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$238+ Cheap flights from Watertown, NY (ART) to Illinois

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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
ART — ORD
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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Cheap flight deals from Watertown to Illinois

Keep the following information in mind while searching for Watertown to Illinois flight deals. Data was last updated October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(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 Illinois
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Find flight deals from Watertown to Illinois

Cheapest flights from Watertown to Illinois
Explore the most affordable flight options available from Watertown to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.

This American Airlines deal was found by Cheapflights users on 10/20. 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 11/46:00 amART - ORD
1 stop7h 30mAmerican Airlines
Sat 11/86:50 amORD - ART
1 stop6h 18mAmerican Airlines
Deal found 10/20$238
This American Airlines deal was found by Cheapflights users on 10/20. 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
1 stop5h 25mAmerican Airlines
Sun 11/236:47 amORD - ART
1 stop6h 21mAmerican Airlines
Deal found 10/20$337
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/52:33 pmART - ORD
1 stop6h 53mAmerican Airlines
Sun 11/98:30 amORD - ART
1 stop4h 38mAmerican Airlines
Deal found 10/21$449
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/216:00 amART - ORD
2 stops9h 14mAmerican Airlines
Sun 11/236:47 amORD - ART
1 stop6h 21mAmerican Airlines
Deal found 10/20$543
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/196:00 amART - ORD
1 stop6h 59mAmerican Airlines
Fri 12/2611:07 amORD - ART
1 stop6h 23mAmerican Airlines
Deal found 10/20$652

Cheapflights Fare Finder

 
Customize your flight search to find flights from Watertown to Illinois 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 October 22, 2025.
Use the filters below to find and compare flights from Watertown to Illinois that are best for you.

Fly from

Watertown

Fly to

Illinois

Route

Depart

Return

Price

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 11/4

6:00 am-12:30 pm

1 stop7h 30m

Chicago O'Hare Intl

Sat 11/8

6:50 am-2:08 pm

1 stop6h 18m

$238

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 2/20

4:30 pm-8:09 pm

1 stop4h 39m

Chicago O'Hare Intl

Tue 2/24

9:45 am-2:55 pm

1 stop4h 10m

$288

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 2/18

4:30 pm-9:54 pm

2 stops6h 24m

Chicago O'Hare Intl

Tue 2/24

2:55 pm-10:23 pm

1 stop6h 28m

$294

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 11/21

2:33 pm-8:26 pm

1 stop6h 53m

Chicago O'Hare Intl

Sun 11/23

6:47 am-2:08 pm

1 stop6h 21m

$337

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 11/20

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

$337

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/5

4:30 pm-8:09 pm

1 stop4h 39m

Chicago O'Hare Intl

Sun 3/8

9:45 am-2:55 pm

1 stop4h 10m

$407

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 2/20

4:30 pm-8:09 pm

1 stop4h 39m

Chicago O'Hare Intl

Mon 2/23

11:52 am-10:23 pm

2 stops9h 31m

$418

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 2/18

4:30 pm-10:45 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 2/23

11:52 am-10:23 pm

2 stops9h 31m

$418

WatertownSt. Louis

ART - STL

ARTSTL

Watertown

Sat 4/4

4:37 pm-10:18 pm

2 stops6h 41m

Lambert-St Louis

Tue 4/7

12:56 pm-10:29 pm

2 stops8h 33m

$591

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Best time to book a flight from Watertown to Illinois

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

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

Currently, December is the cheapest month in which you can book a flight from Watertown, New York to Illinois (average of $125). Flying from Watertown, New York to Illinois 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 Illinois. 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 Illinois?

    Located just 5.6 mi from the city center, Watertown (ART) is the airport most travelers will use when flying to Illinois from Watertown.

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

    There are many flights that can get you from Watertown, New York to Illinois in 7h 30m. Fly via American Airlines to get the fastest option. The distance from Watertown, New York to Illinois is about 615 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Watertown to Illinois 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 Illinois?

    Currently, December is the cheapest month in which you can book a flight from Watertown, New York to Illinois (average of $125). Flying from Watertown, New York to Illinois 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

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