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$258+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
ART — ORD
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Watertown to Illinois

Best flights from Watertown to Illinois
Discover carefully curated flight deals from Watertown to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/22. 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 1/67:00 amART - ORD
1 stop6h 27mAmerican Airlines
Sat 1/1011:49 amORD - ART
1 stop5h 25mAmerican Airlines
Deal found 12/22$258
This American Airlines deal was found by Cheapflights users on 12/22. 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 1/197:00 amART - ORD
1 stop7h 59mAmerican Airlines
Mon 1/269:54 amORD - ART
1 stop7h 20mAmerican Airlines
Deal found 12/22$357
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 1/56:00 amART - ORD
1 stop5h 03mAmerican Airlines
Fri 1/92:50 pmORD - ART
1 stop5h 33mAmerican Airlines
Deal found 12/21$1,077

Find flight deals from Watertown to Illinois

Keep the following information in mind while searching for Watertown to Illinois flight deals. Data was last updated December 23, 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.
Search Deals
Provider most trusted by Cheapflights users for Watertown-Chicago (CHI) flights.
Search Deals
From Watertown to Illinois
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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 December 23, 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 1/6

7:00 am-12:27 pm

1 stop6h 27m

Chicago O'Hare Intl

Sat 1/10

11:49 am-6:14 pm

1 stop5h 25m

$258

WatertownChicago

ART - ORD

ARTORD

Watertown

Mon 1/19

7:00 am-1:59 pm

1 stop7h 59m

Chicago O'Hare Intl

Mon 1/26

9:54 am-6:14 pm

1 stop7h 20m

$357

WatertownChicago

ART - ORD

ARTORD

Watertown

Mon 1/5

6:00 am-10:03 am

1 stop5h 03m

Chicago O'Hare Intl

Fri 1/9

2:50 pm-9:23 pm

1 stop5h 33m

$1,077

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 12/30

6:00 am-10:03 am

1 stop5h 03m

$433

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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, February is the cheapest month in which you can book a flight from Watertown, New York to Illinois (average of $144). 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 6h 27m. 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, February is the cheapest month in which you can book a flight from Watertown, New York to Illinois (average of $144). 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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