$106+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
May 17 — May 241
Round-trip
1 adult, Economy
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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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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 17, 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 17, 2026.
This Justfly.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Sun 5/315:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/14![WestJet logo]()
$175
This FlightHub deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:30 am
YUL
- MDW
1 stop4h 10m
Porter Airlines
Sun 6/710:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$181
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Sun 5/318:55 pm
ORD
- YYC
Nonstop3h 48m
American Airlines
Deal found 4/15![American Airlines logo]()
$189
This Booking.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:30 am
YUL
- MDW
1 stop4h 15m
Porter Airlines
Fri 5/293:20 pm
MDW
- YUL
1 stop3h 50m
Porter Airlines
Deal found 4/16![Porter Airlines logo]()
$190
This Justfly.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:30 am
YUL
- MDW
1 stop9h 05m
Porter Airlines
Fri 6/510:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Sun 5/315:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/14![WestJet logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Fri 5/295:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/14![WestJet logo]()
$197
This SmartFares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:45 pm
YTZ
- MDW
Nonstop1h 50m
Air Transat
Sun 5/1010:30 am
MDW
- YTZ
Nonstop1h 40m
Air Transat
Deal found 4/13![Air Transat logo]()
$204
This Air Canada deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:25 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Sun 5/319:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Deal found 4/15![Air Canada logo]()
$205
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Fri 6/58:50 pm
ORD
- YYC
Nonstop3h 52m
American Airlines
Deal found 4/14![American Airlines logo]()
$205
This Trip.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 5/2010:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$205
This FlightHub deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:05 am
YTZ
- ORD
Nonstop1h 55m
Porter Airlines
Sun 9/1311:45 am
ORD
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/12![Porter Airlines logo]()
$205
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 17, 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 17, 2026.
This Trip.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com 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 4/16![Porter Airlines logo]()
$206
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Sun 6/216:30 am
ORD
- YYZ
1 stop6h 49m
United Airlines
Deal found 4/16![United Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:11 pm
YYZ
- ORD
1 stop3h 41m
Delta
Fri 5/87:00 am
ORD
- YYZ
1 stop5h 30m
Delta
Deal found 4/14![Delta logo]()
$230
This Air Canada deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/910:50 am
YTZ
- ORD
1 stop5h 05m
Air Canada
Sun 7/128:45 am
ORD
- YTZ
1 stop6h 06m
Air Canada
Deal found 4/12![Air Canada logo]()
$414
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 5/610:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$208
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:25 pm
YOW
- ORD
2 stops29h 50m
Multiple Airlines
Mon 5/187:33 pm
ORD
- YOW
2 stops15h 42m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:04 pm
YYZ
- MDW
1 stop3h 29m
Delta
Wed 5/139:22 am
MDW
- YYZ
1 stop3h 08m
Delta
Deal found 4/14![Delta logo]()
$230
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 7/203:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/16![Porter Airlines logo]()
$210
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:00 pm
YYZ
- ORD
Nonstop2h 06m
United Airlines
Sun 5/319:15 pm
ORD
- YYZ
Nonstop1h 44m
United Airlines
Deal found 4/16![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/114:04 pm
YYZ
- MDW
1 stop3h 29m
Delta
Wed 5/139:22 am
MDW
- YYZ
1 stop3h 08m
Delta
Deal found 4/14![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:15 pm
YYZ
- ORD
Nonstop2h 03m
United Airlines
Wed 6/177:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 4/13![United Airlines logo]()
$237
This Trip.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 5/1010:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$216
This Porter Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Mon 5/1110:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:00 pm
YYZ
- ORD
1 stop7h 40m
United Airlines
Thu 5/141:01 pm
ORD
- YYZ
Nonstop1h 45m
United Airlines
Deal found 4/16![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/29:45 am
YYZ
- ORD
1 stop7h 45m
Delta
Sun 7/58:36 am
ORD
- YYZ
1 stop8h 58m
Delta
Deal found 4/14![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:49 am
YYZ
- ORD
1 stop7h 40m
Delta
Sun 5/317:00 am
ORD
- YYZ
1 stop7h 14m
Delta
Deal found 4/16![Delta logo]()
$239
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Tue 5/53:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 6/95:00 am
ORD
- YYZ
1 stop5h 43m
United Airlines
Deal found 4/12![United Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:20 pm
YYZ
- MDW
1 stop5h 13m
Delta
Sun 5/109:22 am
MDW
- YYZ
1 stop3h 08m
Delta
Deal found 4/15![Delta logo]()
$240
This Porter Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Tue 5/123:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:10 am
YYZ
- MDW
1 stop3h 33m
Delta
Sun 5/319:22 am
MDW
- YYZ
1 stop3h 08m
Delta
Deal found 4/15![Delta logo]()
$240
This Porter Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Sun 5/3110:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$224
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1812:15 pm
YTZ
- ORD
Nonstop1h 55m
United Airlines
Sun 6/217:25 am
ORD
- YTZ
Nonstop1h 41m
United Airlines
Deal found 4/16![United Airlines logo]()
$279
This Air Canada deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:35 pm
YTZ
- ORD
1 stop4h 23m
Air Canada
Tue 5/128:45 am
ORD
- YTZ
1 stop6h 07m
Air Canada
Deal found 4/16![Air Canada logo]()
$429
This Porter Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Thu 5/73:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:45 am
YYC
- ORD
1 stop10h 05m
Delta
Tue 5/122:11 pm
ORD
- YYC
1 stop9h 46m
Delta
Deal found 4/16![Delta logo]()
$253
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:30 am
YYC
- ORD
Nonstop3h 37m
United Airlines
Fri 5/297:42 pm
ORD
- YYC
Nonstop3h 55m
United Airlines
Deal found 4/16![United Airlines logo]()
$293
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Tue 5/510:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 am
YYC
- ORD
1 stop9h 13m
Delta
Sat 9/2612:15 pm
ORD
- YYC
1 stop9h 29m
Delta
Deal found 4/16![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/224:55 pm
YUL
- ORD
Nonstop2h 49m
United Airlines
Wed 5/276:04 pm
ORD
- YUL
Nonstop2h 22m
United Airlines
Deal found 4/15![United Airlines logo]()
$296
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated April 17, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:45 pm
YTZ
- MDW
Nonstop1h 50m
Air Transat
Sun 5/1010:30 am
MDW
- YTZ
Nonstop1h 40m
Air Transat
Deal found 4/13![Air Transat logo]()
$204
This Air Canada deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:25 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Mon 5/115:35 pm
ORD
- YYZ
Nonstop1h 42m
Air Canada
Deal found 4/15![Air Canada logo]()
$206
This Trip.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Wed 5/2010:30 am
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/15![Porter Airlines logo]()
$205
This Justfly.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:30 am
YUL
- MDW
1 stop9h 05m
Porter Airlines
Fri 6/510:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 4/13![Porter Airlines logo]()
$194
This Booking.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:30 am
YUL
- MDW
1 stop4h 15m
Porter Airlines
Fri 5/293:20 pm
MDW
- YUL
1 stop3h 50m
Porter Airlines
Deal found 4/16![Porter Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Sun 5/315:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/14![WestJet logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Fri 5/295:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/14![WestJet logo]()
$197
This Air Canada deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:25 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Sun 5/319:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Deal found 4/15![Air Canada logo]()
$205
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Sun 5/318:55 pm
ORD
- YYC
Nonstop3h 48m
American Airlines
Deal found 4/15![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Fri 6/58:50 pm
ORD
- YYC
Nonstop3h 52m
American Airlines
Deal found 4/14![American Airlines logo]()
$205
This Justfly.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Sun 5/315:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 4/14![WestJet logo]()
$175
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Sun 6/78:50 pm
ORD
- YYC
Nonstop3h 52m
American Airlines
Deal found 4/16![American 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 April 17, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/14![WestJet logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 4/13![WestJet logo]()
$107
This Mytrip deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:30 am
YUL
- MDW
1 stop4h 15m
Porter Airlines
Deal found 4/12![Porter Airlines logo]()
$114
This Trip.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:35 am
YUL
- MDW
1 stop5h 00m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$115
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Deal found 4/14![American Airlines logo]()
$120
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:30 am
YYC
- ORD
Nonstop3h 37m
United Airlines
Deal found 4/15![United Airlines logo]()
$121
This iWofly deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:55 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 4/16![Air Canada logo]()
$124
This Justfly.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com 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 4/13![Porter Airlines logo]()
$124
This Mytrip deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:05 am
YTZ
- ORD
Nonstop1h 55m
Porter Airlines
Deal found 4/16![Porter Airlines logo]()
$124
This Trip.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:50 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$125
This Trip.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/81:45 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/16![Porter Airlines logo]()
$126
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:55 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/14![Porter Airlines logo]()
$127
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 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $175 (Justfly.com) |
One-way from | $106 (Kiwi.com) |
Popular in | April |
Cheapest in | July |
Average price | $317 |
Good round-trip deal | $183 or less |
Good one-way deal | $96 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 17, 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
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
$206
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 5/1
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 5/6
10:30 am-1:10 pm
Nonstop1h 40m
$208
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 7/16
8:50 am-9:40 am
Nonstop1h 50m
Chicago Midway
Mon 7/20
3:20 pm-6:00 pm
Nonstop1h 40m
$210
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/18
7:00 am-8:00 am
Nonstop2h 00m
Chicago O'Hare Intl
Sun 6/21
6:30 am-2:19 pm
1 stop6h 49m
$215
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 5/1
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sun 5/10
10:30 am-1:10 pm
Nonstop1h 40m
$216
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Tue 5/5
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Mon 5/11
10:30 am-1:10 pm
Nonstop1h 40m
$217
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 5/1
8:55 am-9:45 am
Nonstop1h 50m
Chicago Midway
Tue 5/5
3:20 pm-6:00 pm
Nonstop1h 40m
$221
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 5/9
8:55 am-9:45 am
Nonstop1h 50m
Chicago Midway
Tue 5/12
3:20 pm-6:00 pm
Nonstop1h 40m
$224
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 5/29
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sun 5/31
10:30 am-1:10 pm
Nonstop1h 40m
$224
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 5/7
8:55 am-9:45 am
Nonstop1h 50m
Chicago Midway
Thu 5/7
3:20 pm-6:00 pm
Nonstop1h 40m
$229
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.
YYC-ORD
YTZ-MDW
YTZ-ORD
YOW-ORD
YYZ-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
YYC-ORD
YTZ-MDW
YTZ-ORD
YOW-ORD
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 17, 2026.
A simple way to save on the total cost of your ticket is to fly from Canada to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 22% 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 11, 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 17, 2026.
The most flights from CA0 to CHI are scheduled on a Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 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 138 minutes.
What is the most punctual flight time for Canada to Chicago flights?
Historically, flights departing at night 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 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 17, 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.
Crew
8.6
Food
7.6
Entertainment
7.0
Overall
8.0
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Crew
8.6
Food
7.6
Entertainment
7.0
Overall
8.0
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Crew
8.6
Food
7.6
Entertainment
7.0
Overall
8.0
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Crew
8.6
Food
7.6
Entertainment
7.0
Overall
8.0
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Crew
8.6
Food
7.6
Entertainment
7.0
Overall
8.0
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Crew
8.6
Food
7.6
Entertainment
7.0
Overall
8.0
Boarding
8.2
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.
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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 17, 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 17, 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$333 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$90 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$101 | Average$397 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$137 | Average$297 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$167 | Average$364 | FlexibilityNo cancel fee | On-time71% |