 2026.
Peruse reviews from past customers who have flown with Porter Airlines, United Airlines, and American Airlines from Chicago to Canada to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
7.9
Entertainment
6.9
Boarding
8.2
Food
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentMohameed,Nov 2025
LAS - YYZ
Crew
8.6
Comfort
7.9
Entertainment
6.9
Boarding
8.2
Food
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentMohameed,Nov 2025
LAS - YYZ
Crew
8.6
Comfort
7.9
Entertainment
6.9
Boarding
8.2
Food
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentMohameed,Nov 2025
LAS - YYZ
Crew
8.6
Comfort
7.9
Entertainment
6.9
Boarding
8.2
Food
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentMohameed,Nov 2025
LAS - YYZ
Crew
8.6
Comfort
7.9
Entertainment
6.9
Boarding
8.2
Food
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentMohameed,Nov 2025
LAS - YYZ
Crew
8.6
Comfort
7.9
Entertainment
6.9
Boarding
8.2
Food
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentMohameed,Nov 2025
LAS - YYZ
Related info for your journey
Find useful and relevant information for your journey from Chicago to Canada. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 for Chicago to Canada
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chicago to Canada
Discover the top 7 airlines that operate flights from Chicago to Canada. 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 January 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$71 | Average$429 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$80 | Average$379 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$88 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$109 | Average$351 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$110 | Average$275 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$195 | Average$453 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$705 | FlexibilityNo cancel fee | On-time75% |