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Cheap flights from Watertown, New York to Chicago from $351

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Watertown, New York to Chicago departing on 3/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Watertown, New York to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 10:11 am
ART
-
ORD
5h 11m1 stop
American Airlines Logo
2:20 pm - 10:55 pm
ORD
-
ART
7h 35m1 stop
$351American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
6:00 am - 12:35 pm
ART
-
ORD
7h 35m2 stops
American Airlines Logo
2:20 pm - 10:55 pm
ORD
-
ART
7h 35m1 stop
$496American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
6:00 am - 2:38 pm
ART
-
ORD
9h 38m2 stops
American Airlines Logo
2:22 pm - 10:55 pm
ORD
-
ART
7h 33m2 stops
$666American Airlines
Thu, Mar 5 - Sun, Mar 8

American Airlines flights from Watertown, New York to Chicago O'Hare Intl Airport

Our best American Airlines deals on Watertown, New York to Chicago O'Hare Intl Airport flight tickets
American Airlines
Mar 5
ART6:00 amWatertown
5h 11m
1 stop
ORD10:11 amChicago O'Hare Intl
Mar 8
ORD2:20 pmChicago O'Hare Intl
7h 35m
1 stop
ART10:55 pmWatertown
$351
Find similar
American Airlines
Mar 5
ART6:00 amWatertown
7h 35m
2 stops
ORD12:35 pmChicago O'Hare Intl
Mar 8
ORD2:20 pmChicago O'Hare Intl
7h 35m
1 stop
ART10:55 pmWatertown
$496
Find similar
American Airlines
Dec 12
ART2:30 pmWatertown
7h 04m
1 stop
ORD8:34 pmChicago O'Hare Intl
Dec 14
ORD8:29 amChicago O'Hare Intl
4h 36m
1 stop
ART2:05 pmWatertown
$558
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Watertown, New York to Chicago O'Hare Intl Airport 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, momondo users made 832,500 searches. Data last updated December 11, 2025.
Use the filters below to find and compare flights from Watertown, New York to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/5

6:00 am-10:11 am

1 stop5h 11m

Chicago O'Hare Intl

Sun 3/8

2:20 pm-10:55 pm

1 stop7h 35m

$351

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/5

6:00 am-12:35 pm

2 stops7h 35m

Chicago O'Hare Intl

Sun 3/8

2:20 pm-10:55 pm

1 stop7h 35m

$496

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/5

6:00 am-2:38 pm

2 stops9h 38m

Chicago O'Hare Intl

Sun 3/8

2:22 pm-10:55 pm

2 stops7h 33m

$666

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 12/19

6:00 am-10:03 am

1 stop5h 03m

$726

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 12/19

6:00 am-2:12 pm

2 stops9h 12m

$732

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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How to get the cheapest flight ticket from Watertown, New York to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Watertown to Chicago O'Hare Intl?

American Airlines is the most popular carrier operating from Watertown to Chicago O'Hare Intl

When to book flights from Watertown, New York to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Watertown, New York to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Watertown, New York to Chicago O'Hare Intl Airport (ART to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Watertown, New York to Chicago O'Hare Intl Airport

Fastest flight time

5h 11m

Direct flights

None
The fastest flight from Watertown, New York to Chicago O'Hare Intl Airport takes 5h 11m
There are no direct flights from Watertown, New York to Chicago O'Hare Intl Airport. There are no popular flight routes from Watertown, New York to Chicago O'Hare Intl Airport.
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  • How far is Watertown to Chicago O'Hare Intl by plane?

    A flight from Watertown to Chicago O'Hare Intl will travel around 620.7 mi. 5h 11m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Watertown Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Watertown Airport to Chicago O'Hare Intl Airport were last updated today.

  • How old do you have to be to fly from Watertown Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Watertown Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

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Why use momondo?

Why should I use momondo to find a flight deal from Watertown to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Watertown.

Can I find flights from Watertown to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Watertown to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Watertown to Chicago?

momondo helps you find the best flight between Watertown and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Watertown to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Watertown and alert you when they change.

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