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Cheap flights from Watertown, New York to Chicago from $403

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 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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 - 12:05 pm
ART
-
ORD
7h 05m
1 stop
American Airlines Logo
7:10 am - 3:41 pm
ORD
-
ART
7h 31m
2 stops
$403American Airlines
Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
6:00 am - 2:16 pm
ART
-
ORD
9h 16m
2 stops
American Airlines Logo
7:10 am - 3:41 pm
ORD
-
ART
7h 31m
2 stops
$408American Airlines
Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
6:00 am - 10:12 am
ART
-
ORD
5h 12m
1 stop
American Airlines Logo
4:48 pm - 10:55 pm
ORD
-
ART
5h 07m
1 stop
$505American Airlines
Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
6:00 am - 12:02 pm
ART
-
ORD
7h 02m
1 stop
American Airlines Logo
1:32 pm - 10:55 pm
ORD
-
ART
8h 23m
2 stops
$688American Airlines
Sat, Feb 28 - Sat, Feb 28
American Airlines Logo
6:00 am - 12:02 pm
ART
-
ORD
7h 02m
1 stop
American Airlines Logo
4:48 pm - 10:55 pm
ORD
-
ART
5h 07m
1 stop
$886American Airlines
Sat, Feb 28 - Sat, Feb 28
American Airlines Logo
6:00 am - 12:35 pm
ART
-
ORD
7h 35m
2 stops
American Airlines Logo
1:39 pm - 10:55 pm
ORD
-
ART
8h 16m
2 stops
$953American Airlines
Sat, Feb 28 - Sat, Feb 28
American Airlines Logo
6:00 am - 10:12 am
ART
-
ORD
5h 12m
1 stop
American Airlines Logo
4:48 pm - 10:55 pm
ORD
-
ART
5h 07m
1 stop
$980American Airlines
Sun, Feb 22 - Thu, Feb 26
American Airlines Logo
6:00 am - 2:16 pm
ART
-
ORD
9h 16m
2 stops
American Airlines Logo
2:40 pm - 10:55 pm
ORD
-
ART
7h 15m
1 stop
$986American Airlines
Sun, Feb 22 - Thu, Feb 26
American Airlines Logo
6:00 am - 2:16 pm
ART
-
ORD
9h 16m
2 stops
American Airlines Logo
7:10 am - 3:41 pm
ORD
-
ART
7h 31m
2 stops
$991American Airlines
Sun, Feb 22 - Thu, Feb 26

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
Feb 19
ART6:00 amWatertown
7h 05m
1 stop
ORD12:05 pmChicago O'Hare Intl
Feb 23
ORD7:10 amChicago O'Hare Intl
7h 31m
2 stops
ART3:41 pmWatertown
$403
American Airlines
Feb 19
ART6:00 amWatertown
9h 16m
2 stops
ORD2:16 pmChicago O'Hare Intl
Feb 23
ORD7:10 amChicago O'Hare Intl
7h 31m
2 stops
ART3:41 pmWatertown
$408
American Airlines
Feb 11
ART7:00 amWatertown
5h 08m
1 stop
ORD11:08 amChicago O'Hare Intl
Mar 16
ORD4:48 pmChicago O'Hare Intl
5h 07m
1 stop
ART10:55 pmWatertown
$504

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 February 7, 2026.
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 2/19

6:00 am-12:05 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 2/23

7:10 am-3:41 pm

2 stops7h 31m

$403

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 2/19

6:00 am-2:16 pm

2 stops9h 16m

Chicago O'Hare Intl

Mon 2/23

7:10 am-3:41 pm

2 stops7h 31m

$408

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 2/19

6:00 am-10:12 am

1 stop5h 12m

Chicago O'Hare Intl

Mon 2/23

4:48 pm-10:55 pm

1 stop5h 07m

$505

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 2/28

6:00 am-12:02 pm

1 stop7h 02m

Chicago O'Hare Intl

Sat 2/28

1:32 pm-10:55 pm

2 stops8h 23m

$688

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 2/28

6:00 am-12:02 pm

1 stop7h 02m

Chicago O'Hare Intl

Sat 2/28

4:48 pm-10:55 pm

1 stop5h 07m

$886

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 2/28

6:00 am-12:35 pm

2 stops7h 35m

Chicago O'Hare Intl

Sat 2/28

1:39 pm-10:55 pm

2 stops8h 16m

$953

WatertownChicago

ART - ORD

ARTORD

Watertown

Sun 2/22

6:00 am-10:12 am

1 stop5h 12m

Chicago O'Hare Intl

Thu 2/26

4:48 pm-10:55 pm

1 stop5h 07m

$980

WatertownChicago

ART - ORD

ARTORD

Watertown

Sun 2/22

6:00 am-2:16 pm

2 stops9h 16m

Chicago O'Hare Intl

Thu 2/26

2:40 pm-10:55 pm

1 stop7h 15m

$986

WatertownChicago

ART - ORD

ARTORD

Watertown

Sun 2/22

6:00 am-2:16 pm

2 stops9h 16m

Chicago O'Hare Intl

Thu 2/26

7:10 am-3:41 pm

2 stops7h 31m

$991

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 12m

Direct flights

None
The fastest flight from Watertown, New York to Chicago O'Hare Intl Airport takes 5h 12m
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 12m 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.

  • How do I get Price Alerts for flights from Watertown, New York to Chicago O'Hare Intl Airport?

    Price Alerts will notify you by email when the price for flights to Chicago O'Hare Intl Airport from Watertown, New York decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

  • How can I save money on flights from Watertown, New York to Chicago O'Hare Intl Airport with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We compare prices from 700+ competitors to help you find the price that works best for you. momondo operates in over 30 international markets, bringing you access to a wide range of fares and deals. Search for your travel using momondo for a diverse range of options from airlines and OTAs.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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South Holland

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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