$91+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
May 28 — Jun 41
Round-trip
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 April 28, 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 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 7/1510:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 7/208:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/22![Porter Airlines logo]()
$213
This CAPO Viagens deal was found by Cheapflights users on 4/26. 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 CAPO Viagens is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Sun 8/912:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 4/26![Air Canada logo]()
$213
This Trip.com deal was found by Cheapflights users on 4/27. 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 5/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Mon 5/188:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$214
This Trip.com deal was found by Cheapflights users on 4/25. 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 5/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Tue 5/198:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Sun 5/2410:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Fri 5/291:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 7/313:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Fri 8/71:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$217
This deal was found by Cheapflights users on 4/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:20 pm
ORD
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 9/2810:05 am
YTZ
- ORD
Nonstop1h 55m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$218
This Trip.com deal was found by Cheapflights users on 4/25. 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.
Mon 5/1110:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/178:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/25![Porter Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Tue 7/2110:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/258:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$220
This Mytrip deal was found by Cheapflights users on 4/27. 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 6/112:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Thu 6/1812:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 4/27![Air Canada logo]()
$220
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 5/276:30 am
ORD
- YYZ
1 stop6h 49m
United Airlines
Wed 5/275:15 pm
YYZ
- ORD
Nonstop2h 04m
United Airlines
Deal found 4/23![United Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/810:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 6/168:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$221
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 28, 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 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Tue 7/2110:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/258:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Tue 5/125:57 pm
ORD
- YYZ
Nonstop1h 47m
United Airlines
Sat 5/168:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/25![United Airlines logo]()
$235
This SmartFares deal was found by Cheapflights users on 4/27. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Air Transat
Mon 5/188:55 am
YTZ
- MDW
Nonstop1h 50m
Air Transat
Deal found 4/27![Air Transat logo]()
$243
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
ORD
- YYZ
1 stop6h 40m
Delta
Sat 6/62:30 pm
YYZ
- ORD
1 stop7h 19m
Delta
Deal found 4/27![Delta logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/1310:30 am
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Thu 5/149:15 am
YTZ
- MDW
2 stops50h 49m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:16 am
ORD
- YUL
Nonstop2h 27m
American Airlines
Thu 7/235:29 pm
YUL
- ORD
Nonstop2h 45m
American Airlines
Deal found 4/27![American Airlines logo]()
$365
This Air Canada deal was found by Cheapflights users on 4/27. 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.
Mon 7/202:00 pm
ORD
- YUL
1 stop4h 47m
Air Canada
Thu 7/238:40 am
YUL
- ORD
Nonstop2h 36m
Air Canada
Deal found 4/27![Air Canada logo]()
$370
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 5/2712:55 pm
ORD
- YYZ
Nonstop1h 51m
United Airlines
Sun 5/311:00 pm
YYZ
- ORD
Nonstop2h 06m
United Airlines
Deal found 4/23![United Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/283:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Fri 5/291:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$245
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Fri 5/299:20 pm
ORD
- YYZ
Nonstop1h 39m
United Airlines
Mon 6/18:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/24![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- YYZ
1 stop6h 40m
Delta
Sun 5/3112:09 pm
YYZ
- ORD
1 stop5h 20m
Delta
Deal found 4/26![Delta logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Sat 5/3010:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 6/28:45 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$253
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/102:56 pm
ORD
- YYZ
Nonstop2h 00m
United Airlines
Sun 6/1411:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/22![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 4/26. 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.
Sat 5/165:19 pm
ORD
- YYZ
1 stop4h 40m
Delta
Sun 5/316:10 am
YYZ
- ORD
1 stop7h 51m
Delta
Deal found 4/26![Delta logo]()
$260
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:21 pm
MDW
- YYZ
1 stop8h 41m
Delta
Thu 6/186:05 am
YYZ
- MDW
1 stop4h 09m
Delta
Deal found 4/27![Delta logo]()
$260
This Trip.com deal was found by Cheapflights users on 4/24. 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 6/1510:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 6/168:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/24![Porter Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 6/49:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Sat 6/67:43 pm
YYZ
- ORD
1 stop4h 43m
United Airlines
Deal found 4/27![United Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 5/299:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Sun 5/316:10 am
YYZ
- MDW
1 stop7h 32m
Delta
Deal found 4/25![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 6/49:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Mon 6/87:00 pm
YYZ
- ORD
1 stop5h 30m
United Airlines
Deal found 4/23![United Airlines logo]()
$251
This Porter Airlines deal was found by Cheapflights users on 4/24. 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.
Thu 6/43:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 6/81:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/24![Porter Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 6/199:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Tue 6/2312:09 pm
YYZ
- MDW
1 stop7h 22m
Delta
Deal found 4/25![Delta logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/53:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 6/68:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/22![Porter Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Wed 6/36:10 am
YYZ
- MDW
1 stop7h 32m
Delta
Deal found 4/27![Delta logo]()
$261
This Delta deal was found by Cheapflights users on 4/24. 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.
Thu 5/79:22 am
MDW
- YYZ
1 stop3h 08m
Delta
Mon 5/112:20 pm
YYZ
- MDW
1 stop5h 13m
Delta
Deal found 4/24![Delta logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Tue 6/1610:15 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 6/278:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/181:49 pm
MDW
- YYZ
1 stop8h 25m
Delta
Sun 6/216:10 am
YYZ
- MDW
1 stop7h 26m
Delta
Deal found 4/22![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/511:03 am
ORD
- YTZ
1 stop6h 39m
United Airlines
Fri 6/127:20 pm
YTZ
- ORD
Nonstop1h 56m
United Airlines
Deal found 4/22![United Airlines logo]()
$322
This FlightHub deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/113:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 6/148:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/22![Porter Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 6/136:35 pm
MDW
- YYZ
1 stop3h 27m
Delta
Sat 6/206:10 am
YYZ
- MDW
1 stop4h 04m
Delta
Deal found 4/24![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1311:03 am
ORD
- YTZ
1 stop6h 39m
United Airlines
Sun 6/147:20 pm
YTZ
- ORD
Nonstop1h 56m
United Airlines
Deal found 4/26![United Airlines logo]()
$322
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated April 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/810:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 6/168:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$221
This Trip.com deal was found by Cheapflights users on 4/25. 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.
Mon 5/1110:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/178:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/25![Porter Airlines logo]()
$219
This Trip.com deal was found by Cheapflights users on 4/25. 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 5/1410:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 5/191:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/25![Porter Airlines logo]()
$223
This Trip.com deal was found by Cheapflights users on 4/27. 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 5/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Mon 5/188:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$214
This Trip.com deal was found by Cheapflights users on 4/25. 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 5/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Tue 5/198:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$215
This Trip.com deal was found by Cheapflights users on 4/25. 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 5/1510:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/178:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/25![Porter Airlines logo]()
$222
This Justfly.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Sun 5/248:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Sun 5/2410:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Fri 5/291:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$216
This Trip.com deal was found by Cheapflights users on 4/25. 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.
Mon 5/2510:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 6/11:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/25![Porter Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 5/276:30 am
ORD
- YYZ
1 stop6h 49m
United Airlines
Wed 5/275:15 pm
YYZ
- ORD
Nonstop2h 04m
United Airlines
Deal found 4/23![United Airlines logo]()
$220
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Thu 5/2810:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 5/308:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Fri 5/2912:55 pm
ORD
- YYZ
Nonstop1h 51m
United Airlines
Fri 5/297:43 pm
YYZ
- ORD
1 stop4h 43m
United Airlines
Deal found 4/23![United Airlines logo]()
$226
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 28, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Air Canada deal was found by Cheapflights users on 4/27. 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.
Fri 6/57:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/27![Air Canada logo]()
$91
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Fri 6/59:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Deal found 4/26![United Airlines logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 7/83:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/24![Porter Airlines logo]()
$92
This Mytrip deal was found by Cheapflights users on 4/24. 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.
Fri 7/103:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/24![Porter Airlines logo]()
$93
This Booking.com deal was found by Cheapflights users on 4/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/26![Air Canada logo]()
$94
This Flightnetwork deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 4/22![Air Canada logo]()
$94
This oojo deal was found by Cheapflights users on 4/23. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$95
This Flightnetwork deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/22![Air Canada logo]()
$95
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/113:20 pm
MDW
- YTZ
Nonstop1h 40m
Air Transat
Deal found 4/23![Air Transat logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 7/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$97
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/23![Air Canada logo]()
$97
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/263:45 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Deal found 4/23![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 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Kiwi.com) |
One-way from | $91 (Air Canada) |
Popular in | April |
Cheapest in | September |
Average price | $310 |
Good round-trip deal | $210 or less |
Good one-way deal | $97 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 28, 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
Quickest round-trip
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 7/21
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Sat 7/25
8:50 am-9:40 am
Nonstop1h 50m
$220
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Tue 5/12
5:57 pm-8:44 pm
Nonstop1h 47m
Toronto Pearson Intl
Sat 5/16
8:50 am-9:50 am
Nonstop2h 00m
$235
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Wed 5/27
12:55 pm-3:46 pm
Nonstop1h 51m
Toronto Pearson Intl
Sun 5/31
1:00 pm-2:06 pm
Nonstop2h 06m
$235
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Fri 5/29
9:20 pm-11:59 pm
Nonstop1h 39m
Toronto Pearson Intl
Mon 6/1
8:50 am-9:50 am
Nonstop2h 00m
$235
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Wed 6/10
2:56 pm-5:56 pm
Nonstop2h 00m
Toronto Pearson Intl
Sun 6/14
11:00 am-12:00 pm
Nonstop2h 00m
$235
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 5/15
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Mon 5/18
8:55 am-9:45 am
Nonstop1h 50m
$243
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 5/28
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Fri 5/29
1:45 pm-2:35 pm
Nonstop1h 50m
$245
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 6/4
9:15 pm-11:59 pm
Nonstop1h 44m
Toronto Pearson Intl
Sat 6/6
7:43 pm-11:26 pm
1 stop4h 43m
$251
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 6/4
9:15 pm-11:59 pm
Nonstop1h 44m
Toronto Pearson Intl
Mon 6/8
7:00 pm-11:30 pm
1 stop5h 30m
$251
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Sat 5/30
10:30 am-1:10 pm
Nonstop1h 40m
Toronto Island
Tue 6/2
8:45 am-9:35 am
Nonstop1h 50m
$253
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-YTZ
ORD-YUL
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
MDW-YTZ
ORD-YYZ
ORD-YTZ
ORD-YUL
How far ahead should I book a flight from Chicago to Canada?
Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Canada. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Canada?
Currently, October is the cheapest month in which you can book a flight from Chicago to Canada (average of $236). Flying from Chicago to Canada in December is currently the most expensive (average of $419). 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 28, 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 6% 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 April 25, 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. 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 April 28, 2026.
The most flights from CHI to CA0 are scheduled on a Monday (69 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (35 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 136 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 Friday 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 18% 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 28, 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.
Food
7.6
Boarding
8.2
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.0
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 28, 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 9 airlines flying from Chicago to Canada
Discover the top 9 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 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$71 | Average$412 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$87 | Average$466 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$88 | Average$302 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$324 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$174 | Average$352 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$199 | Average$438 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$328 | Average$698 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$381 | Average$385 | FlexibilityNo cancel fee | On-time68% |