$72+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
May 18 — May 251
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 18, 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 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Fri 6/512:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/14![WestJet logo]()
$210
This FlightHub deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 5/208:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/17![Porter Airlines logo]()
$216
This Mytrip deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:30 am
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Mon 5/111:45 pm
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/108:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$219
This Booking.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/52:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Sun 6/712:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 4/15![Air Canada logo]()
$219
This CAPO Viagens deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CAPO Viagens is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:40 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Thu 9/178:05 am
YYZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 4/16![Air Canada logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Thu 7/238:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/29:35 pm
ORD
- YYZ
1 stop11h 29m
United Airlines
Sun 5/31:00 pm
YYZ
- ORD
Nonstop2h 01m
United Airlines
Deal found 4/17![United Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/13![WestJet logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:45 am
ORD
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 9/2010:05 am
YTZ
- ORD
Nonstop1h 55m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/410:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 6/78:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/188:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/15![Porter 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 18, 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 18, 2026.
This FlightHub deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub 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
Mon 7/208:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$232
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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
Tue 6/28:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/17![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 6/55:19 pm
ORD
- YYZ
1 stop4h 40m
Delta
Sun 6/76:10 am
YYZ
- ORD
1 stop5h 35m
Delta
Deal found 4/17![Delta logo]()
$260
This Air Canada deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 7/172:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Mon 7/2012:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 4/17![Air Canada logo]()
$267
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 6/38:55 pm
ORD
- YYC
Nonstop3h 48m
American Airlines
Mon 6/87:00 am
YYC
- ORD
Nonstop3h 35m
American Airlines
Deal found 4/17![American Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 7/257:55 am
ORD
- YUL
2 stops15h 30m
Multiple Airlines
Thu 7/305:14 pm
YUL
- ORD
1 stop4h 17m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$427
This Justfly.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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.
Sat 7/2510:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Thu 7/308:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/17![Porter Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/286:00 am
ORD
- YYZ
1 stop4h 43m
United Airlines
Wed 6/37:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/17![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/169:36 am
ORD
- YYZ
1 stop7h 23m
Delta
Sat 5/2312:29 pm
YYZ
- ORD
1 stop5h 22m
Delta
Deal found 4/17![Delta logo]()
$260
This Alaska Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- YVR
2 stops11h 29m
Alaska Airlines
Wed 9/211:50 am
YVR
- ORD
2 stops9h 51m
Alaska Airlines
Deal found 4/15![Alaska Airlines logo]()
$528
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/1610:55 am
ORD
- YYZ
Nonstop1h 47m
United Airlines
Sat 5/232:35 pm
YYZ
- ORD
1 stop5h 20m
United Airlines
Deal found 4/17![United Airlines logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares 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
Sun 7/128:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/16![Porter Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:34 pm
ORD
- YYZ
1 stop8h 09m
Delta
Fri 7/109:45 am
YYZ
- ORD
1 stop7h 38m
Delta
Deal found 4/15![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/96:00 am
ORD
- YYZ
1 stop4h 43m
United Airlines
Sun 5/108:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/17![United Airlines logo]()
$253
This Porter Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 7/131:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/12![Porter Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:25 am
ORD
- YYZ
1 stop6h 56m
Delta
Sun 5/3112:29 pm
YYZ
- ORD
1 stop9h 51m
Delta
Deal found 4/16![Delta logo]()
$269
This KAYAK deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:10 am
ORD
- YTZ
1 stop6h 11m
Air Canada
Tue 6/307:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
Deal found 4/15![Air Canada logo]()
$340
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/192:07 pm
ORD
- YYZ
1 stop7h 55m
Delta
Sun 6/216:10 am
YYZ
- ORD
1 stop7h 54m
Delta
Deal found 4/15![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 6/146:30 am
ORD
- YYZ
1 stop6h 49m
United Airlines
Fri 6/197:43 pm
YYZ
- ORD
1 stop4h 43m
United Airlines
Deal found 4/17![United Airlines logo]()
$269
This Porter Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Fri 5/81:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:00 am
ORD
- YYZ
1 stop7h 20m
Delta
Sun 5/104:04 pm
YYZ
- ORD
1 stop5h 10m
Delta
Deal found 4/16![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 9/98:25 pm
ORD
- YYC
Nonstop3h 55m
American Airlines
Sun 9/136:30 am
YYC
- ORD
Nonstop3h 25m
American Airlines
Deal found 4/17![American Airlines logo]()
$404
This Justfly.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 5/258:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/12![Porter Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:45 pm
ORD
- YYC
Nonstop3h 51m
United Airlines
Tue 9/159:30 am
YYC
- ORD
1 stop9h 57m
United Airlines
Deal found 4/13![United Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 7/255:30 pm
ORD
- YVR
1 stop7h 05m
Multiple Airlines
Thu 7/309:30 am
YVR
- ORD
2 stops31h 49m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:25 am
ORD
- YYZ
1 stop3h 05m
Delta
Sat 5/164:10 pm
YYZ
- ORD
1 stop5h 04m
Delta
Deal found 4/15![Delta logo]()
$269
This Porter Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Fri 6/58:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:45 pm
ORD
- YYC
Nonstop3h 51m
United Airlines
Mon 9/146:00 am
YYC
- ORD
1 stop16h 59m
United Airlines
Deal found 4/15![United Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:23 am
MDW
- YYZ
1 stop8h 08m
Delta
Mon 5/186:10 am
YYZ
- MDW
1 stop3h 33m
Delta
Deal found 4/14![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/1611:59 am
MDW
- YVR
1 stop10h 51m
Multiple Airlines
Sat 5/238:25 pm
YVR
- MDW
2 stops12h 47m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$449
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated April 18, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/29:35 pm
ORD
- YYZ
1 stop11h 29m
United Airlines
Sun 5/31:00 pm
YYZ
- ORD
Nonstop2h 01m
United Airlines
Deal found 4/17![United Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Thu 5/71:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Wed 5/68:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$226
This Mytrip deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:30 am
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Mon 5/111:45 pm
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 5/108:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$219
This FlightHub deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 5/208:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/17![Porter Airlines logo]()
$216
This FlightHub deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Thu 5/211:45 pm
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$224
This Booking.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:35 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Thu 5/281:55 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 4/16![Air Canada logo]()
$225
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:42 pm
ORD
- YYC
Nonstop3h 55m
United Airlines
Thu 5/288:30 am
YYC
- ORD
Nonstop3h 37m
United Airlines
Deal found 4/16![United Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/13![WestJet logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Fri 6/512:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/14![WestJet logo]()
$210
This Trip.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Fri 6/58:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$222
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 18, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This eDestinos deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$72
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:30 am
MDW
- YUL
1 stop5h 45m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$73
This FlightHub deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/510:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$90
This Air Canada deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/17![Air Canada logo]()
$91
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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
Deal found 4/17![United Airlines logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/123:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$92
This Super.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/233:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$94
This Air Canada deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/16![Air Canada logo]()
$95
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/141:01 pm
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 4/17![United Airlines logo]()
$95
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/16![Porter Airlines logo]()
$96
This Mytrip deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/13![Porter Airlines 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 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $210 (Kiwi.com) |
One-way from | $72 (eDestinos) |
Popular in | April |
Cheapest in | September |
Average price | $309 |
Good round-trip deal | $214 or less |
Good one-way deal | $106 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 18, 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
Wed 7/15
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Mon 7/20
8:50 am-9:40 am
Nonstop1h 50m
$232
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 5/28
7:09 am-9:54 am
Nonstop1h 45m
Toronto Pearson Intl
Tue 6/2
8:50 am-9:50 am
Nonstop2h 00m
$235
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Sat 7/25
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Thu 7/30
8:50 am-9:40 am
Nonstop1h 50m
$235
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 5/28
6:00 am-11:43 am
1 stop4h 43m
Toronto Pearson Intl
Wed 6/3
7:00 am-8:00 am
Nonstop2h 00m
$245
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Sat 5/16
10:55 am-1:42 pm
Nonstop1h 47m
Toronto Pearson Intl
Sat 5/23
2:35 pm-6:55 pm
1 stop5h 20m
$250
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 7/10
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Sun 7/12
8:50 am-9:40 am
Nonstop1h 50m
$251
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Sat 5/9
6:00 am-11:43 am
1 stop4h 43m
Toronto Pearson Intl
Sun 5/10
8:50 am-9:50 am
Nonstop2h 00m
$253
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 7/9
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Mon 7/13
1:45 pm-2:35 pm
Nonstop1h 50m
$256
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Fri 6/5
5:19 pm-10:59 pm
1 stop4h 40m
Toronto Pearson Intl
Sun 6/7
6:10 am-10:45 am
1 stop5h 35m
$260
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Sat 5/16
9:36 am-5:59 pm
1 stop7h 23m
Toronto Pearson Intl
Sat 5/23
12:29 pm-4:51 pm
1 stop5h 22m
$260
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-YYZ
ORD-YTZ
ORD-YUL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Canada
CHI-CA0
ORD-YYC
MDW-YTZ
ORD-YYZ
ORD-YTZ
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 18, 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 11, 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 18, 2026.
The most flights from CHI to CA0 are scheduled on a Monday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).
How often are flights from Chicago to Canada delayed?
About 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 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 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 18, 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
Overall
8.0
Entertainment
7.0
Food
7.6
Boarding
8.2
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Entertainment
7.0
Food
7.6
Boarding
8.2
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Entertainment
7.0
Food
7.6
Boarding
8.2
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Entertainment
7.0
Food
7.6
Boarding
8.2
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Entertainment
7.0
Food
7.6
Boarding
8.2
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Entertainment
7.0
Food
7.6
Boarding
8.2
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 18, 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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$448 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$74 | Average$399 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$88 | Average$292 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$110 | Average$296 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$174 | Average$342 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$199 | Average$434 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$698 | FlexibilityNo cancel fee | On-time75% |