$136+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Aug 26 — Sep 21
Round-trip
1 adult, Economy
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Find cheap flights from Canada to Chicago with Cheapflights
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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 July 27, 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 July 27, 2026.
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:00 pm
YYZ
- ORD
1 stop5h 12m
Air Canada
Wed 9/163:45 pm
ORD
- YYZ
Nonstop1h 45m
Air Canada
Deal found 7/26![Air Canada logo]()
$205
This Flightnetwork deal was found by Cheapflights users on 7/24. 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.
Thu 9/178:20 am
YTZ
- ORD
2 stops7h 32m
Air Canada
Tue 9/228:45 am
ORD
- YTZ
1 stop6h 05m
Air Canada
Deal found 7/24![Air Canada logo]()
$205
This Trip.com deal was found by Cheapflights users on 7/23. 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.
Thu 9/38:05 am
YYZ
- ORD
Nonstop1h 55m
Air Canada
Tue 9/88:45 am
ORD
- YYZ
1 stop5h 48m
Air Canada
Deal found 7/23![Air Canada logo]()
$206
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 9/213:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/26![Porter Airlines logo]()
$206
This Kissandfly.com deal was found by Cheapflights users on 7/24. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:15 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Sun 9/272:00 pm
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 7/24![Air Canada logo]()
$206
This Trip.com deal was found by Cheapflights users on 7/25. 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.
Tue 8/258:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 9/911:45 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$207
This Flightnetwork deal was found by Cheapflights users on 7/23. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:20 am
YTZ
- ORD
2 stops10h 45m
Air Canada
Tue 9/88:45 am
ORD
- YTZ
1 stop6h 05m
Air Canada
Deal found 7/23![Air Canada logo]()
$207
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 9/41:00 pm
YYZ
- ORD
Nonstop2h 05m
United Airlines
Sat 9/125:53 pm
ORD
- YYZ
Nonstop1h 51m
United Airlines
Deal found 7/27![United Airlines logo]()
$209
This Air Canada deal was found by Cheapflights users on 7/23. 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 9/510:45 am
YTZ
- ORD
1 stop5h 10m
Air Canada
Sat 9/122:00 pm
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 7/23![Air Canada logo]()
$209
This Air Canada deal was found by Cheapflights users on 7/23. 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 9/56:55 pm
YYZ
- ORD
Nonstop1h 58m
Air Canada
Sat 9/129:55 am
ORD
- YYZ
Nonstop1h 45m
Air Canada
Deal found 7/23![Air Canada logo]()
$210
This Flightnetwork deal was found by Cheapflights users on 7/26. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:35 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Tue 9/158:45 am
ORD
- YTZ
2 stops8h 35m
Air Canada
Deal found 7/26![Air Canada logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/233:15 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/26![Porter Airlines logo]()
$211
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 July 27, 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 July 27, 2026.
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Thu 9/245:15 pm
YYZ
- ORD
Nonstop2h 15m
United Airlines
Sun 9/278:50 am
ORD
- YYZ
Nonstop1h 59m
United Airlines
Deal found 7/25![United Airlines logo]()
$209
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 8/2710:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/22![Porter Airlines logo]()
$213
This United deal was found by Cheapflights users on 7/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am
YYZ
- ORD
Nonstop2h 00m
Multiple Airlines
Sun 9/273:40 pm
ORD
- YYZ
1 stop5h 13m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$218
This oojo deal was found by Cheapflights users on 7/22. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:10 am
YTZ
- MDW
Nonstop1h 50m
Air Transat
Thu 9/103:20 pm
MDW
- YTZ
Nonstop1h 40m
Air Transat
Deal found 7/22![Air Transat logo]()
$218
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:08 pm
YYZ
- MDW
1 stop7h 25m
Delta
Mon 9/219:29 am
MDW
- YYZ
1 stop6h 51m
Delta
Deal found 7/25![Delta logo]()
$262
This Air Canada deal was found by Cheapflights users on 7/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:35 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Mon 8/177:25 am
ORD
- YTZ
Nonstop1h 53m
Air Canada
Deal found 7/22![Air Canada logo]()
$308
This Kissandfly.com deal was found by Cheapflights users on 7/22. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:30 am
YYC
- ORD
Nonstop3h 35m
Lufthansa
Sun 9/67:46 pm
ORD
- YYC
Nonstop3h 51m
Lufthansa
Deal found 7/22![Lufthansa logo]()
$335
This United deal was found by Cheapflights users on 7/24. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:00 pm
YYZ
- ORD
Nonstop2h 05m
Multiple Airlines
Sun 9/2011:05 am
ORD
- YYZ
1 stop6h 48m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$218
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 8/3110:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/26![Porter Airlines logo]()
$224
This United Airlines deal was found by Cheapflights users on 7/23. 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 9/109:00 pm
YYZ
- ORD
Nonstop2h 05m
United Airlines
Sat 9/1212:55 pm
ORD
- YYZ
1 stop5h 07m
United Airlines
Deal found 7/23![United Airlines logo]()
$245
This Porter Airlines deal was found by Cheapflights users on 7/25. 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.
Wed 9/91:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 9/133:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$228
This FlightHub deal was found by Cheapflights users on 7/22. 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 9/46:10 pm
YHM
- ORD
1 stop23h 30m
WestJet
Sun 9/135:30 pm
ORD
- YHM
1 stop22h 45m
WestJet
Deal found 7/22![WestJet logo]()
$502
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 9/58:30 am
YYC
- ORD
Nonstop3h 35m
United Airlines
Sun 9/137:45 pm
ORD
- YYC
Nonstop3h 50m
United Airlines
Deal found 7/25![United Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 7/22. 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.
Tue 8/256:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Thu 8/279:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Deal found 7/22![Delta logo]()
$278
This United deal was found by Cheapflights users on 7/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:30 pm
YYC
- ORD
Nonstop3h 35m
Multiple Airlines
Mon 10/2610:15 am
ORD
- YYC
1 stop7h 39m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 7/22. 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.
Mon 8/246:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Wed 8/269:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Deal found 7/22![Delta logo]()
$278
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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.
Wed 8/121:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sat 8/1510:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/27![Porter Airlines logo]()
$256
This KAYAK deal was found by Cheapflights users on 7/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:35 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Wed 8/2610:50 am
ORD
- YTZ
1 stop7h 06m
Air Canada
Deal found 7/23![Air Canada logo]()
$314
This Delta deal was found by Cheapflights users on 7/24. 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.
Mon 8/246:10 am
YYZ
- ORD
1 stop7h 58m
Delta
Tue 8/255:20 pm
ORD
- YYZ
1 stop4h 43m
Delta
Deal found 7/24![Delta logo]()
$282
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 9/31:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 9/611:45 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/27![Porter Airlines logo]()
$259
This United deal was found by Cheapflights users on 7/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:45 am
YUL
- ORD
Nonstop2h 36m
Multiple Airlines
Wed 9/28:40 am
ORD
- YUL
Nonstop2h 19m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 12/246:00 am
YYC
- ORD
1 stop13h 20m
United Airlines
Sat 1/29:00 am
ORD
- YYC
Nonstop3h 54m
United Airlines
Deal found 7/22![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Mon 8/241:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Deal found 7/25![Delta logo]()
$282
This United deal was found by Cheapflights users on 7/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:43 pm
YYZ
- ORD
1 stop4h 57m
Multiple Airlines
Thu 8/132:15 pm
ORD
- YYZ
Nonstop1h 46m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$292
This Air Canada deal was found by Cheapflights users on 7/24. 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.
Sat 8/812:15 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Tue 8/182:00 pm
ORD
- YTZ
Nonstop1h 53m
Air Canada
Deal found 7/24![Air Canada logo]()
$364
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Tue 8/116:10 am
YUL
- ORD
Nonstop2h 41m
United Airlines
Sat 8/155:56 pm
ORD
- YUL
Nonstop2h 30m
United Airlines
Deal found 7/26![United Airlines logo]()
$309
This FlightHub deal was found by Cheapflights users on 7/22. 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.
Mon 8/171:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/233:15 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/22![Porter Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 7/23. 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.
Fri 8/2112:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Sun 8/239:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Deal found 7/23![Delta logo]()
$282
This United deal was found by Cheapflights users on 7/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 am
YYZ
- ORD
Nonstop2h 00m
Multiple Airlines
Wed 8/262:15 pm
ORD
- YYZ
Nonstop1h 46m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Sat 9/129:45 am
YUL
- ORD
Nonstop2h 36m
United Airlines
Tue 9/155:56 pm
ORD
- YUL
Nonstop2h 30m
United Airlines
Deal found 7/22![United Airlines logo]()
$309
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated July 27, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/2310:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/27![Porter Airlines logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/233:15 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/26![Porter Airlines logo]()
$211
This SmartFares deal was found by Cheapflights users on 7/24. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Fri 8/2810:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/24![Porter Airlines logo]()
$215
This SmartFares deal was found by Cheapflights users on 7/24. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:35 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Fri 8/282:00 pm
ORD
- YTZ
Nonstop1h 53m
Air Canada
Deal found 7/24![Air Canada logo]()
$215
This Super.com deal was found by Cheapflights users on 7/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sat 8/2910:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$217
This iWofly deal was found by Cheapflights users on 7/25. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sat 8/2910:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$219
This Trip.com deal was found by Cheapflights users on 7/25. 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.
Tue 8/258:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 9/911:45 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 8/2710:25 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/22![Porter Airlines logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 8/3010:20 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$212
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:35 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Tue 9/12:00 pm
ORD
- YTZ
Nonstop1h 42m
Air Canada
Deal found 7/26![Air Canada logo]()
$214
This Booking.com deal was found by Cheapflights users on 7/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Mon 8/315:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 7/24![WestJet logo]()
$220
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 9/213:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/26![Porter Airlines logo]()
$206
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 July 27, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
This Mytrip deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:00 pm
YYZ
- ORD
1 stop5h 12m
Air Canada
Deal found 7/24![Air Canada logo]()
$136
This FlightHub deal was found by Cheapflights users on 7/23. 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.
Sat 8/228:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/23![Porter Airlines logo]()
$136
This Aunt Betty deal was found by Cheapflights users on 7/26. 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:20 am
YTZ
- ORD
2 stops10h 52m
Air Canada
Deal found 7/26![Air Canada logo]()
$136
This Mytrip deal was found by Cheapflights users on 7/23. 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.
Sat 9/510:30 am
YYZ
- ORD
1 stop5h 25m
Air Canada
Deal found 7/23![Air Canada logo]()
$137
This Trip.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/27![Porter Airlines logo]()
$137
This Air Canada deal was found by Cheapflights users on 7/23. 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 9/57:45 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Deal found 7/23![Air Canada logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/25![Porter Airlines logo]()
$138
This Mytrip deal was found by Cheapflights users on 7/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:35 pm
YTZ
- ORD
Nonstop2h 06m
Air Canada
Deal found 7/26![Air Canada logo]()
$138
This SmartFares deal was found by Cheapflights users on 7/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:10 am
YYZ
- MDW
1 stop4h 07m
Delta
Deal found 7/25![Delta logo]()
$138
This Booking.com deal was found by Cheapflights users on 7/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/14:00 pm
YYZ
- ORD
1 stop5h 05m
Air Canada
Deal found 7/25![Air Canada logo]()
$139
This Air Canada deal was found by Cheapflights users on 7/26. 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.
Sun 9/66:15 am
YYZ
- ORD
1 stop5h 04m
Air Canada
Deal found 7/26![Air Canada logo]()
$140
This Justfly.com deal was found by Cheapflights users on 7/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/22![Porter Airlines logo]()
$140
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 July 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $205 (Trip.com) |
One-way from | $136 (Mytrip) |
Popular in | May |
Cheapest in | September |
Average price | $283 |
Good round-trip deal | $205 or less |
Good one-way deal | $136 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 July 27, 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
Thu 9/24
5:15 pm-6:30 pm
Nonstop2h 15m
Chicago O'Hare Intl
Sun 9/27
8:50 am-11:49 am
Nonstop1h 59m
$209
Quickest round-trip
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Tue 8/25
8:55 am-9:45 am
Nonstop1h 50m
Chicago Midway
Thu 8/27
10:25 am-1:05 pm
Nonstop1h 40m
$213
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 9/23
7:00 am-8:00 am
Nonstop2h 00m
Chicago O'Hare Intl
Sun 9/27
3:40 pm-9:53 pm
1 stop5h 13m
$218
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 9/3
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Thu 9/10
3:20 pm-6:00 pm
Nonstop1h 40m
$218
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 9/18
9:00 pm-10:05 pm
Nonstop2h 05m
Chicago O'Hare Intl
Sun 9/20
11:05 am-6:53 pm
1 stop6h 48m
$218
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 8/26
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Mon 8/31
10:25 am-1:05 pm
Nonstop1h 40m
$224
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 9/9
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sun 9/13
3:20 pm-6:00 pm
Nonstop1h 40m
$228
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 9/10
9:00 pm-10:05 pm
Nonstop2h 05m
Chicago O'Hare Intl
Sat 9/12
12:55 pm-7:02 pm
1 stop5h 07m
$245
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Sat 9/5
8:30 am-1:05 pm
Nonstop3h 35m
Chicago O'Hare Intl
Sun 9/13
7:45 pm-10:35 pm
Nonstop3h 50m
$251
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 8/12
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sat 8/15
10:20 am-1:00 pm
Nonstop1h 40m
$256
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.
YTZ-MDW
YTZ-ORD
YYZ-ORD
YUL-ORD
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
YTZ-MDW
YTZ-ORD
YYZ-ORD
YUL-ORD
What is the cheapest month to book a flight from Canada to Chicago?
Currently, September is the cheapest month in which you can book a flight from Canada to Chicago (average of $279). Flying from Canada to Chicago in July is currently the most expensive (average of $354). 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 July 27, 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 21% on your trip compared to booking a flight at noon.
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 July 27, 2026.
The most flights from CA0 to CHI are scheduled on a Friday (71 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (60 on average).
How often are flights from Canada to Chicago delayed?
About 14% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 136 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 Sunday 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 9% of flights being delayed.
How far ahead should I book a flight from Canada to Chicago?
Booking 83 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 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 July 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. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 July 27, 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.
Overall
8.0
Boarding
8.2
Entertainment
6.9
Comfort
8.0
Food
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Overall
8.0
Boarding
8.2
Entertainment
6.9
Comfort
8.0
Food
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Overall
8.0
Boarding
8.2
Entertainment
6.9
Comfort
8.0
Food
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Overall
8.0
Boarding
8.2
Entertainment
6.9
Comfort
8.0
Food
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Overall
8.0
Boarding
8.2
Entertainment
6.9
Comfort
8.0
Food
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Overall
8.0
Boarding
8.2
Entertainment
6.9
Comfort
8.0
Food
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
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
Valparaiso
Hammond
Saint Joseph
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 July 27, 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 July 27, 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 July 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$489 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$135 | Average$388 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$163 | Average$330 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$167 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$168 | Average$370 | FlexibilityNo cancel fee | On-time52% |