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$298+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
ART — CHI
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
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 March 10, 2026.

This American Airlines deal was found by Cheapflights users on 3/9. 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.
Tue 3/244:01 pm
ART
-
ORD
1 stop6h 17m
American Airlines
Sat 3/284:48 pm
ORD
-
ART
1 stop5h 07m
American Airlines
Deal found 3/9$298
This American Airlines deal was found by Cheapflights users on 3/10. 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.
Fri 7/314:09 pm
ART
-
ORD
1 stop6h 36m
American Airlines
Tue 8/49:45 am
ORD
-
ART
1 stop4h 59m
American Airlines
Deal found 3/10$411
This American Airlines deal was found by Cheapflights users on 3/9. 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.
Thu 3/266:00 am
ART
-
ORD
2 stops7h 35m
American Airlines
Sun 3/298:23 am
ORD
-
ART
1 stop5h 56m
American Airlines
Deal found 3/9$423
This American Airlines deal was found by Cheapflights users on 3/7. 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 3/116:00 am
ART
-
ORD
1 stop7h 16m
American Airlines
Sat 3/148:23 am
ORD
-
ART
1 stop5h 56m
American Airlines
Deal found 3/7$582
This American Airlines deal was found by Cheapflights users on 3/7. 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 3/126:00 am
ART
-
ORD
1 stop7h 16m
American Airlines
Sat 3/148:23 am
ORD
-
ART
1 stop5h 56m
American Airlines
Deal found 3/7$590
This American Airlines deal was found by Cheapflights users on 3/7. 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 3/116:00 am
ART
-
ORD
1 stop5h 12m
American Airlines
Mon 3/167:12 am
ORD
-
ART
2 stops7h 07m
American Airlines
Deal found 3/7$596

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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$298
(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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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 March 10, 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
Quickest round-trip

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 3/24

4:01 pm-9:18 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 3/28

4:48 pm-10:55 pm

1 stop5h 07m

$298

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/26

6:00 am-12:35 pm

2 stops7h 35m

Chicago O'Hare Intl

Sun 3/29

8:23 am-3:19 pm

1 stop5h 56m

$423

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 7/31

4:09 pm-11:59 pm

2 stops8h 50m

Chicago O'Hare Intl

Tue 8/4

9:45 am-3:44 pm

1 stop4h 59m

$531

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 6/12

6:00 am-10:34 am

1 stop5h 34m

Chicago O'Hare Intl

Fri 6/26

3:21 pm-10:52 pm

1 stop6h 31m

$822

WatertownChicago

ART - ORD

ARTORD

Watertown

Sun 3/22

6:00 am-12:16 pm

1 stop7h 16m

Chicago O'Hare Intl

Thu 3/26

8:23 am-3:19 pm

1 stop5h 56m

$1,000

WatertownChicago

ART - ORD

ARTORD

Watertown

Mon 4/20

6:00 am-12:18 pm

1 stop7h 18m

Chicago O'Hare Intl

Thu 4/23

5:45 pm-11:23 pm

1 stop4h 38m

$1,000

WatertownChicago

ART - ORD

ARTORD

Watertown

Mon 3/23

6:00 am-12:16 pm

1 stop7h 16m

Chicago O'Hare Intl

Fri 3/27

8:23 am-3:19 pm

1 stop5h 56m

$1,000
Cheapest one-way
Quickest one-way

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 5/15

11:25 am-5:29 pm

1 stop7h 04m

$500

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

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 March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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

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

Currently, June is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $209). Flying from Watertown, New York to Chicago in March 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 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 6h 17m. 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, June is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $209). Flying from Watertown, New York to Chicago in March 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?

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

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