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Cheap flights from Watertown, New York to Chicago from $238

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 11/11. 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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Cheap round-trip flights

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American Airlines Logo
2:33 pm - 7:41 pmART-ORD
6h 08m1 stop
American Airlines Logo
8:30 am - 2:08 pmORD-ART
4h 38m1 stop
$238American Airlines
Find Deal
Tue, Nov 11 - Sat, Nov 15
American Airlines Logo
6:00 am - 2:57 pmART-ORD
9h 57m2 stops
American Airlines Logo
8:30 am - 2:08 pmORD-ART
4h 38m1 stop
$244American Airlines
Find Deal
Tue, Nov 11 - Sat, Nov 15
American Airlines Logo
6:00 am - 2:57 pmART-ORD
9h 57m2 stops
American Airlines Logo
1:15 pm - 10:56 pmORD-ART
8h 41m2 stops
$356American Airlines
Find Deal
Tue, Nov 11 - Sat, Nov 15
American Airlines Logo
6:00 am - 12:28 pmART-ORD
7h 28m1 stop
American Airlines Logo
4:40 pm - 11:09 pmORD-ART
5h 29m1 stop
$385American Airlines
Find Deal
Tue, Nov 25 - Tue, Dec 2
American Airlines Logo
6:00 am - 12:28 pmART-ORD
7h 28m1 stop
American Airlines Logo
3:03 pm - 11:09 pmORD-ART
7h 06m2 stops
$391American Airlines
Find Deal
Tue, Nov 25 - Tue, Dec 2
American Airlines Logo
6:00 am - 12:28 pmART-ORD
7h 28m1 stop
American Airlines Logo
6:47 am - 2:08 pmORD-ART
6h 21m1 stop
$397American Airlines
Find Deal
Tue, Nov 25 - Mon, Dec 1
American Airlines Logo
2:33 pm - 8:26 pmART-ORD
6h 53m1 stop
American Airlines Logo
6:47 am - 2:08 pmORD-ART
6h 21m1 stop
$425American Airlines
Find Deal
Wed, Nov 26 - Sat, Nov 29
American Airlines Logo
6:00 am - 12:56 pmART-ORD
7h 56m2 stops
American Airlines Logo
3:03 pm - 11:09 pmORD-ART
7h 06m2 stops
$463American Airlines
Find Deal
Tue, Nov 25 - Tue, Dec 2
American Airlines Logo
6:00 am - 2:14 pmART-ORD
9h 14m2 stops
American Airlines Logo
6:47 am - 2:08 pmORD-ART
6h 21m1 stop
$470American Airlines
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Tue, Nov 25 - Mon, Dec 1
American Airlines Logo
6:24 am - 12:16 pmART-ORD
6h 52m1 stop
American Airlines Logo
6:45 am - 12:00 pmORD-ART
4h 15m1 stop
$534American Airlines
Find Deal
Wed, Apr 8 - Sat, Apr 11

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
Nov 11
ART2:33 pmWatertown
6h 08m
1 stop
ORD7:41 pmChicago O'Hare Intl
Nov 15
ORD8:30 amChicago O'Hare Intl
4h 38m
1 stop
ART2:08 pmWatertown
$238
Find similar
American Airlines
Nov 11
ART6:00 amWatertown
9h 57m
2 stops
ORD2:57 pmChicago O'Hare Intl
Nov 15
ORD8:30 amChicago O'Hare Intl
4h 38m
1 stop
ART2:08 pmWatertown
$244
Find similar
American Airlines
Nov 11
ART6:00 amWatertown
9h 57m
2 stops
ORD2:57 pmChicago O'Hare Intl
Nov 15
ORD1:15 pmChicago O'Hare Intl
8h 41m
2 stops
ART10:56 pmWatertown
$356
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 October 27, 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

Tue 11/11

2:33 pm-7:41 pm

1 stop6h 08m

Chicago O'Hare Intl

Sat 11/15

8:30 am-2:08 pm

1 stop4h 38m

$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 11/11

6:00 am-2:57 pm

2 stops9h 57m

Chicago O'Hare Intl

Sat 11/15

1:15 pm-10:56 pm

2 stops8h 41m

$356

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

Tue 11/25

6:00 am-12:28 pm

1 stop7h 28m

Chicago O'Hare Intl

Tue 12/2

3:03 pm-11:09 pm

2 stops7h 06m

$391

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 11/25

6:00 am-12:28 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 12/1

6:47 am-2:08 pm

1 stop6h 21m

$397

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

Tue 11/25

6:00 am-12:56 pm

2 stops7h 56m

Chicago O'Hare Intl

Tue 12/2

3:03 pm-11:09 pm

2 stops7h 06m

$463

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 11/25

6:00 am-2:14 pm

2 stops9h 14m

Chicago O'Hare Intl

Mon 12/1

6:47 am-2:08 pm

1 stop6h 21m

$470

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.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Chicago from

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

Direct flights

None
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. 6h 08m 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?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Elgin
Aurora
Benton Harbor

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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