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$318+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
ART — CHI
May 10 — May 171
Sun 5/10
Sun 5/17
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 April 10, 2026.

This American Airlines deal was found by Cheapflights users on 4/6. 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 4/216:00 am
ART
-
ORD
1 stop7h 38m
American Airlines
Sat 4/255:00 am
ORD
-
ART
1 stop4h 59m
American Airlines
Deal found 4/6$318
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Fri 4/176:00 am
ART
-
ORD
2 stops7h 36m
American Airlines
Mon 4/205:45 pm
ORD
-
ART
1 stop4h 38m
American Airlines
Deal found 4/7$424
This American Airlines deal was found by Cheapflights users on 4/8. 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 4/236:00 am
ART
-
ORD
1 stop5h 41m
American Airlines
Mon 4/275:45 pm
ORD
-
ART
1 stop4h 38m
American Airlines
Deal found 4/8$503
This American Airlines deal was found by Cheapflights users on 4/9. 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.
Wed 5/274:06 pm
ART
-
ORD
2 stops8h 53m
American Airlines
Sun 5/318:32 am
ORD
-
ART
1 stop6h 07m
American Airlines
Deal found 4/9$509
This American Airlines deal was found by Cheapflights users on 4/5. 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 4/2011:25 am
ART
-
ORD
1 stop11h 10m
American Airlines
Fri 4/247:15 pm
ORD
-
ART
1 stop14h 44m
American Airlines
Deal found 4/5$875
This American Airlines deal was found by Cheapflights users on 4/6. 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 4/86:00 am
ART
-
ORD
2 stops8h 33m
American Airlines
Wed 4/83:31 pm
ORD
-
ART
1 stop6h 52m
American Airlines
Deal found 4/6$920

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 April 10, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$318
(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 April 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

Fri 4/24

11:25 am-5:29 pm

1 stop7h 04m

Chicago O'Hare Intl

Tue 4/28

5:00 am-10:59 am

1 stop4h 59m

$318

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 4/21

6:00 am-12:38 pm

1 stop7h 38m

Chicago O'Hare Intl

Sat 4/25

5:00 am-10:59 am

1 stop4h 59m

$318

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 4/23

11:25 am-5:58 pm

2 stops7h 33m

Chicago O'Hare Intl

Mon 4/27

5:45 pm-11:23 pm

1 stop4h 38m

$324

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 5/27

4:06 pm-9:39 pm

1 stop6h 33m

Chicago O'Hare Intl

Sun 5/31

8:32 am-3:39 pm

1 stop6h 07m

$503

WatertownChicago

ART - ORD

ARTORD

Watertown

Mon 4/20

11:25 am-9:35 pm

1 stop11h 10m

Chicago O'Hare Intl

Fri 4/24

7:15 pm-10:59 am

1 stop14h 44m

$875
Cheapest one-way
Quickest one-way

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 7/29

4:09 pm-9:45 pm

1 stop6h 36m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/7

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Watertown, New York-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Watertown, New York-Chicago flight deals on Cheapflights vs. Expedia <90% 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 Expedia the most. Expedia 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, September is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $207). Flying from Watertown, New York to Chicago in March is currently the most expensive (average of $275). 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 7h 04m. 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, September is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $207). Flying from Watertown, New York to Chicago in March is currently the most expensive (average of $275). 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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