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Cheap flights from Watertown, New York to Chicago from $318

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 4/15. 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 - 10:41 am
ART
-
ORD
5h 41m
1 stop
American Airlines Logo
5:00 am - 10:59 am
ORD
-
ART
4h 59m
1 stop
$318American Airlines
Wed, Apr 15 - Sun, Apr 19
American Airlines Logo
6:00 am - 12:36 pm
ART
-
ORD
7h 36m
2 stops
American Airlines Logo
5:00 am - 10:59 am
ORD
-
ART
4h 59m
1 stop
$324American Airlines
Wed, Apr 15 - Sun, Apr 19
American Airlines Logo
11:25 am - 7:52 pm
ART
-
ORD
9h 27m
2 stops
American Airlines Logo
5:00 am - 10:59 am
ORD
-
ART
4h 59m
1 stop
$404American Airlines
Tue, Apr 14 - Sat, Apr 18
American Airlines Logo
11:25 am - 7:22 pm
ART
-
ORD
8h 57m
2 stops
American Airlines Logo
11:15 am - 11:28 pm
ORD
-
ART
11h 13m
2 stops
$409American Airlines
Tue, Apr 14 - Sat, Apr 18
American Airlines Logo
6:00 am - 12:38 pm
ART
-
ORD
7h 38m
1 stop
American Airlines Logo
5:45 pm - 11:28 pm
ORD
-
ART
4h 43m
1 stop
$505American Airlines
Tue, Apr 14 - Sat, Apr 18
American Airlines Logo
6:00 am - 11:27 am
ART
-
ORD
6h 27m
1 stop
American Airlines Logo
3:21 pm - 10:52 pm
ORD
-
ART
6h 31m
1 stop
$506American Airlines
Sat, May 30 - Sat, Jun 27
American Airlines Logo
6:00 am - 12:18 pm
ART
-
ORD
7h 18m
2 stops
American Airlines Logo
5:16 pm - 10:52 pm
ORD
-
ART
4h 36m
1 stop
$512American Airlines
Sat, May 30 - Sat, Jun 27
American Airlines Logo
6:00 am - 12:18 pm
ART
-
ORD
7h 18m
2 stops
American Airlines Logo
1:19 pm - 10:52 pm
ORD
-
ART
8h 33m
2 stops
$541American Airlines
Sat, May 30 - Sat, Jun 27
American Airlines Logo
4:22 pm - 9:45 pm
ART
-
ORD
6h 23m
1 stop
American Airlines Logo
4:00 pm - 11:52 pm
ORD
-
ART
6h 52m
1 stop
$555American Airlines
Sat, Jul 25 - Sat, Aug 15
American Airlines Logo
4:22 pm - 9:45 pm
ART
-
ORD
6h 23m
1 stop
American Airlines Logo
5:15 pm - 11:52 pm
ORD
-
ART
5h 37m
1 stop
$558American Airlines
Sat, Jul 25 - Mon, Aug 17

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
Apr 11
ART11:25 amWatertown
7h 04m
1 stop
ORD5:29 pmChicago O'Hare Intl
Apr 15
ORD5:00 amChicago O'Hare Intl
4h 59m
1 stop
ART10:59 amWatertown
$318
American Airlines
Apr 11
ART11:25 amWatertown
7h 33m
2 stops
ORD5:58 pmChicago O'Hare Intl
Apr 15
ORD5:00 amChicago O'Hare Intl
4h 59m
1 stop
ART10:59 amWatertown
$324
American Airlines
Apr 10
ART6:00 amWatertown
5h 41m
1 stop
ORD10:41 amChicago O'Hare Intl
Apr 26
ORD5:00 amChicago O'Hare Intl
4h 59m
1 stop
ART10:59 amWatertown
$338

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 April 1, 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
Quickest round-trip

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 4/15

6:00 am-10:41 am

1 stop5h 41m

Chicago O'Hare Intl

Sun 4/19

5:00 am-10:59 am

1 stop4h 59m

$318

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 4/15

6:00 am-12:36 pm

2 stops7h 36m

Chicago O'Hare Intl

Sun 4/19

5:00 am-10:59 am

1 stop4h 59m

$324

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 4/14

11:25 am-7:52 pm

2 stops9h 27m

Chicago O'Hare Intl

Sat 4/18

5:00 am-10:59 am

1 stop4h 59m

$404

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 4/14

11:25 am-7:22 pm

2 stops8h 57m

Chicago O'Hare Intl

Sat 4/18

11:15 am-11:28 pm

2 stops11h 13m

$409

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 4/14

6:00 am-12:38 pm

1 stop7h 38m

Chicago O'Hare Intl

Sat 4/18

5:45 pm-11:28 pm

1 stop4h 43m

$505

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 5/30

6:00 am-11:27 am

1 stop6h 27m

Chicago O'Hare Intl

Sat 6/27

3:21 pm-10:52 pm

1 stop6h 31m

$506

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 5/30

6:00 am-12:18 pm

2 stops7h 18m

Chicago O'Hare Intl

Sat 6/27

5:16 pm-10:52 pm

1 stop4h 36m

$512

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 5/30

6:00 am-12:18 pm

2 stops7h 18m

Chicago O'Hare Intl

Sat 6/27

1:19 pm-10:52 pm

2 stops8h 33m

$541

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 7/25

4:22 pm-9:45 pm

1 stop6h 23m

Chicago O'Hare Intl

Sat 8/15

4:00 pm-11:52 pm

1 stop6h 52m

$555

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 7/25

4:22 pm-9:45 pm

1 stop6h 23m

Chicago O'Hare Intl

Mon 8/17

5:15 pm-11:52 pm

1 stop5h 37m

$558

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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

Fastest flight time

5h 41m

Direct flights

None
The fastest flight from Watertown, New York to Chicago O'Hare Intl Airport takes 5h 41m
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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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. 5h 41m 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
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Aurora
Racine
Hammond
Elgin
Tinley Park
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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