How long is the flight from Watertown, New York to Chicago?

There are many flights that can get you from Watertown, New York to Chicago in 6h 45m. Fly via American Airlines to get the fastest option. The distance between Watertown, New York and Chicago is about 615 mi.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest time of day to fly from ART to CHI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Watertown, New York to Chicago as you normally would.

Most accurate provider : When it comes to deals on Watertown, New York-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Watertown, New York-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Watertown, New York-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Watertown, New York-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Watertown, New York-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly from for flights from Watertown to Chicago?

Most people fly from Watertown (ART) if they book a flight from Watertown to Chicago. On average, Watertown has 0 outbound flights to Chicago per day from 0 airlines. Watertown is conveniently located just 5.6 mi from Watertown’s city center.

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

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

How can I find direct flights from Watertown to Chicago?

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

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

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

$238+ Flights from Watertown, NY to Chicago

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Cheap flight deals from Watertown to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$238 (American Airlines)

Provider with most accurate pricing for Watertown-Chicago (CHI) flight deals.

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Provider most trusted by Cheapflights users for Watertown-Chicago (CHI) flights.

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From Watertown to Chicago (CHI)

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Find flight deals from Watertown to Chicago

Cheapest flights from Watertown to Chicago
Explore the most affordable flight options available from Watertown to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2025.

Tue 10/288:30 amART - ORD

1 stop6h 41mAmerican Airlines

Sat 11/18:45 amORD - ART

1 stop5h 58mAmerican Airlines

Deal found 10/13

$238

Sun 10/266:00 amART - ORD

1 stop5h 43mAmerican Airlines

Thu 10/304:52 pmORD - ART

1 stop5h 04mAmerican Airlines

Deal found 10/11

$920

Best flights from Watertown to Chicago
Discover carefully curated flight deals from Watertown to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2025.

Tue 10/282:26 pmART - ORD

1 stop6h 45mAmerican Airlines

Sat 11/15:20 amORD - ART

2 stops9h 23mAmerican Airlines

Deal found 10/13

$244

Wed 4/86:24 amART - ORD

1 stop6h 52mAmerican Airlines

Sat 4/116:45 amORD - ART

1 stop4h 15mAmerican Airlines

Deal found 10/10

$514

Sun 10/266:00 amART - ORD

1 stop5h 43mAmerican Airlines

Thu 10/304:52 pmORD - ART

1 stop5h 04mAmerican Airlines

Deal found 10/11

$920

Last-minute flights from Watertown to Chicago
Discover last-minute flight deals from Watertown to Chicago. Data last updated October 13, 2025 and is based on user searches.

Sun 10/266:00 amART - ORD

1 stop5h 43mAmerican Airlines

Thu 10/304:52 pmORD - ART

1 stop5h 04mAmerican Airlines

Deal found 10/11

$920

Tue 10/288:30 amART - ORD

1 stop6h 41mAmerican Airlines

Sat 11/18:45 amORD - ART

1 stop5h 58mAmerican Airlines

Deal found 10/13

$238

One-way flights from Watertown to Chicago
Search for one-way flight options from Watertown to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2025.

Thu 11/132:33 pmART - ORD

1 stop6h 58mAmerican Airlines

Deal found 10/12

$460

Fly from

Fly to

Route

Depart

Return

Price

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 10/28

2:26 pm-8:11 pm

1 stop6h 45m

Chicago O'Hare Intl

Sat 11/1

5:20 am-3:43 pm

2 stops9h 23m

$244

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 4/8

6:24 am-12:16 pm

1 stop6h 52m

Chicago O'Hare Intl

Sat 4/11

6:45 am-12:00 pm

1 stop4h 15m

$514

WatertownChicago

ART - ORD

ARTORD

Watertown

Sun 10/26

6:00 am-10:43 am

1 stop5h 43m

Chicago O'Hare Intl

Thu 10/30

4:52 pm-10:56 pm

1 stop5h 04m

$920

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 11/13

2:33 pm-8:31 pm

1 stop6h 58m

$460

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Compare providers for flights from Watertown to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Watertown to Chicago in October.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Expedia	Price Accuracy2 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Watertown, New York-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Watertown, New York-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Watertown, New York-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Watertown, New York-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Watertown, New York-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Watertown to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Watertown 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 Watertown to Chicago

What is the cheapest month to book a flight from Watertown, New York to Chicago?

Currently, December is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $121). Flying from Watertown, New York to Chicago in July is currently the most expensive (average of $271). 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.

Related info for your journey

What airport do you fly from for flights from Watertown to Chicago?
Most people fly from Watertown (ART) if they book a flight from Watertown to Chicago. On average, Watertown has 0 outbound flights to Chicago per day from 0 airlines. Watertown is conveniently located just 5.6 mi from Watertown’s city center.
How long is the flight from Watertown, New York to Chicago?
There are many flights that can get you from Watertown, New York to Chicago in 6h 45m. Fly via American Airlines to get the fastest option. The distance between Watertown, New York and Chicago is about 615 mi.
Can I find deals for flights from Watertown to Chicago that include hotel bookings?
Yes. In addition to deals on Watertown to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Watertown to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Watertown to Chicago.
Can I find deals for business class flights from Watertown to Chicago?
Yes. Cheapflights offers flight deals from Watertown to Chicago 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 Watertown, New York to Chicago?
Currently, December is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $121). Flying from Watertown, New York to Chicago in July is currently the most expensive (average of $271). 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.

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$238+ Cheap flights from Watertown, NY (ART) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Watertown to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Watertown to Chicago

Most accurate provider

Most trusted provider

Round-trip from

Find flight deals from Watertown to Chicago

Cheapest flights from Watertown to ChicagoExplore the most affordable flight options available from Watertown to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2025.

Explore the most affordable flight options available from Watertown to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Watertown to Chicago that are best for you.

Compare providers for flights from Watertown to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Watertown to Chicago in October.

Best time to book a flight from Watertown to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Watertown with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Watertown to Chicago

What is the cheapest month to book a flight from Watertown, New York to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Watertown to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Watertown to Chicago?

How long is the flight from Watertown, New York to Chicago?

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

How can I find direct flights from Watertown to Chicago?

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

What is the cheapest month to book a flight from Watertown, New York to Chicago?

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Cheapest flights from Watertown to Chicago
Explore the most affordable flight options available from Watertown to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2025.