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$525+ Cheap flights from Watertown, NY (ART) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
ART — CHI
Sep 6 — Sep 131
Sun 9/6
Sun 9/13
1 adult, Economy
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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 August 7, 2026.

This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/116:00 am -
2 stops13h 05m
Sat 9/1211:51 am -
2 stops9h 59m
Deal found 8/5$542
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/116:00 am -
2 stops13h 05m
Sun 9/138:45 am -
1 stop6h 08m
Deal found 8/5$550
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/104:18 pm -
2 stops17h 45m
Sat 9/126:40 am -
2 stops15h 10m
Deal found 8/5$557
This American Airlines deal was found by Cheapflights users on 8/2. 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 12/226:00 am -
1 stop7h 18m
Sat 12/264:50 pm -
1 stop5h 14m
Deal found 8/2$565
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Tue 10/206:00 am -
1 stop6h 05m
Sun 10/253:37 pm -
1 stop5h 50m
Deal found 8/5$568
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/104:18 pm -
1 stop7h 17m
Mon 9/142:59 pm -
1 stop6h 51m
Deal found 8/5$571
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Tue 9/13:30 pm -
1 stop7h 00m
Mon 9/73:25 pm -
1 stop6h 30m
Deal found 8/3$576
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/104:18 pm -
2 stops14h 41m
Sun 9/133:00 pm -
1 stop6h 50m
Deal found 8/5$580
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/116:00 am -
2 stops13h 05m
Mon 9/1411:51 am -
2 stops9h 59m
Deal found 8/5$589
This American Airlines deal was found by Cheapflights users on 8/5. 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 10/225:25 pm -
2 stops16h 35m
Sun 10/254:50 pm -
1 stop4h 37m
Deal found 8/5$597

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 August 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$542
(American Airlines)

One-way from

$525
(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)
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One-way flight from Watertown to Chicago (CHI)
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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 August 7, 2026.
Use the filters below to find and compare flights from Watertown to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Fri 9/11

6:00 am-6:05 pm

2 stops13h 05m

Chicago O'Hare Intl

Sat 9/12

4:00 pm-10:50 pm

1 stop5h 50m

$547

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Thu 9/10

4:18 pm-9:03 am

2 stops17h 45m

Chicago O'Hare Intl

Sat 9/12

6:40 am-10:50 pm

2 stops15h 10m

$557
Quickest round-trip

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Tue 12/22

6:00 am-12:18 pm

1 stop7h 18m

Chicago O'Hare Intl

Sat 12/26

4:50 pm-11:04 pm

1 stop5h 14m

$565

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Tue 9/1

3:30 pm-9:30 pm

1 stop7h 00m

Chicago O'Hare Intl

Mon 9/7

3:25 pm-10:55 pm

1 stop6h 30m

$576
Cheapest one-way
Quickest one-way

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Sun 8/16

4:00 pm-9:30 pm

1 stop6h 30m

$525

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Mon 8/17

6:00 am-3:15 pm

2 stops10h 15m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

Sorted by cheapest first

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 August.
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 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

No data available for this route at this time. Please check back soon.

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 13h 05m. 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.

See more FAQs

Traveling to a place near Chicago?

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

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