$56+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Mar 29 — Apr 51
1 adult, Economy
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Find cheap flights from Chicago to Canada with Cheapflights
1. Tell us where you want to go
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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 February 27, 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 February 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 2/23![WestJet logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Tue 5/2612:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/24![WestJet logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Mon 5/255:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Sat 6/612:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/25![WestJet logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Mon 5/255:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Thu 6/412:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/25![WestJet logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Thu 6/412:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/25![WestJet logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Thu 6/1112:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/24![WestJet logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/295:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Mon 6/112:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/23![WestJet logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Fri 5/2212:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/24![WestJet logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 8/65:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Tue 8/1812:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/23![WestJet logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Tue 6/912:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/24![WestJet logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Fri 6/1212:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/24![WestJet logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Sat 8/225:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Sat 8/2912:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 2/25![WestJet logo]()
$163
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 February 27, 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 February 27, 2026.
This FlightHub deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/175:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Sat 5/236:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 2/23![WestJet logo]()
$188
This FlightHub deal was found by Cheapflights users on 2/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/410:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 5/68:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/25![Porter Airlines logo]()
$189
This FlightHub deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:25 am
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Wed 5/138:50 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$213
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Wed 3/2510:35 am
ORD
- YUL
Nonstop2h 25m
United Airlines
Wed 4/14:55 pm
YUL
- ORD
Nonstop2h 52m
United Airlines
Deal found 2/24![United Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 2/26. 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.
Wed 3/2512:00 pm
ORD
- YUL
1 stop5h 35m
Delta
Mon 3/307:00 am
YUL
- ORD
1 stop10h 49m
Delta
Deal found 2/26![Delta logo]()
$237
This Air Canada deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:45 am
ORD
- YTZ
1 stop6h 07m
Air Canada
Tue 5/129:30 am
YTZ
- ORD
1 stop6h 23m
Air Canada
Deal found 2/23![Air Canada logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/310:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 5/98:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/23![Porter Airlines logo]()
$191
This Alaska Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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.
Thu 4/236:00 am
ORD
- YVR
1 stop8h 50m
Alaska Airlines
Thu 4/301:45 pm
YVR
- ORD
1 stop8h 14m
Alaska Airlines
Deal found 2/23![Alaska Airlines logo]()
$397
This Trip.com deal was found by Cheapflights users on 2/26. 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.
Mon 8/105:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Tue 8/186:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 2/26![WestJet logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/53:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 5/118:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/23![Porter Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/57:13 am
ORD
- YUL
Nonstop2h 27m
United Airlines
Thu 4/99:45 am
YUL
- ORD
Nonstop2h 52m
United Airlines
Deal found 2/23![United Airlines logo]()
$214
This Mytrip deal was found by Cheapflights users on 2/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/412:55 pm
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Tue 4/79:25 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 2/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:30 pm
ORD
- YUL
1 stop10h 11m
Delta
Wed 6/106:00 am
YUL
- ORD
1 stop4h 24m
Delta
Deal found 2/25![Delta logo]()
$238
This Air Canada deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/78:45 am
ORD
- YTZ
1 stop6h 07m
Air Canada
Tue 5/129:30 am
YTZ
- ORD
1 stop6h 23m
Air Canada
Deal found 2/23![Air Canada logo]()
$244
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Mon 6/2911:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 2/25![United Airlines logo]()
$222
This Porter Airlines deal was found by Cheapflights users on 2/24. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:55 pm
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Tue 4/289:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/24![Porter Airlines logo]()
$213
This Delta deal was found by Cheapflights users on 2/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:00 pm
ORD
- YUL
1 stop8h 13m
Delta
Fri 6/127:00 am
YUL
- ORD
1 stop10h 44m
Delta
Deal found 2/25![Delta logo]()
$238
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/314:37 pm
ORD
- YYZ
Nonstop2h 00m
United Airlines
Tue 8/411:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 2/25![United Airlines logo]()
$222
This Gotogate deal was found by Cheapflights users on 2/24. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1811:00 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sat 3/2111:00 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$254
This FlightHub deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/13:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 5/48:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/23![Porter Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 2/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/187:10 am
ORD
- YYZ
1 stop6h 58m
Delta
Sat 3/213:59 pm
YYZ
- ORD
1 stop5h 18m
Delta
Deal found 2/24![Delta logo]()
$248
This United Airlines deal was found by Cheapflights users on 2/25. 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 8/51:18 pm
ORD
- YYZ
1 stop9h 36m
United Airlines
Sat 8/811:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 2/25![United Airlines logo]()
$232
This Air Canada deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/110:37 am
ORD
- YTZ
1 stop6h 45m
Air Canada
Sat 4/412:25 pm
YTZ
- ORD
1 stop7h 28m
Air Canada
Deal found 2/26![Air Canada logo]()
$299
This Delta deal was found by Cheapflights users on 2/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:45 am
ORD
- YYZ
1 stop6h 04m
Delta
Wed 4/13:59 pm
YYZ
- ORD
1 stop3h 35m
Delta
Deal found 2/24![Delta logo]()
$248
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Sun 6/146:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 2/25![WestJet logo]()
$309
This Trip.com deal was found by Cheapflights users on 2/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1611:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Thu 3/199:15 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/24![Porter Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/99:20 pm
ORD
- YYZ
Nonstop1h 39m
United Airlines
Sun 5/1010:15 am
YYZ
- ORD
Nonstop2h 03m
United Airlines
Deal found 2/23![United Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Sat 5/912:53 pm
ORD
- YTZ
2 stops24h 55m
Multiple Airlines
Wed 5/138:35 pm
YTZ
- ORD
1 stop16h 07m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$291
This Air Canada deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/31:55 pm
ORD
- YTZ
1 stop6h 37m
Air Canada
Sun 4/57:50 am
YTZ
- ORD
1 stop5h 27m
Air Canada
Deal found 2/26![Air Canada logo]()
$299
This Delta deal was found by Cheapflights users on 2/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:35 am
MDW
- YYZ
1 stop6h 42m
Delta
Sat 3/216:20 am
YYZ
- MDW
1 stop3h 33m
Delta
Deal found 2/24![Delta logo]()
$248
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated February 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated February 27, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 2/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/143:55 pm
ORD
- YYZ
Nonstop1h 39m
Air Canada
Mon 3/3012:05 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 2/25![Air Canada logo]()
$199
This Booking.com deal was found by Cheapflights users on 2/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:00 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Fri 3/202:15 pm
YYZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 2/24![Air Canada logo]()
$200
This Air Canada deal was found by Cheapflights users on 2/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:50 pm
ORD
- YUL
Nonstop2h 07m
Air Canada
Sat 3/289:25 am
YUL
- ORD
Nonstop2h 53m
Air Canada
Deal found 2/24![Air Canada logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2511:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Mon 3/309:15 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/24![Porter Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/2511:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Wed 4/19:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/23![Porter Airlines logo]()
$194
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2511:00 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Mon 3/309:15 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$198
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2611:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Mon 3/309:15 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/25![Porter Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Thu 3/2611:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Sun 3/292:30 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/26![Porter Airlines logo]()
$179
This Trip.com deal was found by Cheapflights users on 2/26. 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.
Thu 3/2611:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Sun 4/59:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/26![Porter Airlines logo]()
$180
This Mytrip deal was found by Cheapflights users on 2/25. 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 3/268:40 pm
ORD
- YYZ
Nonstop1h 39m
Air Canada
Mon 3/3012:05 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 2/25![Air Canada logo]()
$190
This Mytrip deal was found by Cheapflights users on 2/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2611:00 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sun 3/292:30 pm
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$199
This Booking.com deal was found by Cheapflights users on 2/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/298:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Sat 4/112:15 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 2/24![Air Canada logo]()
$212
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 February 27, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated February 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/202:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/23![WestJet logo]()
$56
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Thu 5/145:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/25![WestJet logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/32:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/24![WestJet logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/24![WestJet logo]()
$61
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/24![WestJet logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/24![WestJet logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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.
Sat 8/15:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/23![WestJet logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 7/315:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 2/26![WestJet logo]()
$66
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/218:42 am
ORD
- YYC
Nonstop3h 50m
United Airlines
Deal found 2/23![United Airlines logo]()
$70
This Mytrip deal was found by Cheapflights users on 2/25. 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.
Sun 3/293:45 pm
ORD
- YUL
Nonstop2h 10m
Air Canada
Deal found 2/25![Air Canada logo]()
$72
This United Airlines deal was found by Cheapflights users on 2/26. 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 8/257:45 pm
ORD
- YYC
Nonstop3h 51m
United Airlines
Deal found 2/26![United Airlines logo]()
$75
This American Airlines deal was found by Cheapflights users on 2/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:18 am
ORD
- YUL
Nonstop2h 26m
American Airlines
Deal found 2/25![American Airlines logo]()
$75
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 February 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $151 (Kiwi.com) |
One-way from | $56 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $299 |
Good round-trip deal | $175 or less |
Good one-way deal | $99 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 February 27, 2026.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoAbbotsford
ORD - YXX
ORDYXX
Chicago O'Hare Intl
Sun 5/17
5:30 pm-10:25 pm
1 stop6h 55m
Abbotsford
Sat 5/23
6:00 am-4:40 pm
1 stop8h 40m
$188
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Mon 5/4
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Wed 5/6
8:50 am-9:40 am
Nonstop1h 50m
$189
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Sun 5/3
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Sat 5/9
8:50 am-9:40 am
Nonstop1h 50m
$191
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 5/5
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Mon 5/11
8:50 am-9:40 am
Nonstop1h 50m
$192
ChicagoAbbotsford
ORD - YXX
ORDYXX
Chicago O'Hare Intl
Mon 8/10
5:30 pm-10:25 pm
1 stop6h 55m
Abbotsford
Tue 8/18
6:00 am-4:40 pm
1 stop8h 40m
$207
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Sat 5/9
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Wed 5/13
8:50 am-9:40 am
Nonstop1h 50m
$213
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Sat 4/25
12:55 pm-3:37 pm
Nonstop1h 42m
Toronto Island
Tue 4/28
9:25 am-10:15 am
Nonstop1h 50m
$213
ChicagoMontreal
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Wed 3/25
10:35 am-2:00 pm
Nonstop2h 25m
Montreal Pierre Elliott Trudeau Intl
Wed 4/1
4:55 pm-6:47 pm
Nonstop2h 52m
$214
ChicagoMontreal
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Sun 4/5
7:13 am-10:40 am
Nonstop2h 27m
Montreal Pierre Elliott Trudeau Intl
Thu 4/9
9:45 am-11:37 am
Nonstop2h 52m
$214
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 5/1
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Mon 5/4
8:50 am-9:40 am
Nonstop1h 50m
$218
Showing 1-10 of 60 resultsSorted by cheapest first
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.
MDW-YTZ
ORD-YYZ
ORD-YUL
ORD-YYC
ORD-YXX
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
MDW-YTZ
ORD-YYZ
ORD-YUL
ORD-YYC
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 $77). Flying from Chicago to Canada in August is currently the most expensive (average of $135). 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 February 27, 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 in the morning, which can drop the price by up to 11% 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 February 21, 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. Saturday evenings 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 February 27, 2026.
The most flights from CHI to CA0 are scheduled on a Wednesday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (50 on average).
How often are flights from Chicago to Canada delayed?
About 21% 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, United Airlines have had the lowest number of delays on this route, with just 17% 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 February 27, 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.
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Feb 2026
YYJ - YYZ
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Feb 2026
YYJ - YYZ
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Feb 2026
YYJ - YYZ
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Feb 2026
YYJ - YYZ
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Feb 2026
YYJ - YYZ
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Feb 2026
YYJ - 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.
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Alternative routes for Chicago to Canada
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Canada by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Canada by cabin class
Find flights from Chicago to Canada, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Canada flights
Browse other Chicago and Canada flight options. Last updated on February 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Canada flights
Consider these flights traveling from Chicago to Canada.
Fly to Canada regions
Consider these flights traveling to Canada regions.
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 February 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$436 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$80 | Average$378 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$88 | Average$299 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$110 | Average$306 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$172 | Average$380 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$195 | Average$438 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$698 | FlexibilityNo cancel fee | On-time75% |