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Watertown

$658+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ART
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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Cheap 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 March 10, 2026.

This American Airlines deal was found by Cheapflights users on 3/8. 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.
Fri 6/198:32 am
ORD
-
ART
1 stop6h 07m
American Airlines
Mon 6/224:06 pm
ART
-
ORD
1 stop6h 30m
American Airlines
Deal found 3/8$658
This KAYAK deal was found by Cheapflights users on 3/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/164:48 pm
ORD
-
ART
1 stop5h 07m
American Airlines
Fri 3/204:01 pm
ART
-
ORD
1 stop21h 01m
American Airlines
Deal found 3/10$869
This KAYAK deal was found by Cheapflights users on 3/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/188:23 am
ORD
-
ART
1 stop5h 56m
American Airlines
Fri 3/206:00 am
ART
-
ORD
1 stop5h 12m
American Airlines
Deal found 3/6$953
This American Airlines deal was found by Cheapflights users on 3/9. 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.
Mon 3/231:39 pm
ORD
-
ART
2 stops8h 16m
American Airlines
Wed 3/254:01 pm
ART
-
ORD
1 stop6h 17m
American Airlines
Deal found 3/9$959

Find 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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$658
(American Airlines)
Provider with most accurate pricing for Chicago (CHI)-Watertown flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Watertown flights.
Search Deals
From Chicago (CHI) to Watertown
Search Deals

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 March 10, 2026.
Use the filters below to find and compare flights from Chicago to Watertown that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWatertown

ORD - ART

ORDART

Chicago O'Hare Intl

Fri 6/19

8:32 am-3:39 pm

1 stop6h 07m

Watertown

Mon 6/22

4:06 pm-9:36 pm

1 stop6h 30m

$658
Quickest round-trip

ChicagoWatertown

ORD - ART

ORDART

Chicago O'Hare Intl

Mon 3/23

4:48 pm-10:55 pm

1 stop5h 07m

Watertown

Wed 3/25

4:01 pm-9:18 pm

1 stop6h 17m

$953

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Sorted by cheapest first

Compare providers for flights from Chicago to Watertown

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 Chicago to Watertown in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 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 Chicago-Watertown, New York flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Watertown, New York flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Watertown, New York flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Watertown, New York 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 Chicago-Watertown, New York 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 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, August is the cheapest month in which you can book a flight from Chicago to Watertown, New York (average of $200). Flying from Chicago to Watertown, New York in April is currently the most expensive (average of $257). 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.

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

    Departing from Chicago to Watertown, New York will take you 5h 56m. The distance between Chicago and Watertown, New York is about 615 mi.

  • 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, August is the cheapest month in which you can book a flight from Chicago to Watertown, New York (average of $200). Flying from Chicago to Watertown, New York in April is currently the most expensive (average of $257). 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?

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