$115+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
4月 13 — 4月 201
Round-trip
1 adult, Economy
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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 3月 14, 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 3月 14, 2026.
This Mytrip deal was found by Cheapflights users on 3/12. 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.
週五 5/810:35 am
YUL
- MDW
1 stop5h 00m
Porter Airlines
週日 5/1010:25 am
MDW
- YUL
1 stop6h 50m
Porter Airlines
Deal found 3/12![Porter Airlines logo]()
$162
This FlightHub deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週四 4/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
週四 5/75:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 3/10![WestJet logo]()
$186
This FlightHub deal was found by Cheapflights users on 3/13. 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.
週四 5/286:30 am
YUL
- MDW
1 stop4h 10m
Porter Airlines
週日 5/3110:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 3/13![Porter Airlines logo]()
$188
This Trip.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
週五 5/110:35 am
YUL
- MDW
1 stop5h 00m
Porter Airlines
週一 5/43:20 pm
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 3/11![Porter Airlines logo]()
$189
This Trip.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週一 6/14:30 pm
YUL
- ORD
1 stop4h 46m
Air Canada
週日 6/77:25 am
ORD
- YUL
1 stop5h 20m
Air Canada
Deal found 3/10![Air Canada logo]()
$190
This Mytrip deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週四 4/99:15 am
YUL
- ORD
1 stop4h 50m
Air Canada
週日 4/127:55 am
ORD
- YUL
1 stop4h 26m
Air Canada
Deal found 3/9![Air Canada logo]()
$191
This Trip.com deal was found by Cheapflights users on 3/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 6/54:30 pm
YUL
- ORD
1 stop4h 46m
Air Canada
週一 6/87:25 am
ORD
- YUL
1 stop5h 20m
Air Canada
Deal found 3/12![Air Canada logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
週五 6/56:30 am
YUL
- MDW
1 stop4h 10m
Porter Airlines
週日 6/73:20 pm
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 3/11![Porter Airlines logo]()
$193
This FlightHub deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週三 4/156:50 am
YUL
- MDW
1 stop4h 25m
Porter Airlines
週五 4/244:05 pm
MDW
- YUL
1 stop5h 40m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$194
This SmartFares deal was found by Cheapflights users on 3/13. 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.
週五 4/109:15 am
YUL
- ORD
Nonstop2h 38m
Air Canada
週一 4/138:40 am
ORD
- YUL
Nonstop2h 11m
Air Canada
Deal found 3/13![Air Canada logo]()
$195
This Trip.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週一 3/309:15 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週三 4/111:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/9![Porter Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
週三 5/206:30 am
YUL
- MDW
1 stop4h 10m
Porter Airlines
週二 5/2610:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 3/13![Porter Airlines logo]()
$196
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 3月 14, 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 3月 14, 2026.
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週二 4/145:00 pm
YUL
- ORD
Nonstop2h 52m
United Airlines
週二 4/217:13 am
ORD
- YUL
Nonstop2h 27m
United Airlines
Deal found 3/9![United Airlines logo]()
$200
This FlightHub deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週三 4/19:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週二 4/711:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週三 4/86:30 am
YYC
- ORD
1 stop10h 32m
Delta
週三 4/152:09 pm
ORD
- YYC
1 stop9h 51m
Delta
Deal found 3/9![Delta logo]()
$232
This FlightHub deal was found by Cheapflights users on 3/12. 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.
週五 4/102:30 pm
YTZ
- MDW
Nonstop1h 50m
Multiple Airlines
週五 4/174:05 pm
MDW
- YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$260
This KAYAK deal was found by Cheapflights users on 3/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 6/17:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
週五 6/52:00 pm
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 3/13![Air Canada logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 4/151:45 pm
YVR
- ORD
1 stop8h 14m
Alaska Airlines
週六 4/186:00 am
ORD
- YVR
1 stop8h 45m
Alaska Airlines
Deal found 3/9![Alaska Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週四 4/96:10 am
YUL
- ORD
Nonstop2h 50m
United Airlines
週日 4/127:13 am
ORD
- YUL
Nonstop2h 27m
United Airlines
Deal found 3/9![United Airlines logo]()
$200
This FlightHub deal was found by Cheapflights users on 3/13. 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.
週五 4/172:30 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週一 4/2011:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/13![Porter Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週二 3/3112:50 pm
YUL
- MDW
1 stop6h 04m
Delta
週五 4/36:34 pm
MDW
- YUL
1 stop3h 39m
Delta
Deal found 3/9![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
週五 4/246:35 pm
YUL
- ORD
1 stop6h 08m
United Airlines
週日 4/267:13 am
ORD
- YUL
Nonstop2h 27m
United Airlines
Deal found 3/11![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
週六 4/2512:42 pm
YUL
- MDW
1 stop10h 46m
Delta
週一 4/275:21 pm
MDW
- YUL
1 stop5h 30m
Delta
Deal found 3/11![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 3/12. 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.
週五 4/171:27 pm
YYC
- ORD
1 stop10h 03m
United Airlines
週二 4/218:42 am
ORD
- YYC
Nonstop3h 50m
United Airlines
Deal found 3/12![United Airlines logo]()
$227
This Porter Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 9/710:05 am
YTZ
- ORD
Nonstop1h 55m
Porter Airlines
週一 9/147:00 am
ORD
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/12![Porter Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週五 5/226:00 am
YUL
- MDW
1 stop3h 43m
Delta
週一 5/256:23 am
MDW
- YUL
1 stop10h 19m
Delta
Deal found 3/9![Delta logo]()
$237
This Porter Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週二 4/289:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週三 4/2911:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週二 3/316:10 am
YUL
- ORD
Nonstop2h 50m
United Airlines
週六 4/46:01 pm
ORD
- YUL
Nonstop2h 25m
United Airlines
Deal found 3/10![United Airlines logo]()
$230
This KAYAK deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週六 4/252:15 pm
YYZ
- ORD
Nonstop2h 00m
Air Canada
週五 5/18:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 3/9![Air Canada logo]()
$308
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/1812:42 pm
YUL
- ORD
1 stop7h 06m
Delta
週二 4/2111:19 am
ORD
- YUL
1 stop5h 21m
Delta
Deal found 3/13![Delta logo]()
$249
This Porter Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週五 4/242:30 pm
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週五 5/13:20 pm
MDW
- YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$252
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週二 4/76:10 am
YUL
- ORD
Nonstop2h 50m
United Airlines
週四 4/96:00 am
ORD
- YUL
1 stop6h 09m
United Airlines
Deal found 3/9![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/1812:42 pm
YUL
- MDW
1 stop10h 46m
Delta
週二 4/2112:52 pm
MDW
- YUL
1 stop9h 59m
Delta
Deal found 3/13![Delta logo]()
$249
This Trip.com deal was found by Cheapflights users on 3/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 4/239:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週一 4/2711:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/12![Porter Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
週四 4/1612:00 pm
YTZ
- ORD
2 stops24h 42m
Multiple Airlines
週日 4/1912:47 pm
ORD
- YTZ
1 stop5h 08m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週六 4/186:35 pm
YUL
- ORD
1 stop6h 08m
United Airlines
週二 4/219:00 am
ORD
- YUL
1 stop6h 10m
United Airlines
Deal found 3/10![United Airlines logo]()
$236
This Flightnetwork deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週六 6/207:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
週二 6/238:45 am
ORD
- YTZ
1 stop6h 06m
Air Canada
Deal found 3/9![Air Canada logo]()
$350
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 4/171:45 pm
YVR
- ORD
1 stop8h 14m
Alaska Airlines
週六 4/186:00 am
ORD
- YVR
1 stop8h 45m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週六 6/66:00 am
YUL
- MDW
1 stop7h 42m
Delta
週五 6/121:05 pm
MDW
- YUL
1 stop9h 51m
Delta
Deal found 3/10![Delta logo]()
$251
This Trip.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週三 4/19:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週日 4/511:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/9![Porter Airlines logo]()
$253
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
週三 4/16:35 pm
YUL
- ORD
1 stop6h 08m
United Airlines
週日 4/56:01 pm
ORD
- YUL
Nonstop2h 25m
United Airlines
Deal found 3/11![United Airlines logo]()
$236
This Air Canada deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週四 8/207:20 pm
YTZ
- ORD
Nonstop1h 56m
Air Canada
週日 8/237:25 am
ORD
- YTZ
Nonstop1h 41m
Air Canada
Deal found 3/9![Air Canada logo]()
$360
Last-minute flights from Canada to ChicagoDiscover last-minute flight deals from Canada to Chicago. Data last updated 3月 14, 2026 and is based on user searches.
Discover last-minute flight deals from Canada to Chicago. Data last updated 3月 14, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週一 3/309:15 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週三 4/111:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/9![Porter Airlines logo]()
$196
This Trip.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週二 4/76:50 am
YUL
- MDW
1 stop4h 25m
Porter Airlines
週四 4/911:00 am
MDW
- YUL
1 stop4h 30m
Porter Airlines
Deal found 3/9![Porter Airlines logo]()
$197
This Trip.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週三 4/89:15 am
YUL
- ORD
Nonstop2h 38m
Air Canada
週三 4/1512:50 pm
ORD
- YUL
Nonstop2h 15m
Air Canada
Deal found 3/9![Air Canada logo]()
$193
This Mytrip deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週四 4/99:15 am
YUL
- ORD
1 stop4h 50m
Air Canada
週日 4/127:55 am
ORD
- YUL
1 stop4h 26m
Air Canada
Deal found 3/9![Air Canada logo]()
$191
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週四 4/96:10 am
YUL
- ORD
Nonstop2h 50m
United Airlines
週日 4/127:13 am
ORD
- YUL
Nonstop2h 27m
United Airlines
Deal found 3/9![United Airlines logo]()
$200
This SmartFares deal was found by Cheapflights users on 3/13. 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.
週五 4/109:15 am
YUL
- ORD
Nonstop2h 38m
Air Canada
週一 4/138:40 am
ORD
- YUL
Nonstop2h 11m
Air Canada
Deal found 3/13![Air Canada logo]()
$195
This Super.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週一 4/139:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週三 4/2211:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$197
This FlightHub deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週三 4/156:50 am
YUL
- MDW
1 stop4h 25m
Porter Airlines
週五 4/244:05 pm
MDW
- YUL
1 stop5h 40m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$194
This Mytrip deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週四 4/169:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
週一 4/2011:00 am
MDW
- YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/9![Porter Airlines logo]()
$199
This Trip.com deal was found by Cheapflights users on 3/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 4/166:50 am
YUL
- MDW
1 stop4h 25m
Porter Airlines
週一 4/2011:00 am
MDW
- YUL
1 stop5h 45m
Porter Airlines
Deal found 3/12![Porter Airlines logo]()
$199
This Trip.com deal was found by Cheapflights users on 3/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 4/2610:55 am
YUL
- MDW
1 stop5h 25m
Porter Airlines
週日 5/310:25 am
MDW
- YUL
1 stop5h 50m
Porter Airlines
Deal found 3/12![Porter Airlines logo]()
$198
This FlightHub deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週四 4/3012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
週四 5/75:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 3/10![WestJet logo]()
$186
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 3月 14, 2026.
Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Data last updated 3月 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
週日 5/1012:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 3/13![WestJet logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
週日 4/2612:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 3/11![WestJet logo]()
$116
This SmartFares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週三 4/19:15 am
YUL
- ORD
Nonstop2h 38m
Air Canada
Deal found 3/9![Air Canada logo]()
$117
This Mytrip deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週五 4/1711:10 am
YUL
- ORD
1 stop5h 05m
Air Canada
Deal found 3/9![Air Canada logo]()
$119
This Trip.com deal was found by Cheapflights users on 3/13. 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.
週五 5/16:30 am
YUL
- MDW
1 stop4h 10m
Porter Airlines
Deal found 3/13![Porter Airlines logo]()
$120
This Mytrip deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週六 5/169:45 am
YUL
- ORD
2 stops8h 14m
Air Canada
Deal found 3/10![Air Canada logo]()
$121
This Trip.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週三 4/226:50 am
YUL
- MDW
1 stop4h 25m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$123
This Trip.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週六 4/411:20 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$124
This Trip.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週四 4/99:25 am
YTZ
- MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/10![Porter Airlines logo]()
$125
This eDestinos deal was found by Cheapflights users on 3/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 5/3110:35 am
YUL
- MDW
1 stop5h 00m
Porter Airlines
Deal found 3/12![Porter Airlines logo]()
$125
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
週四 5/712:34 pm
YYC
- ORD
Nonstop3h 27m
United Airlines
Deal found 3/10![United Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
週四 5/77:30 am
YVR
- ORD
1 stop7h 10m
WestJet
Deal found 3/9![WestJet logo]()
$126
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 3月 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Mytrip) |
One-way from | $115 (Kiwi.com) |
Popular in | December |
Cheapest in | July |
Average price | $264 |
Good round-trip deal | $194 or less |
Good one-way deal | $112 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 3月 14, 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
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週二 4/14
5:00 pm-6:52 pm
Nonstop2h 52m
Chicago O'Hare Intl
週二 4/21
7:13 am-10:40 am
Nonstop2h 27m
$200
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週四 4/9
6:10 am-8:00 am
Nonstop2h 50m
Chicago O'Hare Intl
週日 4/12
7:13 am-10:40 am
Nonstop2h 27m
$200
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週五 4/24
6:35 pm-11:43 pm
1 stop6h 08m
Chicago O'Hare Intl
週日 4/26
7:13 am-10:40 am
Nonstop2h 27m
$217
CalgaryChicago
YYC - ORD
YYCORD
Calgary
週五 4/17
1:27 pm-12:30 am
1 stop10h 03m
Chicago O'Hare Intl
週二 4/21
8:42 am-11:32 am
Nonstop3h 50m
$227
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
週三 4/1
9:25 am-10:15 am
Nonstop1h 50m
Chicago Midway
週二 4/7
11:00 am-1:42 pm
Nonstop1h 42m
$229
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
週五 4/17
2:30 pm-3:20 pm
Nonstop1h 50m
Chicago Midway
週一 4/20
11:00 am-1:42 pm
Nonstop1h 42m
$230
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週二 3/31
6:10 am-8:00 am
Nonstop2h 50m
Chicago O'Hare Intl
週六 4/4
6:01 pm-9:26 pm
Nonstop2h 25m
$230
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週二 4/7
6:10 am-8:00 am
Nonstop2h 50m
Chicago O'Hare Intl
週四 4/9
6:00 am-1:09 pm
1 stop6h 09m
$231
CalgaryChicago
YYC - ORD
YYCORD
Calgary
週三 4/8
6:30 am-6:02 pm
1 stop10h 32m
Chicago O'Hare Intl
週三 4/15
2:09 pm-11:00 pm
1 stop9h 51m
$232
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
週二 3/31
12:50 pm-5:54 pm
1 stop6h 04m
Chicago Midway
週五 4/3
6:34 pm-11:13 pm
1 stop3h 39m
$236
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.
YUL-ORD
YTZ-MDW
YYC-ORD
YTZ-ORD
YVR-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
YUL-ORD
YTZ-MDW
YYC-ORD
YTZ-ORD
What is the cheapest month to book a flight from Canada to Chicago?
Currently, June is the cheapest month in which you can book a flight from Canada to Chicago (average of $83). Flying from Canada to Chicago in July is currently the most expensive (average of $146). 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 3月 14, 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 28% 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 March 14, 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. Monday 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 3月 14, 2026.
The most flights from CA0 to CHI are scheduled on a Wednesday (63 on average). You will have fewer flight options on Saturday, 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 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?
Tuesday tends to have the lowest number of delays on this route, whereas Saturday 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 3月 14, 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
Boarding
8.2
Overall
8.0
Entertainment
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Food
7.6
Boarding
8.2
Overall
8.0
Entertainment
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Related info for your journey
Find useful and relevant information for your journey from 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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 3月 14, 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 3月 14, 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 3月 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$336 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$83 | Average$381 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$90 | Average$408 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$242 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$167 | Average$373 | FlexibilityNo cancel fee | On-time71% |