HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Watertown

$337+ Cheap flights from Chicago (CHI) to Watertown, NY (ART)

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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ART
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Watertown 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 Chicago to Watertown

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Watertown (ART). 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 August 14, 2025.

Round-trip from

$337
(American Airlines)
From Chicago (CHI) to Watertown
Search Deals

Find flight deals from Chicago to Watertown

Cheapest flights from Chicago to Watertown
Explore the most affordable flight options available from Chicago to Watertown. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. 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 9/264:45 pmORD - ART
1 stop5h 05mAmerican Airlines
Mon 9/294:27 pmART - ORD
1 stop7h 12mAmerican Airlines
Deal found 8/13$337
This American Airlines deal was found by Cheapflights users on 8/11. 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 8/238:35 amORD - ART
2 stops13h 08mAmerican Airlines
Tue 8/264:09 pmART - ORD
1 stop5h 02mAmerican Airlines
Deal found 8/11$344
This American Airlines deal was found by Cheapflights users on 8/12. 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 8/286:55 amORD - ART
1 stop6h 54mAmerican Airlines
Sun 8/318:25 amART - ORD
1 stop4h 55mAmerican Airlines
Deal found 8/12$481

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Watertown 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 14, 2025.
Use the filters below to find and compare flights from Chicago to Watertown that are best for you.

Fly from

Chicago

Fly to

Watertown

Route

Depart

Return

Price

ChicagoWatertown

ORD - ART

ORDART

Chicago O'Hare Intl

Fri 9/26

4:45 pm-10:50 pm

1 stop5h 05m

Watertown

Mon 9/29

4:27 pm-10:39 pm

1 stop7h 12m

$337

ChicagoWatertown

ORD - ART

ORDART

Chicago O'Hare Intl

Thu 8/28

6:55 am-2:49 pm

1 stop6h 54m

Watertown

Sun 8/31

8:25 am-12:20 pm

1 stop4h 55m

$481

ChicagoWatertown

ORD - ART

ORDART

Chicago O'Hare Intl

Mon 9/15

8:00 am-10:50 pm

2 stops13h 50m

Watertown

Wed 9/17

6:00 am-5:54 pm

2 stops12h 54m

$602

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Best time to book a flight from Chicago to Watertown

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

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Watertown, New York (average of $187). Flying from Chicago to Watertown, New York in May is currently the most expensive (average of $423). 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 Chicago to Watertown. 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 into for flights to Watertown from Chicago?

    For a flight from Chicago to Watertown, you will be flying into Watertown. Watertown (ART) is just 5.6 mi from the center of the city. Watertown is the only Watertown airport and it handles 0 inbound flights from Chicago per day. 0 airlines have flights to Watertown from Chicago on a regular basis.

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

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

  • How can I find direct flights from Chicago to Watertown?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Watertown 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 Watertown, New York?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Watertown, New York (average of $187). Flying from Chicago to Watertown, New York in May is currently the most expensive (average of $423). 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 Watertown?

Book flights to Watertown if you plan to visit one of these locations
Alexandria Bay

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 Watertown

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