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$258+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
ART — CHI
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Cheap 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 November 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$258
(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 November 5, 2025.

This American Airlines deal was found by Cheapflights users on 11/3. 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.
Wed 11/196:00 amART - ORD
1 stop5h 25mAmerican Airlines
Sun 11/236:47 amORD - ART
1 stop6h 21mAmerican Airlines
Deal found 11/3$258
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/206:00 amART - ORD
2 stops9h 14mAmerican Airlines
Mon 11/246:47 amORD - ART
1 stop6h 21mAmerican Airlines
Deal found 11/5$383

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 November 5, 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 11/20

6:00 am-12:28 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 11/24

6:47 am-2:08 pm

1 stop6h 21m

$258

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 11/19

6:00 am-10:25 am

1 stop5h 25m

Chicago O'Hare Intl

Sun 11/23

6:47 am-2:08 pm

1 stop6h 21m

$258

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/5

6:00 am-10:10 am

1 stop5h 10m

Chicago O'Hare Intl

Sun 3/8

2:36 pm-10:20 pm

1 stop6h 44m

$441

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 4/8

6:24 am-11:08 am

1 stop5h 44m

Chicago O'Hare Intl

Sat 4/11

6:45 am-12:00 pm

1 stop4h 15m

$542

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 11/18

6:00 am-10:25 am

1 stop5h 25m

$433

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

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 November.
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 7h 28m. 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
Hammond
Porter
Benton Harbor
Merrillville

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