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Cheap flights from Watertown, New York to Chicago from $505

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 8/1. 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
1 adult, Economy, 0 bags

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
4:22 pm - 11:30 pm
ART
-
ORD
8h 08m
1 stop
American Airlines Logo
8:30 am - 3:57 pm
ORD
-
ART
6h 27m
1 stop
$505American Airlines
Sat, Aug 1 - Tue, Aug 4
American Airlines Logo
4:22 pm - 11:30 pm
ART
-
ORD
8h 08m
1 stop
American Airlines Logo
3:26 pm - 10:53 pm
ORD
-
ART
6h 27m
1 stop
$532American Airlines
Wed, Jul 29 - Sat, Aug 1
American Airlines Logo
6:00 am - 5:26 pm
ART
-
ORD
12h 26m
2 stops
American Airlines Logo
3:25 pm - 10:55 pm
ORD
-
ART
6h 30m
1 stop
$540American Airlines
Sat, Aug 15 - Mon, Aug 17
American Airlines Logo
6:00 am - 5:26 pm
ART
-
ORD
12h 26m
2 stops
American Airlines Logo
11:45 am - 10:55 pm
ORD
-
ART
10h 10m
2 stops
$554American Airlines
Sat, Aug 15 - Mon, Aug 17
American Airlines Logo
6:00 am - 12:12 pm
ART
-
ORD
7h 12m
1 stop
American Airlines Logo
3:25 pm - 10:55 pm
ORD
-
ART
6h 30m
1 stop
$561American Airlines
Sat, Aug 15 - Mon, Aug 17
American Airlines Logo
4:00 pm - 9:30 pm
ART
-
ORD
6h 30m
1 stop
American Airlines Logo
8:19 am - 3:35 pm
ORD
-
ART
6h 16m
1 stop
$564American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
4:00 pm - 10:30 pm
ART
-
ORD
7h 30m
1 stop
American Airlines Logo
11:45 am - 10:55 pm
ORD
-
ART
10h 10m
2 stops
$579American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
6:00 am - 5:26 pm
ART
-
ORD
12h 26m
2 stops
American Airlines Logo
11:45 am - 10:55 pm
ORD
-
ART
10h 10m
2 stops
$595American Airlines
Sat, Aug 15 - Sun, Aug 16
American Airlines Logo
4:00 pm - 9:30 pm
ART
-
ORD
6h 30m
1 stop
American Airlines Logo
10:10 am - 10:55 pm
ORD
-
ART
11h 45m
2 stops
$620American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
6:00 am - 2:20 pm
ART
-
ORD
9h 20m
2 stops
American Airlines Logo
9:45 am - 3:57 pm
ORD
-
ART
5h 12m
1 stop
$636American Airlines
Sat, Aug 1 - Tue, Aug 4

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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
Aug 1
ART4:22 pmWatertown
8h 08m
1 stop
ORD11:30 pmChicago O'Hare Intl
Aug 4
ORD8:30 amChicago O'Hare Intl
6h 27m
1 stop
ART3:57 pmWatertown
$505
American Airlines
Jul 29
ART4:22 pmWatertown
8h 08m
1 stop
ORD11:30 pmChicago O'Hare Intl
Aug 1
ORD3:26 pmChicago O'Hare Intl
6h 27m
1 stop
ART10:53 pmWatertown
$532
American Airlines
Aug 15
ART6:00 amWatertown
12h 26m
2 stops
ORD5:26 pmChicago O'Hare Intl
Aug 17
ORD3:25 pmChicago O'Hare Intl
6h 30m
1 stop
ART10:55 pmWatertown
$540

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 July 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

Cheapest round-trip

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 8/1

4:22 pm-11:30 pm

1 stop8h 08m

Chicago O'Hare Intl

Tue 8/4

8:30 am-3:57 pm

1 stop6h 27m

$505

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 7/29

4:22 pm-11:30 pm

1 stop8h 08m

Chicago O'Hare Intl

Sat 8/1

3:26 pm-10:53 pm

1 stop6h 27m

$532

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 8/15

6:00 am-5:26 pm

2 stops12h 26m

Chicago O'Hare Intl

Mon 8/17

3:25 pm-10:55 pm

1 stop6h 30m

$540

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 8/15

6:00 am-5:26 pm

2 stops12h 26m

Chicago O'Hare Intl

Mon 8/17

11:45 am-10:55 pm

2 stops10h 10m

$554

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 8/15

6:00 am-12:12 pm

1 stop7h 12m

Chicago O'Hare Intl

Mon 8/17

3:25 pm-10:55 pm

1 stop6h 30m

$561
Quickest round-trip

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 8/13

4:00 pm-9:30 pm

1 stop6h 30m

Chicago O'Hare Intl

Sun 8/16

8:19 am-3:35 pm

1 stop6h 16m

$564

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 8/13

4:00 pm-10:30 pm

1 stop7h 30m

Chicago O'Hare Intl

Mon 8/17

11:45 am-10:55 pm

2 stops10h 10m

$579

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 8/15

6:00 am-5:26 pm

2 stops12h 26m

Chicago O'Hare Intl

Sun 8/16

11:45 am-10:55 pm

2 stops10h 10m

$595

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 8/13

4:00 pm-9:30 pm

1 stop6h 30m

Chicago O'Hare Intl

Sun 8/16

10:10 am-10:55 pm

2 stops11h 45m

$620

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 8/1

6:00 am-2:20 pm

2 stops9h 20m

Chicago O'Hare Intl

Tue 8/4

9:45 am-3:57 pm

1 stop5h 12m

$636

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 airlines fly to Chicago O'Hare Intl Airport?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Watertown, New York according to our data. American Airlines is the first choice among our users, with 60% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

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

8h 08m

Direct flights

None
The fastest flight from Watertown, New York to Chicago O'Hare Intl Airport takes 8h 08m
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.
Search flight deals

Frequently asked questions about flying from Watertown, New York to Chicago O'Hare Intl Airport

  • 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. 8h 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
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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