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$83+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Jun 7 — Jun 141
Sat 6/7
Sat 6/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Hamilton are usually found in April or October, booked 68 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Chicago to Hamilton

Keep the following information in mind while searching for Chicago to Hamilton flight deals. Data was last updated June 2, 2025.

Round-trip from

$200
(United Airlines)

One-way from

$83
(Mytrip)

Popular in

November

Cheapest in

April

Average price

$292
From Chicago (CHI) to Hamilton
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One-way flight from Chicago (CHI) to Hamilton
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Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Chicago to Hamilton

Cheapest flights from Chicago to Hamilton
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 June 2, 2025.

This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/51:05 pmORD - YYZ
Nonstop1h 41mUnited Airlines
Thu 9/112:45 pmYYZ - ORD
Nonstop2h 03mUnited Airlines
Deal found 6/2$167
This Flightnetwork deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/152:00 pmORD - YYZ
Nonstop1h 44mAir Canada
Tue 7/228:15 amYYZ - ORD
Nonstop1h 54mAir Canada
Deal found 6/1$202
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Wed 7/95:00 amORD - YYZ
1 stop4h 20mAmerican Airlines
Wed 7/91:20 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
Deal found 6/1$206
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/299:10 amORD - YYZ
1 stop3h 22mDelta
Tue 9/26:15 amYYZ - ORD
1 stop6h 30mDelta
Deal found 6/1$245
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 9/169:20 amMDW - YYZ
1 stop8h 07mDelta
Mon 9/2212:15 pmYYZ - MDW
1 stop7h 21mDelta
Deal found 6/1$245
This Mytrip deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/155:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
Tue 7/226:30 amYYZ - ORD
2 stops34h 12mMultiple Airlines
Deal found 6/1$306
This Flysmarter deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/265:29 amORD - YYZ
1 stop4h 43mBritish Airways
Sun 6/2911:52 amYYZ - ORD
1 stop6h 43mBritish Airways
Deal found 6/2$319
This Sun Country Air deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2511:50 amORD - YYZ
1 stop21h 50mSun Country Air
Thu 7/311:40 amYYZ - ORD
1 stop26h 11mSun Country Air
Deal found 6/2$361
This Kissandfly.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/268:50 amORD - YYZ
Nonstop1h 59mLufthansa
Sun 6/292:45 pmYYZ - ORD
Nonstop2h 05mLufthansa
Deal found 6/1$366
This Justfly.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/19:24 amMDW - YYZ
1 stop8h 10mWestJet
Mon 8/187:45 amYYZ - MDW
1 stop15h 04mWestJet
Deal found 6/1$437
This CheapTicketsDeal deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/309:24 amMDW - YYZ
1 stop8h 10mMultiple Airlines
Mon 7/76:30 amYYZ - MDW
1 stop6h 59mMultiple Airlines
Deal found 6/1$449

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 June 2, 2025.
Use the filters below to find and compare flights from Chicago to Hamilton that are best for you.

Fly from

Chicago

Fly to

Hamilton

Route

Depart

Return

Price

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 8/29

9:12 pm-11:58 pm

Nonstop1h 46m

Toronto Pearson Intl

Tue 9/2

5:15 pm-6:12 pm

Nonstop1h 57m

$200

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 7/15

2:00 pm-4:44 pm

Nonstop1h 44m

Toronto Pearson Intl

Tue 7/22

8:15 am-9:09 am

Nonstop1h 54m

$202

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 7/9

5:00 am-10:20 am

1 stop4h 20m

Toronto Pearson Intl

Wed 7/9

1:20 pm-2:15 pm

Nonstop1h 55m

$206

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 8/29

9:10 am-1:32 pm

1 stop3h 22m

Toronto Pearson Intl

Tue 9/2

6:15 am-11:45 am

1 stop6h 30m

$245

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/16

9:20 am-6:27 pm

1 stop8h 07m

Toronto Pearson Intl

Mon 9/22

12:15 pm-6:36 pm

1 stop7h 21m

$245

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 7/15

5:05 am-2:05 pm

1 stop8h 00m

Toronto Pearson Intl

Tue 7/22

6:30 am-3:42 pm

2 stops34h 12m

$306

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 6/26

5:29 am-11:12 am

1 stop4h 43m

Toronto Pearson Intl

Sun 6/29

11:52 am-5:35 pm

1 stop6h 43m

$319

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 6/25

11:50 am-10:40 am

1 stop21h 50m

Toronto Pearson Intl

Thu 7/3

11:40 am-12:51 pm

1 stop26h 11m

$361

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 8/1

9:24 am-6:34 pm

1 stop8h 10m

Toronto Pearson Intl

Mon 8/18

7:45 am-9:49 pm

1 stop15h 04m

$437

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 6/30

9:24 am-6:34 pm

1 stop8h 10m

Toronto Pearson Intl

Mon 7/7

6:30 am-12:29 pm

1 stop6h 59m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 21 results
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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.
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

How far ahead should I book a flight from Chicago to Hamilton?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Hamilton. Price data was last updated on May 23, 2025.

Booking 68 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Hamilton. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Hamilton?

Currently, January is the cheapest month in which you can book a flight from Chicago to Hamilton (average of $243). Flying from Chicago to Hamilton in July is currently the most expensive (average of $356). 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 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 June 2, 2025.

When flying from Chicago to Hamilton, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 June 1, 2025.

Travelers seeking maximum savings on their Chicago to Hamilton flight should consider departing on Friday mornings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 June 2, 2025.

The most flights from CHI to H4M are scheduled on a Monday (65 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (39 on average).

Rainfall in Hamilton by month

Plan your trip to Hamilton by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Hamilton ranges from 2.0 - 3.3 inches per month. June is typically the wettest month, when rainfall can reach 3.3 in. February is typically the driest time to visit Hamilton when rainfall is around 2.0 in.

Temperature in Hamilton by month

Plan your trip to Hamilton by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Hamilton, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 June 2, 2025.
Read reviews from past customers who have flown Delta, United Airlines and American Airlines from Chicago to Hamilton. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,955 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,955 reviews
Delta
8.0
Very good
7,955 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,767 reviews
Delta
8.0
Very good
7,955 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,955 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,862 reviews
Delta
8.0
Very good
7,955 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,474 reviews
Delta
8.0
Very good
7,955 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Chicago to Hamilton one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $83. Users have also found prices from $91 and $101 on United Airlines and Delta, respectively.

  • What are the most reliable airlines from Chicago to Hamilton?

    The top 3 most reliable airlines when flying from Chicago to Hamilton are Royal Jordanian (97%), SkyWest Airlines (94%) and Korean Air (93%).

  • What are the cheapest flights from Chicago to Hamilton?

    Looking at all options, your cheapest flight can be booked for $69. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $150 on average our data indicates $1,329 when flying from Chicago to Hamilton.

  • Can I find deals for flights from Chicago to Hamilton that include hotel bookings?

    Yes. In addition to deals on Chicago to Hamilton flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Hamilton?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Hamilton.

  • Can I find deals for business class flights from Chicago to Hamilton?

    Yes. Cheapflights offers flight deals from Chicago to Hamilton by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Hamilton?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Hamilton (average of $243). Flying from Chicago to Hamilton in July is currently the most expensive (average of $356). 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.

See more FAQs

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Alternative routes for Chicago to Hamilton

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Pearson Intl flights
Midway to Toronto Island flights
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Midway to Pearson Intl flights
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St. Louis to Pearson Intl flights
O'Hare Intl to Ottawa flights
Midway to Ottawa flights
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O'Hare Intl to Thunder Bay flights
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Midway to Thunder Bay flights
Evansville to Pearson Intl flights
Evansville to Pierre Elliott Trudeau Intl flights
Springfield to Pearson Intl flights
Bloomington to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Kingston flights
Bloomington to Ottawa flights
Dubuque to Pearson Intl flights

Top 4 airlines flying from Chicago to Hamilton

Discover the top 4 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 June 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$109Average$280FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$117Average$534FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$134Average$337FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$146Average$368FlexibilityNo cancel feeOn-time71%

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