HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$351+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
ART — CHI
Jan 9 — Jan 161
Fri 1/9
Fri 1/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Watertown to Chicago 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.

Cheap 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 December 10, 2025.

This American Airlines deal was found by Cheapflights users on 12/10. 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 12/122:30 pmART - ORD
1 stop7h 04mAmerican Airlines
Sun 12/148:29 amORD - ART
1 stop4h 36mAmerican Airlines
Deal found 12/10$558
This American Airlines deal was found by Cheapflights users on 12/8. 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 12/236:00 amART - ORD
1 stop5h 03mAmerican Airlines
Sat 12/274:51 pmORD - ART
1 stop5h 13mAmerican Airlines
Deal found 12/8$644

Find flight deals from Watertown to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Watertown (ART) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$351
(American Airlines)
Provider with most accurate pricing for Watertown-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Watertown-Chicago (CHI) flights.
Search Deals
From Watertown to Chicago (CHI)
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Watertown to Chicago 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 December 10, 2025.
Use the filters below to find and compare flights from Watertown to Chicago that are best for you.

Fly from

Watertown

Fly to

Chicago

Route

Depart

Return

Price

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/5

6:00 am-10:11 am

1 stop5h 11m

Chicago O'Hare Intl

Sun 3/8

2:20 pm-10:55 pm

1 stop7h 35m

$351

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 12/23

6:00 am-10:03 am

1 stop5h 03m

Chicago O'Hare Intl

Sat 12/27

4:51 pm-11:04 pm

1 stop5h 13m

$644

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 12/19

6:00 am-10:03 am

1 stop5h 03m

$726

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Watertown, New York-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, February is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $144). 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

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?

    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 5h 11m. 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, February is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $144). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 Watertown to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
LaGuardia to Midway flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
John F Kennedy Intl to St. Louis flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
Buffalo to O'Hare Intl flights
Albany to O'Hare Intl flights
Syracuse to O'Hare Intl flights
Buffalo to Midway flights
Rochester to O'Hare Intl flights
White Plains to O'Hare Intl flights
Albany to Midway flights
Syracuse to Midway flights
Islip to O'Hare Intl flights
Stewart to O'Hare Intl flights
Rochester to Midway flights
White Plains to Midway flights
John F Kennedy Intl to Moline flights
Syracuse to St. Louis flights
Albany to St. Louis flights
Newark to Moline flights
Stewart to St. Louis flights
Ithaca to O'Hare Intl flights
Stewart to Rockford flights
LaGuardia to Moline flights
LaGuardia to Peoria flights
White Plains to St. Louis flights
LaGuardia to Decatur flights
Elmira to O'Hare Intl flights
Elmira to Midway flights
Newark to Peoria flights
Buffalo to St. Louis flights
Islip to St. Louis flights
Rochester to St. Louis flights
Binghamton to O'Hare Intl flights
Newark to Bloomington flights
John F Kennedy Intl to Bloomington flights
LaGuardia to Bloomington flights
Buffalo to Moline flights
John F Kennedy Intl to Peoria flights
LaGuardia to Evansville flights
Ithaca to St. Louis flights
Albany to Moline flights
Albany to Peoria flights
Binghamton to Midway flights

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.