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$244+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
ART — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$244
(American Airlines)
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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 9/254:27 pmART - ORD
2 stops8h 21mAmerican Airlines
Mon 9/298:35 amORD - ART
1 stop6h 27mAmerican Airlines
Deal found 9/10$244
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 9/264:27 pmART - ORD
2 stops7h 45mAmerican Airlines
Tue 9/307:10 amORD - ART
2 stops7h 52mAmerican Airlines
Deal found 9/11$249
This American Airlines deal was found by Cheapflights users on 9/11. 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 9/278:00 amART - ORD
1 stop5h 20mAmerican Airlines
Sun 9/289:48 amORD - ART
1 stop5h 14mAmerican Airlines
Deal found 9/11$308
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 9/256:00 amART - ORD
2 stops10h 50mAmerican Airlines
Sat 9/279:48 amORD - ART
1 stop5h 14mAmerican Airlines
Deal found 9/11$314
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 9/256:00 amART - ORD
2 stops10h 50mAmerican Airlines
Sun 9/285:00 amORD - ART
2 stops10h 02mAmerican Airlines
Deal found 9/11$319
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 9/234:27 pmART - ORD
1 stop5h 16mAmerican Airlines
Sat 9/279:48 amORD - ART
1 stop5h 14mAmerican Airlines
Deal found 9/11$338
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 9/236:00 amART - ORD
2 stops8h 24mAmerican Airlines
Sun 9/285:00 amORD - ART
2 stops10h 02mAmerican Airlines
Deal found 9/11$349
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 10/102:45 pmART - ORD
1 stop6h 26mAmerican Airlines
Tue 10/146:45 amORD - ART
1 stop6h 14mAmerican Airlines
Deal found 9/9$445
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 9/264:27 pmART - ORD
1 stop5h 16mAmerican Airlines
Sun 9/289:48 amORD - ART
1 stop5h 14mAmerican Airlines
Deal found 9/11$448

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 September 11, 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 9/25

4:27 pm-11:48 pm

2 stops8h 21m

Chicago O'Hare Intl

Mon 9/29

8:35 am-4:02 pm

1 stop6h 27m

$244

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 9/26

4:27 pm-11:12 pm

2 stops7h 45m

Chicago O'Hare Intl

Tue 9/30

7:10 am-4:02 pm

2 stops7h 52m

$249

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 9/26

4:27 pm-11:48 pm

2 stops8h 21m

Chicago O'Hare Intl

Sat 9/27

8:35 am-4:02 pm

1 stop6h 27m

$314

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 9/25

6:00 am-3:50 pm

2 stops10h 50m

Chicago O'Hare Intl

Sat 9/27

9:48 am-4:02 pm

1 stop5h 14m

$314

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 9/27

4:27 pm-11:48 pm

2 stops8h 21m

Chicago O'Hare Intl

Sun 9/28

9:48 am-4:02 pm

1 stop5h 14m

$314

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 9/25

6:00 am-3:50 pm

2 stops10h 50m

Chicago O'Hare Intl

Sun 9/28

5:00 am-4:02 pm

2 stops10h 02m

$319

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 9/23

6:00 am-12:20 pm

1 stop7h 20m

Chicago O'Hare Intl

Sun 9/28

9:48 am-4:02 pm

1 stop5h 14m

$338

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 9/24

6:00 am-12:20 pm

1 stop7h 20m

Chicago O'Hare Intl

Sat 9/27

9:48 am-4:02 pm

1 stop5h 14m

$338

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 9/23

6:00 am-1:42 pm

2 stops8h 42m

Chicago O'Hare Intl

Sat 9/27

8:35 am-4:02 pm

1 stop6h 27m

$344

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 10/10

6:00 am-1:43 pm

2 stops8h 43m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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, August is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $245). Flying from Watertown, New York to Chicago in March is currently the most expensive (average of $321). 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 8h 21m. 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, August is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $245). Flying from Watertown, New York to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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