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Cheap flights from Chicago to Watertown from $399

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Watertown departing on 10/12. 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 Chicago to Watertown

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:00 am - 10:27 pmORD  Chicago O'Hare Intl-ART Watertown
14h 27m2 stops Cleveland Hopkins Intl Philadelphia
American Airlines Logo
6:00 am - 10:00 pmART  Watertown-ORD Chicago O'Hare Intl
17h 00m2 stops Philadelphia Cleveland Hopkins Intl
$542American Airlines
Fri, Oct 30 - Tue, Nov 10
American Airlines Logo
7:00 am - 10:27 pmORD  Chicago O'Hare Intl-ART Watertown
14h 27m2 stops Cleveland Hopkins Intl Philadelphia
American Airlines Logo
5:46 pm - 11:30 pmART  Watertown-ORD Chicago O'Hare Intl
6h 44m1 stop Philadelphia
$547American Airlines
Fri, Oct 30 - Wed, Nov 4
American Airlines Logo
7:00 am - 10:27 pmORD  Chicago O'Hare Intl-ART Watertown
14h 27m2 stops Cleveland Hopkins Intl Philadelphia
American Airlines Logo
6:00 am - 12:19 pmART  Watertown-ORD Chicago O'Hare Intl
7h 19m1 stop Philadelphia
$550American Airlines
Fri, Oct 30 - Thu, Nov 5
American Airlines Logo
1:22 pm - 6:57 pmORD  Chicago O'Hare Intl-ART Watertown
4h 35m1 stop Philadelphia
American Airlines Logo
5:46 pm - 6:00 pmART  Watertown-ORD Chicago O'Hare Intl
25h 14m2 stops Philadelphia Cleveland Hopkins Intl
$564American Airlines
Wed, Oct 28 - Sun, Nov 8
American Airlines Logo
8:29 am - 5:00 pmORD  Chicago O'Hare Intl-ART Watertown
7h 31m1 stop Philadelphia
American Airlines Logo
6:00 am - 10:00 pmART  Watertown-ORD Chicago O'Hare Intl
17h 00m2 stops Philadelphia Cleveland Hopkins Intl
$567American Airlines
Thu, Oct 29 - Tue, Nov 10
American Airlines Logo
1:22 pm - 6:57 pmORD  Chicago O'Hare Intl-ART Watertown
4h 35m1 stop Philadelphia
American Airlines Logo
5:46 pm - 11:30 pmART  Watertown-ORD Chicago O'Hare Intl
6h 44m1 stop Philadelphia
$568American Airlines
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
1:22 pm - 6:57 pmORD  Chicago O'Hare Intl-ART Watertown
4h 35m1 stop Philadelphia
American Airlines Logo
6:00 am - 11:04 amART  Watertown-ORD Chicago O'Hare Intl
6h 04m1 stop Philadelphia
$571American Airlines
Wed, Oct 28 - Fri, Nov 6
American Airlines Logo
3:37 pm - 10:27 pmORD  Chicago O'Hare Intl-ART Watertown
5h 50m1 stop Philadelphia
American Airlines Logo
5:46 pm - 11:30 pmART  Watertown-ORD Chicago O'Hare Intl
6h 44m1 stop Philadelphia
$574American Airlines
Thu, Oct 29 - Thu, Nov 5
American Airlines Logo
9:05 pm - 5:21 pmORD  Chicago O'Hare Intl-ART Watertown
19h 16m2 stops Pittsburgh Philadelphia
American Airlines Logo
6:00 am - 10:00 pmART  Watertown-ORD Chicago O'Hare Intl
17h 00m2 stops Philadelphia Cleveland Hopkins Intl
$584American Airlines
Tue, Nov 3 - Tue, Nov 10
American Airlines Logo
10:51 pm - 5:00 pmORD  Chicago O'Hare Intl-ART Watertown
17h 09m2 stops Nashville Intl Philadelphia
American Airlines Logo
6:00 am - 11:04 amART  Watertown-ORD Chicago O'Hare Intl
6h 04m1 stop Philadelphia
$586American Airlines
Wed, Oct 28 - Sat, Nov 7

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American Airlines flights from Chicago to Watertown, New York

Our best American Airlines deals on Chicago to Watertown, New York flight tickets
American Airlines
Oct 30
ORD7:00 amChicago O'Hare Intl
14h 27m
2 stops
ART10:27 pmWatertown
Nov 10
ART6:00 amWatertown
17h 00m
2 stops
ORD10:00 pmChicago O'Hare Intl
$542
American Airlines
Oct 30
ORD7:00 amChicago O'Hare Intl
14h 27m
2 stops
ART10:27 pmWatertown
Nov 4
ART5:46 pmWatertown
6h 44m
1 stop
ORD11:30 pmChicago O'Hare Intl
$547
American Airlines
Oct 30
ORD7:00 amChicago O'Hare Intl
14h 27m
2 stops
ART10:27 pmWatertown
Nov 5
ART6:00 amWatertown
7h 19m
1 stop
ORD12:19 pmChicago O'Hare Intl
$550

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Watertown, New York 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 August 9, 2026.
Use the filters below to find and compare flights from Chicago to Watertown, New York that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Fri 10/30

7:00 am-10:27 pm

2 stops14h 27m

Watertown

Tue 11/10

6:00 am-10:00 pm

2 stops17h 00m

$542

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Fri 10/30

7:00 am-10:27 pm

2 stops14h 27m

Watertown

Wed 11/4

5:46 pm-11:30 pm

1 stop6h 44m

$547

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Fri 10/30

7:00 am-10:27 pm

2 stops14h 27m

Watertown

Thu 11/5

6:00 am-12:19 pm

1 stop7h 19m

$550

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Wed 10/28

1:22 pm-6:57 pm

1 stop4h 35m

Watertown

Sun 11/8

5:46 pm-6:00 pm

2 stops25h 14m

$564

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Thu 10/29

8:29 am-5:00 pm

1 stop7h 31m

Watertown

Tue 11/10

6:00 am-10:00 pm

2 stops17h 00m

$567

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Wed 10/28

1:22 pm-6:57 pm

1 stop4h 35m

Watertown

Wed 11/4

5:46 pm-11:30 pm

1 stop6h 44m

$568
Quickest round-trip

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Wed 10/28

1:22 pm-6:57 pm

1 stop4h 35m

Watertown

Fri 11/6

6:00 am-11:04 am

1 stop6h 04m

$571

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Thu 10/29

3:37 pm-10:27 pm

1 stop5h 50m

Watertown

Thu 11/5

5:46 pm-11:30 pm

1 stop6h 44m

$574

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Tue 11/3

9:05 pm-5:21 pm

2 stops19h 16m

Watertown

Tue 11/10

6:00 am-10:00 pm

2 stops17h 00m

$584

ChicagoWatertown

ORD Chicago O'Hare Intl - ART Watertown

ORDART

Chicago O'Hare Intl

Wed 10/28

10:51 pm-5:00 pm

2 stops17h 09m

Watertown

Sat 11/7

6:00 am-11:04 am

1 stop6h 04m

$586

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to Watertown from

How to get the cheapest flight ticket from Chicago to Watertown, New York

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 Chicago to Watertown?

American Airlines is the most popular carrier operating from Chicago to Watertown

When to book flights from Chicago to Watertown, New York

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

Cheap Chicago to Watertown, New York (CHI to ART) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Watertown, New York

Fastest flight time

6h 20m

Direct flights

None
The fastest flight from Chicago to Watertown, New York takes 6h 20m
There are no direct flights from Chicago to Watertown, New York. There are no popular flight routes from Chicago to Watertown, New York.
Search flight deals

Frequently asked questions about flying from Chicago to Watertown, New York

  • How far is Chicago to Watertown by plane?

    A flight from Chicago to Watertown will travel around 609.3 mi. Flights usually cover this in 6h 20m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Watertown Airport?

    Prices for flights from Chicago to Watertown Airport were last updated today.

  • How old do you have to be to fly from Chicago to Watertown Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Watertown Airport.

  • What documentation or ID do you need to fly to Watertown Airport?

    The travel and health documents required for your trip to Watertown Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Watertown Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Watertown?

Book flights to Watertown if you plan to visit one of these locations
Alexandria Bay
Clayton

Why use momondo?

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

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 Watertown from Chicago.

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

All flight searches from Chicago to Watertown on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Chicago to Watertown flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Chicago to Watertown flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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