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O'Hare Intl

$238+ Cheap flights from Watertown, NY (ART) to O'Hare Intl (ORD)

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
ART — ORD
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Watertown to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Watertown (ART) to O'Hare Intl (ORD). 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$238
(American Airlines)
Provider with most accurate pricing for Watertown-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Watertown-Chicago O'Hare Intl flights.
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From Watertown to Chicago O'Hare Intl
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Find flight deals from Watertown to O'Hare Intl

Cheapest flights from Watertown to O'Hare Intl
Explore the most affordable flight options available from Watertown to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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 11/112:33 pmART - ORD
1 stop6h 08mAmerican Airlines
Sat 11/158:30 amORD - ART
1 stop4h 38mAmerican Airlines
Deal found 10/27$238
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/256:00 amART - ORD
1 stop7h 28mAmerican Airlines
Tue 12/24:40 pmORD - ART
1 stop5h 29mAmerican Airlines
Deal found 10/26$385
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/262:33 pmART - ORD
1 stop6h 53mAmerican Airlines
Sat 11/296:47 amORD - ART
1 stop6h 21mAmerican Airlines
Deal found 10/27$425
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/132:30 pmART - ORD
1 stop7h 04mAmerican Airlines
Sat 1/34:51 pmORD - ART
1 stop5h 13mAmerican Airlines
Deal found 10/28$431
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/126:00 amART - ORD
2 stops9h 57mAmerican Airlines
Sun 11/161:15 pmORD - ART
2 stops8h 41mAmerican Airlines
Deal found 10/28$531

Cheapflights Fare Finder

 
Customize your flight search to find flights from Watertown to O'Hare Intl 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 28, 2025.
Use the filters below to find and compare flights from Watertown to Chicago O'Hare Intl Airport that are best for you.

Fly from

Watertown

Fly to

O'Hare Intl

Route

Depart

Return

Price

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 11/12

6:00 am-10:25 am

1 stop5h 25m

Chicago O'Hare Intl

Sun 11/16

6:50 am-2:08 pm

1 stop6h 18m

$238

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 11/11

6:00 am-2:57 pm

2 stops9h 57m

Chicago O'Hare Intl

Sat 11/15

8:30 am-2:08 pm

1 stop4h 38m

$244

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 11/25

6:00 am-12:28 pm

1 stop7h 28m

Chicago O'Hare Intl

Tue 12/2

4:40 pm-11:09 pm

1 stop5h 29m

$385

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 11/26

2:33 pm-8:26 pm

1 stop6h 53m

Chicago O'Hare Intl

Sat 11/29

6:47 am-2:08 pm

1 stop6h 21m

$425

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 12/13

2:30 pm-8:34 pm

1 stop7h 04m

Chicago O'Hare Intl

Sat 1/3

4:51 pm-11:04 pm

1 stop5h 13m

$431

WatertownChicago

ART - ORD

ARTORD

Watertown

Sun 12/14

6:00 am-12:27 pm

1 stop7h 27m

Chicago O'Hare Intl

Sat 1/3

4:51 pm-11:04 pm

1 stop5h 13m

$431

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 4/8

6:24 am-12:16 pm

1 stop6h 52m

Chicago O'Hare Intl

Sat 4/11

6:45 am-12:00 pm

1 stop4h 15m

$534

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

  • Most accurate provider: When it comes to deals on Watertown, New York-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Watertown, New York-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Watertown, New York-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

What is the cheapest month to book a flight from Watertown, New York to Chicago O'Hare Intl Airport?

Currently, December is the cheapest month in which you can book a flight from Watertown, New York to Chicago O'Hare Intl Airport (average of $141). Flying from Watertown, New York to Chicago O'Hare Intl Airport 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 O'Hare Intl. 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 O'Hare Intl?

    For a flight from Watertown to Chicago O'Hare Intl, you will be flying from Watertown. Watertown (ART) is just 5.6 mi from the center of the city. Watertown is the only Watertown airport and it handles 0 outbound flights to Chicago O'Hare Intl per day. 0 airlines have flights to Chicago O'Hare Intl from Watertown on a regular basis.

  • How long is the flight from Watertown, New York to Chicago O'Hare Intl Airport?

    There are many flights that can get you from Watertown, New York to Chicago O'Hare Intl Airport in 5h 25m. Fly via American Airlines to get the fastest option. Airlines will cover a distance of 615 mi.

  • Can I find deals for flights from Watertown to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Watertown to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Watertown to O'Hare Intl?

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

  • Can I find deals for business class flights from Watertown to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Watertown to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, December is the cheapest month in which you can book a flight from Watertown, New York to Chicago O'Hare Intl Airport (average of $141). Flying from Watertown, New York to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Des Plaines
Gurnee
Hoffman Estates
Elgin
Oak Brook
Elk Grove Village
Beloit
Rockford
Naperville
Racine
Downers Grove
Orland Park
Merrillville
Bridgeview
Warrenville
Joliet
Waukegan

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