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$86+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Hamilton are usually found in June or July, booked 68 days in advance, depart on a Thursday or Friday and return on a Saturday

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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/67:10 amORD - YYZ
1 stop10h 18mAmerican Airlines
Sun 12/76:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Deal found 10/28$194
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 12/59:39 amORD - YYZ
Nonstop1h 51mAmerican Airlines
Sun 12/76:00 amYYZ - ORD
1 stop6h 03mAmerican Airlines
Deal found 10/28$200
This Flightnetwork deal was found by Cheapflights users on 10/29. 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.
Fri 12/58:15 pmORD - YYZ
Nonstop1h 39mAir Canada
Sun 12/77:00 amYYZ - ORD
1 stop5h 18mAir Canada
Deal found 10/29$203
This Flightnetwork deal was found by Cheapflights users on 10/29. 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.
Thu 12/48:00 amORD - YYZ
Nonstop1h 40mAir Canada
Sun 12/77:00 amYYZ - ORD
1 stop5h 18mAir Canada
Deal found 10/29$204
This Booking.com deal was found by Cheapflights users on 10/28. 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.
Mon 12/810:00 amORD - YYZ
Nonstop1h 40mAir Canada
Thu 12/116:30 pmYYZ - ORD
Nonstop2h 00mAir Canada
Deal found 10/28$206
This Mytrip deal was found by Cheapflights users on 10/29. 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 11/268:00 amORD - YYZ
Nonstop1h 40mAir Canada
Fri 11/282:15 pmYYZ - ORD
Nonstop1h 55mAir Canada
Deal found 10/29$208
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/265:00 amORD - YYZ
1 stop5h 03mAmerican Airlines
Tue 12/211:59 amYYZ - ORD
1 stop4h 57mAmerican Airlines
Deal found 10/28$209
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/157:10 amORD - YYZ
Nonstop1h 48mUnited Airlines
Wed 1/149:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 10/28$210
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 12/58:10 amORD - YYZ
Nonstop1h 46mAmerican Airlines
Mon 12/811:36 amYYZ - ORD
Nonstop1h 55mAmerican Airlines
Deal found 10/28$212
This Delta deal was found by Cheapflights users on 10/28. 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 12/59:34 amMDW - YYZ
1 stop4h 14mDelta
Sun 12/712:13 pmYYZ - MDW
1 stop6h 47mDelta
Deal found 10/28$233
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Mon 12/153:10 pmMDW - YYZ
1 stop8h 01mMultiple Airlines
Thu 1/157:10 amYYZ - MDW
1 stop14h 35mMultiple Airlines
Deal found 10/28$243
This Delta deal was found by Cheapflights users on 10/28. 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 12/156:40 pmMDW - YYZ
1 stop3h 31mDelta
Wed 1/1410:05 amYYZ - MDW
1 stop8h 29mDelta
Deal found 10/28$250

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 October 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$192
(Air Canada)

One-way from

$86
(American Airlines)

Popular in

December

Cheapest in

June

Average price

$295
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
Search Deals
From Chicago (CHI) to Hamilton
Search Deals
One-way flight from Chicago (CHI) to Hamilton
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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

Mon 12/15

7:10 am-9:58 am

Nonstop1h 48m

Toronto Pearson Intl

Sat 1/17

8:55 am-10:01 am

Nonstop2h 06m

$210

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 12/17

4:50 pm-7:45 pm

Nonstop1h 55m

Toronto Pearson Intl

Sat 1/17

3:30 pm-4:40 pm

Nonstop2h 10m

$210

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 12/15

9:10 pm-11:59 pm

Nonstop1h 49m

Toronto Pearson Intl

Fri 1/16

9:00 pm-10:05 pm

Nonstop2h 05m

$210

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 12/16

8:45 am-2:14 pm

1 stop4h 29m

Toronto Pearson Intl

Sat 1/17

8:55 am-10:01 am

Nonstop2h 06m

$220

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 12/17

8:45 am-2:14 pm

1 stop4h 29m

Toronto Pearson Intl

Tue 1/13

5:30 pm-6:50 pm

Nonstop2h 20m

$220

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 1/8

8:52 am-2:14 pm

1 stop4h 22m

Toronto Pearson Intl

Mon 1/12

9:00 pm-10:05 pm

Nonstop2h 05m

$220

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 1/19

1:58 pm-7:08 pm

1 stop4h 10m

Toronto Pearson Intl

Wed 1/21

10:05 am-1:18 pm

1 stop4h 13m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 1/20

6:50 am-11:20 am

1 stop3h 30m

Toronto Pearson Intl

Wed 1/21

12:12 pm-4:56 pm

1 stop5h 44m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 1/14

1:54 pm-7:13 pm

1 stop4h 19m

Toronto Pearson Intl

Wed 1/21

6:00 am-9:40 am

1 stop4h 40m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 1/14

1:54 pm-7:13 pm

1 stop4h 19m

Toronto Pearson Intl

Fri 1/16

10:05 am-1:07 pm

1 stop4h 02m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 42 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 October 24, 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, March is the cheapest month in which you can book a flight from Chicago to Hamilton (average of $106). Flying from Chicago to Hamilton in July is currently the most expensive (average of $173). 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Hamilton in the evening. If you’re flexible enough to do this you can expect to save up to 25% 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 October 26, 2025.

Travelers seeking maximum savings on their Chicago to Hamilton flight should consider departing on Wednesday afternoons 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.

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 October 30, 2025.
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
8,998 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,030 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,376 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 48m. Your travel time can differ by up to 3h 21m. Chicago and Hamilton are separated by a distance of 436 mi. This flight may include one or multiple stops.

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

    The top 3 most reliable airlines when flying from Chicago to Hamilton are Finnair (92%), Qatar Airways (91%) and British Airways (89%).

  • What are the cheapest flights from Chicago to Hamilton?

    Looking at all options, your cheapest flight can be booked for $122. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $166 on average, our data indicates $826 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 $106). Flying from Chicago to Hamilton in July is currently the most expensive (average of $173). 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 Toronto Island flights
Midway to Pearson Intl flights
O'Hare Intl to Toronto Island flights
Midway to Pierre Elliott Trudeau Intl flights
St. Louis to Pearson Intl flights
O'Hare Intl to Ottawa flights
St. Louis to Pierre Elliott Trudeau Intl flights
Midway to Ottawa flights
St. Louis to Ottawa flights
Moline to Pearson Intl flights
O'Hare Intl to Hamilton flights
O'Hare Intl to London flights
Evansville to Pierre Elliott Trudeau Intl flights
Evansville to Pearson Intl flights
O'Hare Intl to Thunder Bay flights
Midway to Thunder Bay flights
Peoria to Pierre Elliott Trudeau Intl flights
Bloomington to Pierre Elliott Trudeau Intl flights
Dubuque to Pearson Intl flights
Bloomington to Ottawa flights
O'Hare Intl to Kingston 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$109Average$270FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$118Average$264FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$146Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$223Average$388FlexibilityNo cancel feeOn-time71%

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