$90+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
May 3 — May 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Canada with Cheapflights
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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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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 April 3, 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 April 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Sat 5/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/1![WestJet logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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
Thu 4/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 3/30![WestJet logo]()
$214
This FlightHub deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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.
Tue 7/2110:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/258:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/1![Porter Airlines logo]()
$219
This Air Canada deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 6/267:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Mon 6/297:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
Deal found 4/1![Air Canada logo]()
$219
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/18:35 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Mon 5/46:40 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 4/2![Air Canada logo]()
$219
This Vliegwinkel deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Sun 4/262:30 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/31![Porter Airlines logo]()
$221
This Air Canada deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 7/1311:05 am
ORD
- YTZ
1 stop5h 46m
Air Canada
Sat 7/1812:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 3/31![Air Canada logo]()
$221
This Flightnetwork deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Thu 5/149:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Thu 5/216:15 am
YYZ
- ORD
1 stop5h 03m
Air Canada
Deal found 3/30![Air Canada logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2311:00 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sun 4/261:30 pm
YTZ
- MDW
1 stop24h 30m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$222
This Air Canada deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 7/311:05 am
ORD
- YTZ
1 stop5h 46m
Air Canada
Fri 7/107:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
Deal found 3/30![Air Canada logo]()
$222
This Air Canada deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 7/198:40 pm
ORD
- YYZ
Nonstop1h 45m
Air Canada
Sat 7/252:00 pm
YYZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 3/31![Air Canada logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/17:30 am
MDW
- YTZ
1 stop9h 45m
Multiple Airlines
Sun 5/38:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$223
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 April 3, 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 April 3, 2026.
This Air Canada deal was found by Cheapflights users on 3/29. 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.
Fri 7/2411:05 am
ORD
- YTZ
1 stop5h 46m
Air Canada
Mon 7/2712:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 3/29![Air Canada logo]()
$222
This Porter Airlines deal was found by Cheapflights users on 3/29. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Thu 4/309:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/29![Porter Airlines logo]()
$224
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 6/244:37 pm
ORD
- YYZ
Nonstop2h 00m
United Airlines
Sun 6/288:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 3/30![United Airlines logo]()
$231
This Booking.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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.
Wed 5/203:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Mon 5/258:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$240
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:30 pm
ORD
- YYZ
1 stop5h 01m
Delta
Sun 5/174:04 pm
YYZ
- ORD
1 stop5h 10m
Delta
Deal found 3/29![Delta logo]()
$247
This Trip.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 8/225:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Sun 8/306:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 3/31![WestJet logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Mon 4/278:48 pm
ORD
- YVR
1 stop14h 52m
Alaska Airlines
Mon 5/410:30 am
YVR
- ORD
1 stop7h 22m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$425
This Air Canada deal was found by Cheapflights users on 3/29. 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 7/27:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Wed 7/810:50 am
YTZ
- ORD
1 stop5h 05m
Air Canada
Deal found 3/29![Air Canada logo]()
$222
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/287:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Mon 6/18:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/2![United Airlines logo]()
$232
This FlightHub deal was found by Cheapflights users on 3/29. 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.
Tue 6/2310:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 7/18:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/29![Porter Airlines logo]()
$233
This Delta deal was found by Cheapflights users on 3/29. 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.
Fri 5/19:27 am
MDW
- YYZ
1 stop4h 53m
Delta
Sun 5/36:10 am
YYZ
- MDW
1 stop3h 37m
Delta
Deal found 3/29![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/179:20 pm
ORD
- YYZ
Nonstop1h 39m
United Airlines
Sun 4/1911:00 am
YYZ
- ORD
Nonstop2h 03m
United Airlines
Deal found 4/2![United Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/13:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Sun 5/38:25 am
YTZ
- MDW
1 stop5h 35m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 6/103:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Thu 6/111:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/2![Porter Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 3/29. 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.
Fri 7/39:54 am
MDW
- YYZ
1 stop7h 40m
Delta
Fri 7/104:10 pm
YYZ
- MDW
1 stop3h 15m
Delta
Deal found 3/29![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/244:43 pm
ORD
- YYZ
Nonstop1h 54m
United Airlines
Sun 4/267:00 am
YYZ
- ORD
Nonstop2h 03m
United Airlines
Deal found 4/3![United Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/13:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Mon 5/48:25 am
YTZ
- MDW
1 stop5h 35m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$259
This Mytrip deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 9/238:45 am
ORD
- YTZ
1 stop6h 05m
Air Canada
Wed 9/309:30 am
YTZ
- ORD
1 stop11h 42m
Air Canada
Deal found 4/3![Air Canada logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 3/29. 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.
Tue 6/303:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 7/58:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/29![Porter Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/296:36 pm
MDW
- YYZ
1 stop3h 23m
Delta
Mon 6/16:10 am
YYZ
- MDW
1 stop7h 32m
Delta
Deal found 4/2![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/149:04 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Tue 5/191:00 pm
YYZ
- ORD
Nonstop2h 01m
United Airlines
Deal found 4/1![United Airlines logo]()
$232
This KAYAK deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Fri 6/128:20 am
YTZ
- ORD
1 stop4h 51m
Air Canada
Deal found 3/30![Air Canada logo]()
$271
This Super.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2210:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 6/248:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/2![Porter Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/99:22 am
MDW
- YYZ
1 stop3h 08m
Delta
Sun 5/106:10 am
YYZ
- MDW
1 stop3h 33m
Delta
Deal found 4/1![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/305:57 pm
ORD
- YYZ
Nonstop1h 47m
United Airlines
Sun 5/31:00 pm
YYZ
- ORD
Nonstop2h 01m
United Airlines
Deal found 4/3![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 7/89:20 am
MDW
- YYZ
1 stop3h 14m
Delta
Mon 7/1312:09 pm
YYZ
- MDW
1 stop7h 16m
Delta
Deal found 4/2![Delta logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 6/263:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 6/281:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/29![Porter Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 3/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:05 am
ORD
- YYZ
Nonstop1h 44m
United Airlines
Wed 4/291:00 pm
YYZ
- ORD
Nonstop2h 01m
United Airlines
Deal found 3/29![United Airlines logo]()
$233
This Justfly.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Sun 8/306:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 4/3![WestJet logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 5/117:33 pm
ORD
- YTZ
3 stops25h 15m
Multiple Airlines
Tue 10/610:05 am
YTZ
- ORD
Nonstop1h 55m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$325
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated April 3, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/167:55 am
ORD
- YYZ
Nonstop1h 36m
Air Canada
Fri 4/176:15 am
YYZ
- ORD
1 stop5h 38m
Air Canada
Deal found 4/2![Air Canada logo]()
$223
This Porter Airlines deal was found by Cheapflights users on 3/29. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Thu 4/309:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/29![Porter Airlines logo]()
$224
This Vliegwinkel deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Sun 4/262:30 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/31![Porter Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2311:00 am
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Sun 4/261:30 pm
YTZ
- MDW
1 stop24h 30m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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
Thu 4/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 3/30![WestJet logo]()
$214
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/18:35 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Mon 5/46:40 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 4/2![Air Canada logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/17:30 am
MDW
- YTZ
1 stop9h 45m
Multiple Airlines
Sun 5/38:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$223
This Trip.com deal was found by Cheapflights users on 3/29. 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.
Mon 5/43:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Thu 5/148:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/29![Porter Airlines logo]()
$225
This Trip.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/910:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/108:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/1![Porter Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Wed 5/132:50 pm
ORD
- YYZ
Nonstop1h 50m
American Airlines
Sun 5/1711:33 am
YYZ
- ORD
Nonstop2h 10m
American Airlines
Deal found 3/31![American Airlines logo]()
$222
This Flightnetwork deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Thu 5/149:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Thu 5/216:15 am
YYZ
- ORD
1 stop5h 03m
Air Canada
Deal found 3/30![Air Canada logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Sat 5/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/1![WestJet logo]()
$208
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 April 3, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/1![WestJet logo]()
$90
This SmartFares deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:00 am
MDW
- YTZ
Nonstop1h 42m
Air Transat
Deal found 4/2![Air Transat logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 3/30![WestJet logo]()
$93
This Air Canada deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 7/2211:05 am
ORD
- YTZ
1 stop5h 46m
Air Canada
Deal found 4/1![Air Canada logo]()
$93
This Air Canada deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 7/311:05 am
ORD
- YYZ
1 stop6h 00m
Air Canada
Deal found 3/30![Air Canada logo]()
$93
This Mytrip deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:20 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 3/29![WestJet logo]()
$94
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/3011:09 am
ORD
- YYZ
1 stop5h 12m
Delta
Deal found 3/31![Delta logo]()
$94
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/59:23 am
MDW
- YYZ
1 stop8h 08m
Delta
Deal found 3/31![Delta logo]()
$94
This Flysmarter deal was found by Cheapflights users on 3/29. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/28:45 am
ORD
- YTZ
1 stop6h 06m
Air Canada
Deal found 3/29![Air Canada logo]()
$95
This iWofly deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:45 am
ORD
- YTZ
1 stop6h 07m
Air Canada
Deal found 4/1![Air Canada logo]()
$96
This Super.com deal was found by Cheapflights users on 3/29. 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.
Fri 5/293:20 pm
MDW
- YTZ
Nonstop1h 40m
Air Transat
Deal found 3/29![Air Transat logo]()
$97
This Air Canada deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 8/258:45 am
ORD
- YTZ
1 stop6h 06m
Air Canada
Deal found 3/31![Air Canada logo]()
$97
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 April 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $208 (Kiwi.com) |
One-way from | $90 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $280 |
Good round-trip deal | $213 or less |
Good one-way deal | $75 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 April 3, 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
Cheapest round-trip
ChicagoToronto
ORD - YTZ
ORDYTZ
Chicago O'Hare Intl
Fri 7/24
11:05 am-5:51 pm
1 stop5h 46m
Toronto Island
Mon 7/27
12:15 pm-1:10 pm
Nonstop1h 55m
$222
ChicagoToronto
ORD - YTZ
ORDYTZ
Chicago O'Hare Intl
Thu 7/2
7:25 am-10:06 am
Nonstop1h 41m
Toronto Island
Wed 7/8
10:50 am-2:55 pm
1 stop5h 05m
$222
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 4/16
11:00 am-1:42 pm
Nonstop1h 42m
Toronto Island
Thu 4/30
9:25 am-10:15 am
Nonstop1h 50m
$224
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Wed 6/24
4:37 pm-7:37 pm
Nonstop2h 00m
Toronto Pearson Intl
Sun 6/28
8:50 am-9:50 am
Nonstop2h 00m
$231
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 5/28
7:09 am-9:54 am
Nonstop1h 45m
Toronto Pearson Intl
Mon 6/1
8:50 am-9:50 am
Nonstop2h 00m
$232
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Fri 4/17
9:20 pm-11:59 pm
Nonstop1h 39m
Toronto Pearson Intl
Sun 4/19
11:00 am-12:03 pm
Nonstop2h 03m
$232
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Fri 4/24
4:43 pm-7:37 pm
Nonstop1h 54m
Toronto Pearson Intl
Sun 4/26
7:00 am-8:03 am
Nonstop2h 03m
$232
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 5/14
9:04 am-11:49 am
Nonstop1h 45m
Toronto Pearson Intl
Tue 5/19
1:00 pm-2:01 pm
Nonstop2h 01m
$232
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 4/30
5:57 pm-8:44 pm
Nonstop1h 47m
Toronto Pearson Intl
Sun 5/3
1:00 pm-2:01 pm
Nonstop2h 01m
$232
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 6/23
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Wed 7/1
8:50 am-9:40 am
Nonstop1h 50m
$233
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.
ORD-YYC
MDW-YTZ
ORD-YTZ
ORD-YYZ
MDW-YYZ
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-YYC
MDW-YTZ
ORD-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 $83). 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 April 3, 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 12% versus a flight at noon.
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 March 28, 2026.
Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Tuesday at noon 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 April 3, 2026.
The most flights from CHI to CA0 are scheduled on a Friday (67 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (28 on average).
How often are flights from Chicago to Canada delayed?
About 20% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 135 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 April 3, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet 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.
Comfort
8.0
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
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.
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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 April 3, 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 8 airlines flying from Chicago to Canada
Discover the top 8 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 April 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$73 | Average$448 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$74 | Average$392 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$88 | Average$296 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$110 | Average$290 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$172 | Average$316 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$199 | Average$435 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$698 | FlexibilityNo cancel fee | On-time75% |