$93+ Cheap flights from Chicago (CHI) to Hamilton, ON, Canada
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Jun 20 — Jun 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Hamilton with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Hamilton are usually found in November or July, booked 68 days in advance, depart on a Thursday or Wednesday and return on a Friday
Cheap flight deals from Chicago to Hamilton
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Best
Last-minute
One-way
Cheapest flights from Chicago to HamiltonExplore the most affordable flight options available from Chicago to Hamilton. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.
Explore the most affordable flight options available from Chicago to Hamilton. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.
This Booking.com deal was found by Cheapflights users on 5/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:40 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Tue 6/2312:25 pm
YYZ
- ORD
Nonstop1h 57m
Air Canada
Deal found 5/17![Air Canada logo]()
$229
This Mytrip deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Sun 6/148:00 am
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 5/18![Air Canada logo]()
$233
This Flightnetwork deal was found by Cheapflights users on 5/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Sun 5/318:00 am
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 5/16![Air Canada logo]()
$236
This Air Canada deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Sat 6/208:05 am
YYZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 5/20![Air Canada logo]()
$239
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
Delta
Deal found 5/20![Delta logo]()
$269
This Billigflug deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- YYZ
1 stop7h 07m
Air France
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
Air France
Deal found 5/20![Air France logo]()
$275
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:22 am
MDW
- YYZ
1 stop4h 52m
Delta
Sat 6/1312:09 pm
YYZ
- MDW
1 stop7h 02m
Delta
Deal found 5/20![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
Delta
Deal found 5/18![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:35 pm
MDW
- YYZ
1 stop3h 27m
Delta
Sat 6/276:05 am
YYZ
- MDW
1 stop7h 41m
Delta
Deal found 5/20![Delta logo]()
$307
This Kissandfly.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- YYZ
1 stop7h 07m
KLM
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
KLM
Deal found 5/20![KLM logo]()
$311
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/199:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Sat 7/112:24 pm
YYZ
- MDW
1 stop4h 43m
Delta
Deal found 5/18![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:30 am
MDW
- YYZ
1 stop6h 53m
Delta
Sun 9/136:00 am
YYZ
- MDW
1 stop7h 30m
Delta
Deal found 5/18![Delta logo]()
$329
Best flights from Chicago to HamiltonDiscover carefully curated flight deals from Chicago to Hamilton that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 21, 2026.
Discover carefully curated flight deals from Chicago to Hamilton that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 21, 2026.
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:52 am
ORD
- YYZ
1 stop7h 32m
Delta
Thu 6/2512:09 pm
YYZ
- ORD
1 stop7h 20m
Delta
Deal found 5/20![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/119:20 pm
ORD
- YYZ
Nonstop1h 39m
United Airlines
Sun 6/148:45 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 5/20![United Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:52 am
ORD
- YYZ
1 stop7h 32m
Delta
Sun 6/1412:09 pm
YYZ
- ORD
1 stop7h 20m
Delta
Deal found 5/20![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 5/16. 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.
Sun 6/284:37 pm
ORD
- YYZ
Nonstop2h 00m
United Airlines
Sat 7/411:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 5/16![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:22 pm
ORD
- YYZ
1 stop4h 40m
Delta
Sun 6/1412:09 pm
YYZ
- ORD
1 stop7h 20m
Delta
Deal found 5/19![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:09 am
ORD
- YYZ
Nonstop1h 45m
United Airlines
Fri 8/148:50 am
YYZ
- ORD
Nonstop2h 03m
United Airlines
Deal found 5/17![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:17 am
MDW
- YYZ
1 stop3h 17m
Delta
Sat 6/136:05 am
YYZ
- MDW
1 stop7h 41m
Delta
Deal found 5/19![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:50 am
ORD
- YYZ
1 stop4h 53m
United Airlines
Sun 8/167:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 5/19![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:22 am
MDW
- YYZ
1 stop6h 59m
Delta
Wed 6/34:04 pm
YYZ
- MDW
1 stop3h 29m
Delta
Deal found 5/18![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:53 pm
ORD
- YYZ
1 stop7h 01m
United Airlines
Sun 7/197:00 am
YYZ
- ORD
Nonstop2h 00m
United Airlines
Deal found 5/20![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:26 pm
MDW
- YYZ
1 stop8h 36m
Delta
Tue 6/166:05 am
YYZ
- MDW
1 stop7h 41m
Delta
Deal found 5/18![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2411:30 am
ORD
- YYZ
1 stop4h 54m
Delta
Fri 6/269:45 am
YYZ
- ORD
1 stop7h 41m
Delta
Deal found 5/20![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/103:53 pm
ORD
- YYZ
1 stop7h 01m
United Airlines
Fri 7/177:43 pm
YYZ
- ORD
1 stop4h 48m
United Airlines
Deal found 5/20![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:01 am
ORD
- YYZ
1 stop7h 18m
Delta
Mon 6/299:45 am
YYZ
- ORD
1 stop4h 19m
Delta
Deal found 5/19![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/16. 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 7/111:30 am
ORD
- YYZ
1 stop4h 54m
Delta
Fri 7/246:10 am
YYZ
- ORD
1 stop5h 27m
Delta
Deal found 5/16![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Fri 7/1012:09 pm
YYZ
- MDW
1 stop7h 16m
Delta
Deal found 5/19![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/16. 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.
Tue 6/309:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Wed 7/224:10 pm
YYZ
- MDW
1 stop3h 15m
Delta
Deal found 5/16![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/16. 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 7/39:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Tue 7/214:10 pm
YYZ
- MDW
1 stop3h 15m
Delta
Deal found 5/16![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:19 am
MDW
- YYZ
1 stop7h 05m
Delta
Wed 7/229:45 am
YYZ
- MDW
1 stop3h 53m
Delta
Deal found 5/17![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/16. 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.
Thu 7/29:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Mon 7/2012:09 pm
YYZ
- MDW
1 stop7h 16m
Delta
Deal found 5/16![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/16. 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.
Mon 6/299:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Mon 7/2012:09 pm
YYZ
- MDW
1 stop7h 16m
Delta
Deal found 5/16![Delta logo]()
$372
This Delta deal was found by Cheapflights users on 5/16. 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.
Mon 6/299:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Thu 7/239:45 am
YYZ
- MDW
1 stop3h 53m
Delta
Deal found 5/16![Delta logo]()
$372
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:17 am
MDW
- YYZ
1 stop3h 17m
Delta
Thu 6/256:05 am
YYZ
- MDW
1 stop4h 09m
Delta
Deal found 5/20![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:26 pm
MDW
- YYZ
1 stop8h 36m
Delta
Tue 6/306:05 am
YYZ
- MDW
1 stop4h 09m
Delta
Deal found 5/18![Delta logo]()
$382
Last-minute flights from Chicago to HamiltonDiscover last-minute flight deals from Chicago to Hamilton. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hamilton. Data last updated May 21, 2026 and is based on user searches.
This Flightnetwork deal was found by Cheapflights users on 5/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Sun 5/318:00 am
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 5/16![Air Canada logo]()
$236
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:22 am
MDW
- YYZ
1 stop4h 52m
Delta
Sat 6/1312:09 pm
YYZ
- MDW
1 stop7h 02m
Delta
Deal found 5/20![Delta logo]()
$286
This Mytrip deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Sun 6/148:00 am
YYZ
- ORD
Nonstop2h 00m
Air Canada
Deal found 5/18![Air Canada logo]()
$233
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
Delta
Deal found 5/18![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
Delta
Deal found 5/20![Delta logo]()
$269
This Billigflug deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- YYZ
1 stop7h 07m
Air France
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
Air France
Deal found 5/20![Air France logo]()
$275
This Kissandfly.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- YYZ
1 stop7h 07m
KLM
Sun 6/1412:09 pm
YYZ
- MDW
1 stop7h 22m
KLM
Deal found 5/20![KLM logo]()
$311
This Air Canada deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Sat 6/208:05 am
YYZ
- ORD
Nonstop1h 55m
Air Canada
Deal found 5/20![Air Canada logo]()
$239
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Sun 6/286:05 am
YYZ
- MDW
1 stop7h 41m
Delta
Deal found 5/20![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/199:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Sat 7/112:24 pm
YYZ
- MDW
1 stop4h 43m
Delta
Deal found 5/18![Delta logo]()
$324
This Booking.com deal was found by Cheapflights users on 5/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:40 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Tue 6/2312:25 pm
YYZ
- ORD
Nonstop1h 57m
Air Canada
Deal found 5/17![Air Canada logo]()
$229
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:35 pm
MDW
- YYZ
1 stop3h 27m
Delta
Sat 6/276:05 am
YYZ
- MDW
1 stop7h 41m
Delta
Deal found 5/20![Delta logo]()
$307
One-way flights from Chicago to HamiltonSearch for one-way flight options from Chicago to Hamilton. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
Search for one-way flight options from Chicago to Hamilton. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
This Air Canada deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:20 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 5/19![Air Canada logo]()
$93
This Flightnetwork deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/203:45 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Deal found 5/18![Air Canada logo]()
$100
This Booking.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:25 pm
ORD
- YYZ
Nonstop1h 43m
Air Canada
Deal found 5/18![Air Canada logo]()
$102
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:52 am
ORD
- YYZ
1 stop7h 32m
Delta
Deal found 5/20![Delta logo]()
$105
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:17 am
MDW
- YYZ
1 stop7h 07m
Delta
Deal found 5/20![Delta logo]()
$105
This Flightnetwork deal was found by Cheapflights users on 5/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:55 am
ORD
- YYZ
Nonstop1h 40m
Air Canada
Deal found 5/16![Air Canada logo]()
$110
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:56 pm
ORD
- YYZ
Nonstop2h 00m
United Airlines
Deal found 5/18![United Airlines logo]()
$113
This Mytrip deal was found by Cheapflights users on 5/17. 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.
Mon 7/132:15 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Deal found 5/17![Air Canada logo]()
$118
This Booking.com deal was found by Cheapflights users on 5/16. 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.
Tue 6/309:50 am
ORD
- YYZ
Nonstop1h 45m
Air Canada
Deal found 5/16![Air Canada logo]()
$119
This Booking.com deal was found by Cheapflights users on 5/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/288:40 pm
ORD
- YYZ
Nonstop1h 46m
Air Canada
Deal found 5/17![Air Canada logo]()
$120
This Air Canada deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:50 am
ORD
- YYZ
Nonstop1h 45m
Air Canada
Deal found 5/20![Air Canada logo]()
$121
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/249:17 am
MDW
- YYZ
1 stop3h 17m
Delta
Deal found 5/18![Delta logo]()
$122
Find flight deals from Chicago to Hamilton
Keep the following information in mind while searching for Chicago to Hamilton flight deals. Data was last updated May 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $229 (Booking.com) |
One-way from | $93 (Air Canada) |
Popular in | March |
Cheapest in | November |
Average price | $338 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Hamilton 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 May 21, 2026.
Use the filters below to find and compare flights from Chicago to Hamilton that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 6/18
8:52 am-5:24 pm
1 stop7h 32m
Toronto Pearson Intl
Thu 6/25
12:09 pm-6:29 pm
1 stop7h 20m
$269
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 6/11
8:52 am-5:24 pm
1 stop7h 32m
Toronto Pearson Intl
Sun 6/14
12:09 pm-6:29 pm
1 stop7h 20m
$269
Quickest round-trip
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 6/11
9:20 pm-11:59 pm
Nonstop1h 39m
Toronto Pearson Intl
Sun 6/14
8:45 am-9:45 am
Nonstop2h 00m
$278
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Fri 6/12
5:22 pm-11:02 pm
1 stop4h 40m
Toronto Pearson Intl
Sun 6/14
12:09 pm-6:29 pm
1 stop7h 20m
$303
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Wed 6/10
9:17 am-1:34 pm
1 stop3h 17m
Toronto Pearson Intl
Sat 6/13
6:05 am-12:46 pm
1 stop7h 41m
$303
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Mon 6/1
9:22 am-5:21 pm
1 stop6h 59m
Toronto Pearson Intl
Wed 6/3
4:04 pm-6:33 pm
1 stop3h 29m
$303
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Thu 6/11
1:26 pm-11:02 pm
1 stop8h 36m
Toronto Pearson Intl
Tue 6/16
6:05 am-12:46 pm
1 stop7h 41m
$303
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Wed 6/24
11:30 am-5:24 pm
1 stop4h 54m
Toronto Pearson Intl
Fri 6/26
9:45 am-4:26 pm
1 stop7h 41m
$307
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Sun 6/28
4:37 pm-7:37 pm
Nonstop2h 00m
Toronto Pearson Intl
Sat 7/4
11:00 am-12:00 pm
Nonstop2h 00m
$319
ChicagoToronto
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Wed 8/12
7:09 am-9:54 am
Nonstop1h 45m
Toronto Pearson Intl
Fri 8/14
8:50 am-9:53 am
Nonstop2h 03m
$319
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Hamilton
Have a flexible travel schedule? Discover the best time to fly to Hamilton from Chicago with our price prediction graph.
ORD-YYZ
MDW-YYZ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Hamilton
CHI-H4M
ORD-YYZ
MDW-YYZ
What is the cheapest time of day to fly from CHI to H4M?
Find hourly flight availability from Chicago to Hamilton. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 21, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Hamilton in the morning. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight at noon.
Weekly flight availability from Chicago to Hamilton
Explore weekly flight availability from Chicago to Hamilton. 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 May 21, 2026.
The most flights from CHI to H4M are scheduled on a Thursday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (46 on average).
How much does it cost to fly round-trip from Chicago to Hamilton?
What is the cheapest day to fly from Chicago to Hamilton?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Hamilton. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Chicago to Hamilton flight should consider departing on Saturday mornings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Hamilton
Get insights into the airlines that provide service to Hamilton. 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 Hamilton. Reviews last updated May 21, 2026.
Read through reviews of airlines operating flights from Chicago to Hamilton, such as Porter Airlines,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Food
7.6
Entertainment
7.0
Crew
8.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Food
7.6
Entertainment
7.0
Crew
8.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Food
7.6
Entertainment
7.0
Crew
8.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Food
7.6
Entertainment
7.0
Crew
8.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Comfort
8.0
Overall
8.0
Food
7.6
Entertainment
7.0
Crew
8.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Related info for your journey
Find useful and relevant information for your journey from Chicago to Hamilton. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Hamilton
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Complete your trip
Complete your trip to Hamilton by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Hamilton by cabin class
Find flights from Chicago to Hamilton, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Hamilton flights
Browse other Chicago and Hamilton flight options. Last updated on May 21, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Chicago to Hamilton
Discover the top 7 airlines that operate flights from Chicago to Hamilton. 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 May 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$303 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$94 | Average$341 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$149 | Average$291 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$403 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$170 | Average$319 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$172 | Average$371 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$209 | Average$369 | FlexibilityNo cancel fee | On-time71% |