$125+ Cheap flights from Canada to Chicago (CHI)
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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
May 28 — Jun 41
Round-trip
1 adult, Economy
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Find cheap flights from Canada to Chicago 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
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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 Canada to Chicago
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Cheapest flights from Canada to ChicagoExplore the most affordable flight options available from Canada to Chicago. 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 Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 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.
Wed 5/2012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Wed 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/22![WestJet logo]()
$173
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Tue 5/265:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/26![WestJet logo]()
$175
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.
Thu 5/216:30 am
YYC
- ORD
1 stop7h 25m
Multiple Airlines
Wed 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$195
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Sun 6/78:50 pm
ORD
- YYC
Nonstop3h 52m
American Airlines
Deal found 4/26![American Airlines logo]()
$201
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 6/46:30 am
YUL
- MDW
1 stop9h 05m
Porter Airlines
Sun 6/710:15 am
MDW
- YUL
1 stop6h 00m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$202
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:50 am
YYZ
- ORD
Nonstop2h 00m
Lufthansa
Sun 6/77:09 am
ORD
- YYZ
Nonstop1h 45m
Lufthansa
Deal found 4/27![Lufthansa logo]()
$206
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 5/211:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Tue 5/263:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$206
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.
Wed 6/247:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
Wed 7/12:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 4/27![Air Canada logo]()
$206
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 7/23:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$207
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
YUL
- MDW
1 stop9h 05m
Porter Airlines
Mon 6/110:15 am
MDW
- YUL
1 stop6h 00m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$207
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.
Sat 5/234:00 pm
YYZ
- ORD
1 stop5h 08m
Air Canada
Sat 5/308:35 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 4/27![Air Canada logo]()
$208
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/118:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 7/1310:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$208
Best flights from Canada to ChicagoDiscover carefully curated flight deals from Canada to Chicago 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 Canada to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
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 6/57:43 pm
YYZ
- ORD
1 stop4h 43m
United Airlines
Sun 6/77:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 4/26![United Airlines logo]()
$215
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.
Fri 5/221:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 5/313:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/22![Porter Airlines logo]()
$218
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.
Tue 5/125:05 pm
YYZ
- ORD
1 stop6h 31m
Delta
Thu 5/147:00 am
ORD
- YYZ
1 stop5h 30m
Delta
Deal found 4/25![Delta logo]()
$234
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:55 pm
YTZ
- ORD
1 stop4h 55m
Air Canada
Fri 6/56:30 am
ORD
- YTZ
1 stop11h 12m
Air Canada
Deal found 4/26![Air Canada logo]()
$261
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 6/257:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Mon 6/299:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Deal found 4/27![United Airlines logo]()
$215
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.
Wed 5/278:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Tue 6/210:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/24![Porter Airlines logo]()
$219
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.
Sun 5/246:30 am
YYZ
- MDW
1 stop7h 49m
Delta
Sun 5/319:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Deal found 4/26![Delta logo]()
$234
This Porter 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 5/1310:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$219
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.
Sat 6/611:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Tue 6/97:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 4/24![United Airlines logo]()
$228
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.
Wed 5/274:04 pm
YYZ
- MDW
1 stop3h 29m
Delta
Tue 6/29:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Deal found 4/27![Delta logo]()
$234
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.
Sat 8/158:40 am
YOW
- ORD
1 stop6h 40m
American Airlines
Sun 8/168:09 am
ORD
- YOW
1 stop5h 46m
American Airlines
Deal found 4/27![American Airlines logo]()
$528
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.
Sun 8/28:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 8/510:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/22![Porter Airlines logo]()
$221
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.
Fri 5/227:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Thu 5/281:18 pm
ORD
- YYZ
1 stop9h 36m
United Airlines
Deal found 4/25![United Airlines logo]()
$229
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 5/292:20 pm
YYZ
- MDW
1 stop5h 13m
Delta
Thu 6/49:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Deal found 4/26![Delta logo]()
$234
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 7/107:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Sun 7/129:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Deal found 4/26![United Airlines logo]()
$231
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.
Tue 6/22:20 pm
YYZ
- MDW
1 stop5h 13m
Delta
Fri 6/59:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Deal found 4/24![Delta logo]()
$234
This Porter 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 8/1310:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$249
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.
Tue 6/308:50 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Wed 7/85:55 pm
ORD
- YYZ
Nonstop1h 49m
United Airlines
Deal found 4/27![United Airlines logo]()
$231
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.
Fri 5/222:20 pm
YYZ
- ORD
1 stop4h 45m
Delta
Fri 5/296:00 am
ORD
- YYZ
1 stop6h 40m
Delta
Deal found 4/27![Delta logo]()
$235
This Porter 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 6/110:15 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$252
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.
Wed 7/111:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Wed 7/85:55 pm
ORD
- YYZ
Nonstop1h 49m
United Airlines
Deal found 4/27![United Airlines logo]()
$231
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 6/66:10 am
YYZ
- MDW
1 stop7h 32m
Delta
Sat 6/136:35 pm
MDW
- YYZ
1 stop3h 27m
Delta
Deal found 4/22![Delta logo]()
$235
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 7/308:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/210:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/24![Porter Airlines logo]()
$257
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.
Fri 5/2212:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Sun 5/319:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Deal found 4/22![Delta logo]()
$235
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 5/287:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Tue 6/307:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 4/23![United Airlines logo]()
$243
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.
Wed 9/166:00 am
YYC
- ORD
1 stop14h 12m
United Airlines
Mon 9/217:45 pm
ORD
- YYC
Nonstop3h 51m
United Airlines
Deal found 4/27![United Airlines logo]()
$248
This Porter 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sat 7/410:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/25![Porter Airlines logo]()
$277
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 6/202:24 pm
YYZ
- MDW
1 stop4h 42m
Delta
Tue 6/239:17 am
MDW
- YYZ
1 stop3h 22m
Delta
Deal found 4/24![Delta logo]()
$252
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:10 am
YYZ
- MDW
1 stop7h 26m
Delta
Sun 6/149:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Deal found 4/23![Delta logo]()
$253
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.
Sat 6/67:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Mon 6/85:55 pm
ORD
- YYZ
Nonstop1h 49m
United Airlines
Deal found 4/27![United Airlines logo]()
$259
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated April 28, 2026 and is based on user searches.
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.
Wed 5/2012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Wed 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/22![WestJet logo]()
$173
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Tue 5/265:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/26![WestJet logo]()
$175
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.
Thu 5/216:30 am
YYC
- ORD
1 stop7h 25m
Multiple Airlines
Wed 5/275:30 pm
ORD
- YYC
Nonstop3h 55m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$195
This flygcity.se 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:25 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Mon 5/259:20 pm
ORD
- YYZ
Nonstop1h 39m
Air Canada
Deal found 4/27![Air Canada logo]()
$212
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 5/229:49 am
YYZ
- ORD
1 stop7h 40m
Delta
Thu 5/289:25 am
ORD
- YYZ
1 stop6h 56m
Delta
Deal found 4/25![Delta logo]()
$211
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:00 pm
YYZ
- ORD
1 stop6h 08m
Air Canada
Sat 5/308:35 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 4/26![Air Canada logo]()
$208
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:20 am
YYZ
- ORD
Nonstop2h 12m
American Airlines
Sat 5/3012:33 pm
ORD
- YYZ
1 stop8h 57m
American Airlines
Deal found 4/25![American Airlines logo]()
$209
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.
Sun 5/2412:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Fri 6/125:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/22![WestJet logo]()
$215
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.
Mon 5/2512:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Fri 6/125:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/22![WestJet logo]()
$209
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 5/287:43 pm
YYZ
- ORD
1 stop4h 43m
United Airlines
Mon 6/89:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Deal found 4/27![United Airlines logo]()
$215
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Sun 6/78:50 pm
ORD
- YYC
Nonstop3h 52m
American Airlines
Deal found 4/26![American Airlines logo]()
$201
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
YUL
- MDW
1 stop9h 05m
Porter Airlines
Mon 6/110:15 am
MDW
- YUL
1 stop6h 00m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$207
One-way flights from Canada to ChicagoSearch for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$125
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2310:45 am
YTZ
- ORD
1 stop5h 08m
Air Canada
Deal found 4/23![Air Canada logo]()
$126
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.
Sun 5/2411:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 4/23![United Airlines logo]()
$127
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/78:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$127
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$128
This iWofly 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
Deal found 4/24![Air Canada logo]()
$128
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$129
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 4/24![Air Canada logo]()
$129
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.
Wed 6/38:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/23![Porter Airlines logo]()
$130
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
Deal found 4/23![Air Canada logo]()
$130
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.
Sun 7/128:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$131
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:15 pm
YTZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 4/24![Air Canada logo]()
$131
Find flight deals from Canada to Chicago
Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $175 (FlightHub) |
One-way from | $125 (FlightHub) |
Popular in | April |
Cheapest in | July |
Average price | $317 |
Good round-trip deal | $183 or less |
Good one-way deal | $102 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Canada to Chicago 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 Canada to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 6/5
7:43 pm-11:26 pm
1 stop4h 43m
Chicago O'Hare Intl
Sun 6/7
7:09 am-9:54 am
Nonstop1h 45m
$215
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/25
7:00 am-8:00 am
Nonstop2h 00m
Chicago O'Hare Intl
Mon 6/29
9:15 pm-11:59 pm
Nonstop1h 44m
$215
Quickest round-trip
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 5/22
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sun 5/31
3:20 pm-6:00 pm
Nonstop1h 40m
$218
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 5/27
8:55 am-9:45 am
Nonstop1h 50m
Chicago Midway
Tue 6/2
10:25 am-1:05 pm
Nonstop1h 40m
$219
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Tue 5/12
8:55 am-9:45 am
Nonstop1h 50m
Chicago Midway
Wed 5/13
10:30 am-1:10 pm
Nonstop1h 40m
$219
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sun 8/2
8:50 am-9:40 am
Nonstop1h 50m
Chicago Midway
Wed 8/5
10:25 am-1:05 pm
Nonstop1h 40m
$221
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 6/6
11:00 am-12:00 pm
Nonstop2h 00m
Chicago O'Hare Intl
Tue 6/9
7:09 am-9:54 am
Nonstop1h 45m
$228
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 5/22
7:00 am-8:00 am
Nonstop2h 00m
Chicago O'Hare Intl
Thu 5/28
1:18 pm-11:54 pm
1 stop9h 36m
$229
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 7/10
7:00 am-8:00 am
Nonstop2h 00m
Chicago O'Hare Intl
Sun 7/12
9:15 pm-11:59 pm
Nonstop1h 44m
$231
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 6/30
8:50 am-9:50 am
Nonstop2h 00m
Chicago O'Hare Intl
Wed 7/8
5:55 pm-8:44 pm
Nonstop1h 49m
$231
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Canada to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada with our price prediction graph.
YYZ-ORD
YTZ-MDW
YTZ-ORD
YYZ-MDW
YOW-ORD
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 Canada to Chicago
CA0-CHI
YYZ-ORD
YTZ-MDW
YTZ-ORD
YYZ-MDW
How far ahead should I book a flight from Canada to Chicago?
Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Canada to Chicago. 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 Canada to Chicago?
Currently, November is the cheapest month in which you can book a flight from Canada to Chicago (average of $271). Flying from Canada to Chicago in April is currently the most expensive (average of $373). 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 CA to CHI?
Find hourly flight availability from Canada to Chicago. 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.
A simple way to save on the total cost of your ticket is to fly from Canada to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Canada to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Canada to Chicago. Price data was last updated on April 25, 2026.
Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Thursday mornings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Canada to Chicago
Explore weekly flight availability from Canada to Chicago. 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 CA0 to CHI are scheduled on a Monday (71 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (44 on average).
How often are flights from Canada to Chicago delayed?
About 13% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 137 minutes.
What is the most punctual flight time for Canada to Chicago 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?
Thursday 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 Canada to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 8% of flights being delayed.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 28, 2026.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.6
Entertainment
7.0
Boarding
8.2
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Entertainment
7.0
Boarding
8.2
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Entertainment
7.0
Boarding
8.2
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Entertainment
7.0
Boarding
8.2
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Entertainment
7.0
Boarding
8.2
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Entertainment
7.0
Boarding
8.2
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Related info for your journey
Find useful and relevant information for your journey from Canada to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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
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Alternative routes for Canada to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 28, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Canada to Chicago by cabin class
Find flights from Canada to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Canada and Chicago flights
Browse other Canada and Chicago flight options. Last updated on April 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Canada to Chicago flights
Consider these flights traveling from Canada to Chicago.
Top 5 airlines flying from Canada to Chicago
Discover the top 5 airlines that operate flights from Canada to Chicago. 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$80 | Average$350 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$90 | Average$418 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$101 | Average$404 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$137 | Average$309 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$167 | Average$362 | FlexibilityNo cancel fee | On-time71% |