HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hamilton

$70+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 June or July, booked 68 days in advance, depart on a Thursday or Friday and return on a Saturday

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 August 21, 2025.

Round-trip from

$167
(United Airlines)

One-way from

$70
(Mytrip)

Popular in

December

Cheapest in

June

Average price

$305
From Chicago (CHI) to Hamilton
Search Deals
One-way flight from Chicago (CHI) to Hamilton
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($23 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 August 2025
Search Deals

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 August 21, 2025.

This United Airlines deal was found by Cheapflights users on 8/21. 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 11/79:20 pmORD - YYZ
Nonstop1h 39mUnited Airlines
Sun 11/99:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 8/21$167
This Gotogate deal was found by Cheapflights users on 8/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/243:50 pmORD - YYZ
Nonstop1h 43mAir Canada
Mon 10/272:15 pmYYZ - ORD
Nonstop1h 55mAir Canada
Deal found 8/19$168
This Flightnetwork deal was found by Cheapflights users on 8/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:55 amORD - YYZ
Nonstop1h 43mAir Canada
Sun 10/58:20 amYYZ - ORD
Nonstop1h 54mAir Canada
Deal found 8/19$169
This United Airlines deal was found by Cheapflights users on 8/21. 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 11/72:00 pmORD - YYZ
1 stop8h 46mUnited Airlines
Mon 11/106:52 amYYZ - ORD
Nonstop2h 06mUnited Airlines
Deal found 8/21$177
This Delta deal was found by Cheapflights users on 8/21. 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 10/29:35 amMDW - YYZ
1 stop6h 48mDelta
Sun 10/512:14 pmYYZ - MDW
1 stop7h 21mDelta
Deal found 8/21$233
This Delta deal was found by Cheapflights users on 8/19. 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 9/206:15 pmMDW - YYZ
1 stop3h 41mDelta
Tue 9/236:00 amYYZ - MDW
1 stop8h 03mDelta
Deal found 8/19$268
This Delta deal was found by Cheapflights users on 8/20. 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.
Fri 10/109:35 amMDW - YYZ
1 stop6h 44mDelta
Wed 10/1512:15 pmYYZ - MDW
1 stop7h 10mDelta
Deal found 8/20$283
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/49:20 amMDW - YYZ
1 stop13h 00mWestJet
Sat 10/118:00 amYYZ - MDW
2 stops10h 43mWestJet
Deal found 8/20$292
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Sat 9/2011:00 amMDW - YYZ
1 stop9h 51mWestJet
Mon 9/228:00 pmYYZ - MDW
2 stops14h 40mWestJet
Deal found 8/21$293
This Delta deal was found by Cheapflights users on 8/19. 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 9/199:29 amMDW - YYZ
1 stop6h 54mDelta
Mon 9/2212:15 pmYYZ - MDW
1 stop7h 20mDelta
Deal found 8/19$300
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:21 amMDW - YYZ
1 stop14h 00mMultiple Airlines
Sun 9/288:00 pmYYZ - MDW
1 stop12h 23mMultiple Airlines
Deal found 8/19$307
This SmartFares deal was found by Cheapflights users on 8/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/201:43 pmMDW - YYZ
1 stop8h 37mWestJet
Sat 9/271:20 pmYYZ - MDW
1 stop8h 50mWestJet
Deal found 8/19$310

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 August 21, 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

Sat 11/15

9:20 pm-11:59 pm

Nonstop1h 39m

Toronto Pearson Intl

Mon 11/17

5:30 pm-6:39 pm

Nonstop2h 09m

$167

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 11/15

3:55 pm-6:34 pm

Nonstop1h 39m

Toronto Pearson Intl

Sun 11/16

4:30 pm-5:28 pm

Nonstop1h 58m

$167

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 11/7

9:20 pm-11:59 pm

Nonstop1h 39m

Toronto Pearson Intl

Sun 11/9

9:00 pm-10:05 pm

Nonstop2h 05m

$167

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 11/2

1:19 pm-4:02 pm

Nonstop1h 43m

Toronto Pearson Intl

Thu 11/20

7:40 pm-11:43 pm

1 stop5h 03m

$167

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 10/2

8:25 pm-11:08 pm

Nonstop1h 43m

Toronto Pearson Intl

Sun 10/5

8:20 am-9:14 am

Nonstop1h 54m

$171

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 10/5

9:55 am-12:38 pm

Nonstop1h 43m

Toronto Pearson Intl

Sun 10/12

8:20 am-9:14 am

Nonstop1h 54m

$172

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 10/4

9:55 am-12:38 pm

Nonstop1h 43m

Toronto Pearson Intl

Sat 10/11

2:10 pm-3:04 pm

Nonstop1h 54m

$172

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 11/19

7:15 am-1:43 pm

1 stop5h 28m

Toronto Pearson Intl

Sun 11/23

6:52 am-7:57 am

Nonstop2h 05m

$177

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 10/2

9:35 am-5:23 pm

1 stop6h 48m

Toronto Pearson Intl

Sun 10/5

12:14 pm-6:35 pm

1 stop7h 21m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 10/29

9:35 am-2:45 pm

1 stop4h 10m

Toronto Pearson Intl

Sat 11/1

6:15 am-12:31 pm

1 stop7h 16m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 34 results
1
2
3
4

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 August 8, 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 August is currently the most expensive (average of $348). 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 August 21, 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 August 17, 2025.

Travelers seeking maximum savings on their Chicago to Hamilton flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon 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 August 21, 2025.

The most flights from CHI to H4M are scheduled on a Wednesday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (49 on average).

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 August 21, 2025.
Read through reviews of airlines operating flights from Chicago to Hamilton, such as Porter Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
341 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
7.9
Good
341 reviews
Porter Airlines
7.9
Good
341 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,930 reviews
Porter Airlines
7.9
Good
341 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
7.9
Good
341 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
341 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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, Air Canada, and Delta can get you from Chicago to Hamilton in just under 1h 39m. Your travel time can differ by up to 5h 09m. 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 SkyWest Airlines (86%), Japan Airlines (82%) and Envoy Air (80%).

  • 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 $156 on average our data indicates $907 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 August is currently the most expensive (average of $348). 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

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.

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 Pierre Elliott Trudeau Intl flights
St. Louis to Pearson Intl flights
O'Hare Intl to Ottawa 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
Midway to Thunder Bay flights
O'Hare Intl to Thunder Bay flights
Peoria to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Kingston flights
Bloomington to Ottawa flights
Evansville to Pierre Elliott Trudeau Intl flights
Dubuque to Pearson Intl flights
Springfield to Pearson Intl flights
Champaign to Pearson Intl flights
Bloomington to Pierre Elliott Trudeau 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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$120Average$275FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$145Average$313FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$187Average$266FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$218Average$388FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.