$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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
May 23 — May 301
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Canada with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Canada
Cheapest
Best
Last-minute
One-way
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 23, 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 23, 2026.
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Sun 5/313:45 pm
YXX
- ORD
1 stop22h 55m
WestJet
Deal found 4/22![WestJet logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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
Wed 6/312:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/21![WestJet logo]()
$211
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:30 pm
ORD
- YXX
1 stop6h 55m
WestJet
Fri 6/56:00 am
YXX
- ORD
1 stop8h 40m
WestJet
Deal found 4/22![WestJet logo]()
$211
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 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 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Mon 6/112:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/22![WestJet logo]()
$214
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.
Thu 7/233:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 7/271:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/22![Porter Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/2010:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 5/278:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/21![Porter Airlines logo]()
$217
This Trip.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 6/98:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/18![Porter Airlines logo]()
$218
This Mytrip deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Tue 5/1910:30 am
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Tue 5/268:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$219
This Mytrip deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Tue 5/53:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Wed 5/68:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 9/93:20 pm
ORD
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 9/161:40 pm
YTZ
- ORD
Nonstop1h 55m
Porter Airlines
Deal found 4/20![Porter Airlines 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
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 23, 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 23, 2026.
This Mytrip deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Tue 5/53:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Wed 5/68:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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.
Thu 6/43:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sun 6/78:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/18![Porter Airlines logo]()
$221
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 6/118:50 am
ORD
- YYZ
Nonstop1h 59m
United Airlines
Mon 6/158:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/23![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/2811:09 am
ORD
- YYZ
1 stop3h 05m
Delta
Sun 5/316:10 am
YYZ
- ORD
1 stop7h 51m
Delta
Deal found 4/21![Delta logo]()
$260
This Cheapflightsfares 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 Cheapflightsfares 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 4/23![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.
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 Trip.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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.
Sun 5/3110:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 6/151:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/18![Porter Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 6/76:30 am
YYZ
- ORD
1 stop6h 01m
Delta
Deal found 4/18![Delta logo]()
$260
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.
Tue 6/29:40 pm
ORD
- YYZ
1 stop11h 24m
United Airlines
Fri 6/55:15 pm
YYZ
- ORD
Nonstop2h 03m
United Airlines
Deal found 4/22![United Airlines logo]()
$245
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 KAYAK deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Sun 5/35:30 pm
ORD
- YXX
1 stop23h 25m
WestJet
Thu 5/76:10 pm
YXX
- ORD
1 stop20h 30m
WestJet
Deal found 4/20![WestJet logo]()
$560
This FlightHub deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/143:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/188:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/19![Porter Airlines logo]()
$233
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/79:25 am
ORD
- YYZ
1 stop6h 56m
Delta
Mon 5/112:20 pm
YYZ
- ORD
1 stop6h 54m
Delta
Deal found 4/20![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/152:58 pm
ORD
- YYZ
Nonstop1h 58m
United Airlines
Tue 5/193:00 pm
YYZ
- ORD
1 stop7h 40m
United Airlines
Deal found 4/19![United Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/79:25 am
ORD
- YYZ
1 stop4h 49m
Delta
Sun 5/102:20 pm
YYZ
- ORD
1 stop6h 54m
Delta
Deal found 4/18![Delta logo]()
$260
This Porter Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 4/21![Porter Airlines logo]()
$252
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 stop3h 08m
Delta
Sun 5/316:10 am
YYZ
- MDW
1 stop3h 33m
Delta
Deal found 4/19![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 9/149:30 am
YYC
- ORD
1 stop12h 11m
United Airlines
Deal found 4/21![United Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/149:22 am
MDW
- YYZ
1 stop3h 08m
Delta
Tue 5/266:10 am
YYZ
- MDW
1 stop7h 32m
Delta
Deal found 4/20![Delta logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Thu 6/253:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Mon 6/291:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/21![Porter Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/139:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Sun 7/198:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/19![United Airlines logo]()
$276
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.
Sat 6/136:35 pm
MDW
- YYZ
1 stop3h 27m
Delta
Sat 6/206:30 am
YYZ
- MDW
1 stop7h 39m
Delta
Deal found 4/22![Delta logo]()
$260
This Porter Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Mon 7/610:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 7/78:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/20![Porter Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 7/47:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Sat 7/117:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/18![United Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/201:59 pm
MDW
- YYZ
1 stop8h 15m
Delta
Fri 5/226:10 am
YYZ
- MDW
1 stop3h 33m
Delta
Deal found 4/21![Delta logo]()
$260
This Porter Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/33:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/48:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/20![Porter Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/235:00 am
ORD
- YYC
1 stop14h 30m
United Airlines
Wed 8/269:30 am
YYC
- ORD
1 stop11h 12m
United Airlines
Deal found 4/20![United Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/269:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Fri 6/512:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Deal found 4/20![Delta logo]()
$260
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:30 pm
ORD
- YXX
2 stops28h 15m
Multiple Airlines
Mon 6/18:30 pm
YXX
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$489
This Porter Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2010:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 6/238:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/18![Porter Airlines logo]()
$280
Last-minute flights from Chicago to CanadaDiscover last-minute flight deals from Chicago to Canada. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Canada. Data last updated April 23, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Tue 5/53:20 pm
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Wed 5/68:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$220
This iWofly deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Thu 5/79:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Tue 5/1212:25 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 4/21![Air Canada logo]()
$224
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 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 5/128:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$224
This oojo deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/123:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Tue 5/198:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/19![Porter Airlines logo]()
$223
This Trip.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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
Porter Airlines
Sun 5/178:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/20![Porter Airlines logo]()
$222
This Mytrip deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Tue 5/1910:30 am
MDW
- YTZ
Nonstop1h 40m
Multiple Airlines
Tue 5/268:55 am
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/2010:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Wed 5/278:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/21![Porter Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/257:44 pm
ORD
- YYC
Nonstop3h 53m
United Airlines
Sat 5/308:30 am
YYC
- ORD
Nonstop3h 37m
United Airlines
Deal found 4/20![United Airlines logo]()
$224
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 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Mon 6/112:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/22![WestJet logo]()
$214
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 4/21. Clicking the “Pick Dates” 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
Wed 6/312:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/21![WestJet logo]()
$211
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 23, 2026.
Search for one-way flight options from Chicago to Canada. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Trip.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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.
Sun 5/310:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/18![Porter Airlines logo]()
$90
This Justfly.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Tue 5/123:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/21![Porter Airlines logo]()
$91
This Air Canada deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/52:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/19![Air Canada logo]()
$91
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 4/19![United Airlines logo]()
$91
This Super.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 7/103:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/18![Porter Airlines logo]()
$92
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Wed 7/223:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/20![Porter Airlines logo]()
$93
This Mytrip deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:40 pm
ORD
- YYC
1 stop8h 47m
Air Canada
Deal found 4/19![Air Canada logo]()
$93
This FlightHub deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 4/18![Porter Airlines 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 6/157:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/22![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 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
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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $208 (Trip.com) |
One-way from | $90 (Trip.com) |
Popular in | April |
Cheapest in | September |
Average price | $310 |
Good round-trip deal | $215 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 23, 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 5/5
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Wed 5/6
8:55 am-9:45 am
Nonstop1h 50m
$220
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 6/4
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Sun 6/7
8:50 am-9:40 am
Nonstop1h 50m
$221
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Wed 7/15
10:25 am-1:05 pm
Nonstop1h 40m
Toronto Island
Mon 7/20
8:50 am-9:40 am
Nonstop1h 50m
$226
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Sun 5/31
10:30 am-1:10 pm
Nonstop1h 40m
Toronto Island
Mon 6/15
1:45 pm-2:35 pm
Nonstop1h 50m
$232
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 7/14
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Sat 7/18
8:50 am-9:40 am
Nonstop1h 50m
$233
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 6/11
8:50 am-11:49 am
Nonstop1h 59m
Toronto Pearson Intl
Mon 6/15
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
Tue 6/2
9:40 pm-10:04 am
1 stop11h 24m
Toronto Pearson Intl
Fri 6/5
5:15 pm-6:18 pm
Nonstop2h 03m
$245
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Fri 5/15
2:58 pm-5:56 pm
Nonstop1h 58m
Toronto Pearson Intl
Tue 5/19
3:00 pm-9:40 pm
1 stop7h 40m
$251
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Thu 6/4
3:20 pm-6:00 pm
Nonstop1h 40m
Toronto Island
Mon 6/8
1:45 pm-2:35 pm
Nonstop1h 50m
$252
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-YXX
ORD-YYC
MDW-YTZ
ORD-YTZ
ORD-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-YXX
ORD-YYC
MDW-YTZ
ORD-YTZ
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 23, 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 4% 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 18, 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 23, 2026.
The most flights from CHI to CA0 are scheduled on a Wednesday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 23, 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.
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.6
Boarding
8.2
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.6
Boarding
8.2
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Top regions
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 23, 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$403 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$75 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$88 | Average$297 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$110 | Average$328 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$174 | Average$351 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$199 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$698 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$381 | Average$385 | FlexibilityNo cancel fee | On-time68% |