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$104+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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The best prices from Chicago to Hamilton are usually found in October or August, booked 88 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 February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$195
(Mytrip)

One-way from

$104
(Kiwi.com)

Popular in

November

Cheapest in

October

Average price

$339
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
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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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 23, 2025.

This Mytrip deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/82:53 pmORD - YYZ
1 stop19h 52mMultiple Airlines
Tue 4/158:15 pmYYZ - ORD
1 stop12h 49mMultiple Airlines
Deal found 2/22$195
This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/163:00 pmMDW - YYZ
1 stop7h 54mMultiple Airlines
Sat 4/197:00 amYYZ - MDW
1 stop16h 36mMultiple Airlines
Deal found 2/22$241
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/247:26 amORD - YYZ
1 stop6h 55mUnited Airlines
Mon 3/246:40 pmYYZ - ORD
Nonstop1h 57mUnited Airlines
Deal found 2/22$254
This flygcity.se deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/95:59 pmORD - YYZ
1 stop4h 55mAir Canada
Wed 4/169:00 pmYYZ - ORD
Nonstop2h 06mAir Canada
Deal found 2/23$257
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/206:45 amORD - YYZ
1 stop8h 27mDelta
Sun 3/2310:20 amYYZ - ORD
1 stop3h 21mDelta
Deal found 2/22$297
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/89:23 amMDW - YYZ
1 stop5h 51mDelta
Tue 4/1512:24 pmYYZ - MDW
1 stop5h 55mDelta
Deal found 2/22$297
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/206:05 amORD - YYZ
1 stop4h 46mAmerican Airlines
Sun 3/236:15 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Deal found 2/23$309
This Trip.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/262:45 pmORD - YYZ
1 stop4h 46mWestJet
Sat 3/291:20 pmYYZ - ORD
1 stop3h 55mWestJet
Deal found 2/23$316
This Justfly.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2211:27 amMDW - YYZ
1 stop10h 32mWestJet
Sun 3/306:30 amYYZ - MDW
1 stop12h 48mWestJet
Deal found 2/22$336
This Kissandfly.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/209:50 amORD - YYZ
Nonstop1h 40mBritish Airways
Sun 3/236:15 amYYZ - ORD
Nonstop2h 15mBritish Airways
Deal found 2/22$364

Find flights from Chicago to Hamilton within your budget

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 February 23, 2025.

Fly from

Chicago

Fly to

Hamilton

Route

Depart

Return

Price

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 4/8

9:08 pm-11:45 am

1 stop13h 37m

Toronto Pearson Intl

Tue 4/15

8:15 pm-8:04 am

1 stop12h 49m

$195

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 4/16

3:00 pm-11:54 pm

1 stop7h 54m

Toronto Pearson Intl

Sat 4/19

7:00 am-10:36 pm

1 stop16h 36m

$241

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 3/24

7:26 am-3:21 pm

1 stop6h 55m

Toronto Pearson Intl

Mon 3/24

6:40 pm-7:37 pm

Nonstop1h 57m

$254

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 4/9

5:59 pm-11:54 pm

1 stop4h 55m

Toronto Pearson Intl

Wed 4/16

9:00 pm-10:06 pm

Nonstop2h 06m

$257

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 3/20

6:45 am-4:12 pm

1 stop8h 27m

Toronto Pearson Intl

Sun 3/23

10:20 am-12:41 pm

1 stop3h 21m

$297

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 4/8

9:23 am-4:14 pm

1 stop5h 51m

Toronto Pearson Intl

Tue 4/15

12:24 pm-5:19 pm

1 stop5h 55m

$297

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 3/20

6:05 am-11:51 am

1 stop4h 46m

Toronto Pearson Intl

Sun 3/23

6:15 am-7:30 am

Nonstop2h 15m

$309

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 3/26

2:45 pm-8:31 pm

1 stop4h 46m

Toronto Pearson Intl

Sat 3/29

1:20 pm-4:15 pm

1 stop3h 55m

$316

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 3/22

11:27 am-10:59 pm

1 stop10h 32m

Toronto Pearson Intl

Sun 3/30

6:30 am-6:18 pm

1 stop12h 48m

$336

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 3/20

9:50 am-12:30 pm

Nonstop1h 40m

Toronto Pearson Intl

Sun 3/23

6:15 am-7:30 am

Nonstop2h 15m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 22 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.

Travel insights for flights from Chicago to Hamilton

Get recent, data-driven insights about flights from Chicago to Hamilton including ideal travel times, pricing trends, and more.

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 February 14, 2025.

Booking 88 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 $359). 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 February 23, 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 February 16, 2025.

Travelers seeking maximum savings on their Chicago to Hamilton flight should consider departing on Wednesday evenings 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 February 23, 2025.

The most flights from CHI to H4M are scheduled on a Monday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 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 February 23, 2025.
Read reviews from past customers who have flown Japan Airlines, Delta and KLM from Chicago to Hamilton. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Japan Airlines
8.3
Very good
1,440 reviews

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Overall

8.3

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Diego,Nov 2024

HKG - NRT

overall very good; just found a bit poor the food options in Narita airport but the in the flight it was good but limited (no real choice to avoid seafood or clearly stay away from pork..); most of the food was tasty tho and the choice was nice, specially their snacks and dessert and drinks. The in-flight systems was so-so (too complicated interface; they should rehaul with a proper UIX), and I specially appreciated their segments of videos capsules about the behind the scenes including an overview of technicalities of their aircraft and days in the life of their pilots. It was refreshing and give a good ideas of the efforts and challenges every employees has to deal with. Loved it!

Japan Airlines
8.3
Very good
1,440 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Overall

8.3

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Diego,Nov 2024

HKG - NRT

overall very good; just found a bit poor the food options in Narita airport but the in the flight it was good but limited (no real choice to avoid seafood or clearly stay away from pork..); most of the food was tasty tho and the choice was nice, specially their snacks and dessert and drinks. The in-flight systems was so-so (too complicated interface; they should rehaul with a proper UIX), and I specially appreciated their segments of videos capsules about the behind the scenes including an overview of technicalities of their aircraft and days in the life of their pilots. It was refreshing and give a good ideas of the efforts and challenges every employees has to deal with. Loved it!

Delta
8.0
Very good
8,187 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Overall

8.3

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Diego,Nov 2024

HKG - NRT

overall very good; just found a bit poor the food options in Narita airport but the in the flight it was good but limited (no real choice to avoid seafood or clearly stay away from pork..); most of the food was tasty tho and the choice was nice, specially their snacks and dessert and drinks. The in-flight systems was so-so (too complicated interface; they should rehaul with a proper UIX), and I specially appreciated their segments of videos capsules about the behind the scenes including an overview of technicalities of their aircraft and days in the life of their pilots. It was refreshing and give a good ideas of the efforts and challenges every employees has to deal with. Loved it!

KLM
7.8
Good
1,333 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Overall

8.3

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Diego,Nov 2024

HKG - NRT

overall very good; just found a bit poor the food options in Narita airport but the in the flight it was good but limited (no real choice to avoid seafood or clearly stay away from pork..); most of the food was tasty tho and the choice was nice, specially their snacks and dessert and drinks. The in-flight systems was so-so (too complicated interface; they should rehaul with a proper UIX), and I specially appreciated their segments of videos capsules about the behind the scenes including an overview of technicalities of their aircraft and days in the life of their pilots. It was refreshing and give a good ideas of the efforts and challenges every employees has to deal with. Loved it!

United Airlines
7.4
Good
8,746 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Overall

8.3

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Diego,Nov 2024

HKG - NRT

overall very good; just found a bit poor the food options in Narita airport but the in the flight it was good but limited (no real choice to avoid seafood or clearly stay away from pork..); most of the food was tasty tho and the choice was nice, specially their snacks and dessert and drinks. The in-flight systems was so-so (too complicated interface; they should rehaul with a proper UIX), and I specially appreciated their segments of videos capsules about the behind the scenes including an overview of technicalities of their aircraft and days in the life of their pilots. It was refreshing and give a good ideas of the efforts and challenges every employees has to deal with. Loved it!

American Airlines
7.2
Good
10,000 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Comfort

8.2

Food

7.7

Boarding

8.4

Entertainment

7.8

Overall

8.3

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Diego,Nov 2024

HKG - NRT

overall very good; just found a bit poor the food options in Narita airport but the in the flight it was good but limited (no real choice to avoid seafood or clearly stay away from pork..); most of the food was tasty tho and the choice was nice, specially their snacks and dessert and drinks. The in-flight systems was so-so (too complicated interface; they should rehaul with a proper UIX), and I specially appreciated their segments of videos capsules about the behind the scenes including an overview of technicalities of their aircraft and days in the life of their pilots. It was refreshing and give a good ideas of the efforts and challenges every employees has to deal with. Loved it!

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 United Airlines. According to our data, you can fly for as low as $111. Users have also found prices from $117 and $121 on Air Canada 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 Egyptair (100%), Royal Jordanian (91%) and Copa Airlines (78%).

  • What are the cheapest flights from Chicago to Hamilton?

    Looking at all options, your cheapest flight can be booked for $106. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $215 on average our data indicates $1,038 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 $359). 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 Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
Midway to Pierre Elliott Trudeau Intl flights
Midway to Toronto Island flights
Midway to Pearson Intl flights
O'Hare Intl to Toronto Island flights
St. Louis to Pearson Intl flights
O'Hare Intl to Ottawa flights
St. Louis to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Hamilton flights
Midway to Ottawa flights
St. Louis to Ottawa flights
Moline to Pearson Intl flights
O'Hare Intl to London flights
Evansville to Pearson Intl flights
O'Hare Intl to Thunder Bay flights
Peoria to Pierre Elliott Trudeau Intl flights
Midway to Thunder Bay flights
Evansville to Pierre Elliott Trudeau Intl flights
Springfield to Pearson Intl flights
Champaign to Pearson Intl flights
Bloomington to Pierre Elliott Trudeau Intl flights
Bloomington to Ottawa flights
O'Hare Intl to Kingston 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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$122Average$267FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$122Average$343FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$122Average$544FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$145Average$357FlexibilityNo cancel feeOn-time69%
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