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$81+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Hamilton are usually found in June or November, booked 68 days in advance, depart on a Thursday or Friday 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 January 8, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$203
(United Airlines)

One-way from

$81
(Kiwi.com)

Popular in

January

Cheapest in

June

Average price

$381
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. 15% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This United Airlines deal was found by Cheapflights users on 1/6. 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 2/51:13 pmORD - YYZ
Nonstop1h 49mUnited Airlines
Tue 2/1011:00 amYYZ - ORD
Nonstop2h 08mUnited Airlines
Deal found 1/6$203
This Mytrip deal was found by Cheapflights users on 1/6. 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 2/38:40 pmORD - YYZ
Nonstop1h 39mAir Canada
Thu 2/56:15 amYYZ - ORD
1 stop5h 51mAir Canada
Deal found 1/6$205
This Mytrip deal was found by Cheapflights users on 1/7. 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.
Wed 2/45:15 amORD - YYZ
1 stop17h 05mMultiple Airlines
Wed 2/118:15 amYYZ - ORD
Nonstop1h 58mMultiple Airlines
Deal found 1/7$206
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Wed 2/118:00 amORD - YYZ
Nonstop1h 40mAir Canada
Sat 2/146:15 amYYZ - ORD
1 stop5h 51mAir Canada
Deal found 1/6$207
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Tue 2/35:32 pmORD - YYZ
1 stop28h 48mMultiple Airlines
Tue 2/107:35 amYYZ - ORD
1 stop15h 33mMultiple Airlines
Deal found 1/6$208
This Mytrip deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:15 amORD - YYZ
1 stop17h 05mMultiple Airlines
Sun 2/812:05 pmYYZ - ORD
Nonstop1h 56mMultiple Airlines
Deal found 1/7$209
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/47:20 amORD - YYZ
1 stop15h 00mMultiple Airlines
Mon 2/97:00 amYYZ - ORD
1 stop29h 22mMultiple Airlines
Deal found 1/6$210
This American Airlines deal was found by Cheapflights users on 1/7. 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.
Tue 2/310:10 amORD - YYZ
1 stop6h 30mAmerican Airlines
Sat 2/74:44 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 1/7$213
This Air Canada deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/510:00 amORD - YYZ
Nonstop1h 40mAir Canada
Thu 2/53:00 pmYYZ - ORD
1 stop6h 10mAir Canada
Deal found 1/6$215
This Kiwi.com deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/57:20 amORD - YYZ
1 stop15h 00mMultiple Airlines
Tue 2/107:35 amYYZ - ORD
1 stop15h 33mMultiple Airlines
Deal found 1/6$216
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/59:41 amORD - YYZ
Nonstop1h 53mAmerican Airlines
Sun 2/84:30 pmYYZ - ORD
1 stop7h 57mAmerican Airlines
Deal found 1/7$218
This Delta deal was found by Cheapflights users on 1/7. 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 2/51:26 pmMDW - YYZ
1 stop8h 16mDelta
Sun 2/86:00 amYYZ - MDW
1 stop3h 52mDelta
Deal found 1/7$237

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 January 8, 2026.
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

Tue 2/17

6:28 pm-9:21 pm

Nonstop1h 53m

Toronto Pearson Intl

Tue 2/24

3:30 pm-4:39 pm

Nonstop2h 09m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 2/7

7:10 am-9:58 am

Nonstop1h 48m

Toronto Pearson Intl

Tue 2/10

3:30 pm-4:40 pm

Nonstop2h 10m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 2/3

9:15 pm-11:59 pm

Nonstop1h 44m

Toronto Pearson Intl

Thu 2/5

3:30 pm-4:40 pm

Nonstop2h 10m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 2/10

7:10 am-9:58 am

Nonstop1h 48m

Toronto Pearson Intl

Tue 2/17

9:00 pm-10:04 pm

Nonstop2h 04m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 2/7

7:10 am-9:58 am

Nonstop1h 48m

Toronto Pearson Intl

Sun 2/8

3:30 pm-4:40 pm

Nonstop2h 10m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 2/3

7:10 am-9:58 am

Nonstop1h 48m

Toronto Pearson Intl

Wed 2/4

3:30 pm-4:28 pm

Nonstop1h 58m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 2/12

1:12 pm-4:02 pm

Nonstop1h 50m

Toronto Pearson Intl

Sun 2/15

9:00 pm-10:04 pm

Nonstop2h 04m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 2/3

9:15 pm-11:59 pm

Nonstop1h 44m

Toronto Pearson Intl

Fri 2/6

9:00 am-10:06 am

Nonstop2h 06m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 2/11

7:10 am-9:58 am

Nonstop1h 48m

Toronto Pearson Intl

Tue 2/17

9:00 pm-10:04 pm

Nonstop2h 04m

$203

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 2/21

7:07 am-9:58 am

Nonstop1h 51m

Toronto Pearson Intl

Sat 2/28

8:45 am-9:50 am

Nonstop2h 05m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 41 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 January 2, 2026.

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, March is the cheapest month in which you can book a flight from Chicago to Hamilton (average of $79). Flying from Chicago to Hamilton in December is currently the most expensive (average of $211). 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 January 8, 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 33% on your trip compared to booking a flight at noon.

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 January 3, 2026.

Travelers seeking maximum savings on their Chicago to Hamilton flight should consider departing on Monday mornings when fares are most often at their lowest. Sunday evenings 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 January 8, 2026.

The most flights from CHI to H4M are scheduled on a Thursday (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 much does it cost to fly round-trip from Chicago to Hamilton?

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 January 8, 2026.
Read through reviews of airlines operating flights from Chicago to Hamilton, such as United Airlines, American Airlines, and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,141 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,141 reviews
United Airlines
7.4
Good
9,141 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
American Airlines
7.2
Good
11,095 reviews
United Airlines
7.4
Good
9,141 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
Air Canada
7.1
Good
10,603 reviews
United Airlines
7.4
Good
9,141 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

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.

  • How long is the flight from Chicago to Hamilton?

    United Airlines and Delta can get you from Chicago to Hamilton in just under 1h 53m. Your travel time can differ by up to 6h 23m. Chicago and Hamilton are separated by a distance of 436 mi. This flight may include one or multiple stops.

  • 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 $64. Users have also found prices from $69 and $74 on United Airlines and American Airlines, respectively.

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

    The top 3 most reliable airlines when flying from Chicago to Hamilton are Korean Air (88%), Royal Jordanian (72%) and Japan Airlines (71%).

  • What are the cheapest flights from Chicago to Hamilton?

    Looking at all options, your cheapest flight can be booked for $96. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $189 on average, our data indicates $1,097 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, March is the cheapest month in which you can book a flight from Chicago to Hamilton (average of $79). Flying from Chicago to Hamilton in December is currently the most expensive (average of $211). 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 Pearson Intl flights
Midway to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Toronto Island flights
Midway to Toronto Island flights
St. Louis to Pearson Intl flights
St. Louis to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Ottawa flights
Midway to Ottawa flights
O'Hare Intl to Hamilton flights
O'Hare Intl to London flights
St. Louis to Ottawa flights
O'Hare Intl to Thunder Bay flights
Moline to Pearson Intl flights
Midway to Thunder Bay flights
Evansville to Pierre Elliott Trudeau Intl flights
Peoria to Pierre Elliott Trudeau Intl flights
Bloomington to Pierre Elliott Trudeau Intl flights
Evansville to Pearson Intl flights
O'Hare Intl to Kingston flights
Bloomington to Ottawa flights
Dubuque to Pearson Intl flights
Springfield to Pearson Intl flights
Champaign 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$117Average$244FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$145Average$293FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$185Average$351FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$215Average$379FlexibilityNo cancel feeOn-time71%

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