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Cheap flights from Watertown, New York to Chicago from $298

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 3/24. 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

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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
4:01 pm - 9:18 pm
ART
-
ORD
6h 17m
1 stop
American Airlines Logo
4:48 pm - 10:55 pm
ORD
-
ART
5h 07m
1 stop
$298American Airlines
Tue, Mar 24 - Sat, Mar 28
American Airlines Logo
4:01 pm - 12:06 am
ART
-
ORD
9h 05m
2 stops
American Airlines Logo
4:48 pm - 10:55 pm
ORD
-
ART
5h 07m
1 stop
$304American Airlines
Tue, Mar 24 - Sat, Mar 28
American Airlines Logo
4:09 pm - 9:45 pm
ART
-
ORD
6h 36m
1 stop
American Airlines Logo
9:45 am - 3:44 pm
ORD
-
ART
4h 59m
1 stop
$411American Airlines
Fri, Jul 31 - Tue, Aug 4
American Airlines Logo
4:01 pm - 12:06 am
ART
-
ORD
9h 05m
2 stops
American Airlines Logo
1:39 pm - 10:55 pm
ORD
-
ART
8h 16m
2 stops
$416American Airlines
Tue, Mar 24 - Sat, Mar 28
American Airlines Logo
6:00 am - 12:35 pm
ART
-
ORD
7h 35m
2 stops
American Airlines Logo
8:23 am - 3:19 pm
ORD
-
ART
5h 56m
1 stop
$423American Airlines
Thu, Mar 26 - Sun, Mar 29
American Airlines Logo
6:00 am - 10:12 am
ART
-
ORD
5h 12m
1 stop
American Airlines Logo
8:23 am - 3:19 pm
ORD
-
ART
5h 56m
1 stop
$437American Airlines
Thu, Mar 26 - Mon, Mar 30
American Airlines Logo
6:00 am - 12:16 pm
ART
-
ORD
7h 16m
1 stop
American Airlines Logo
1:39 pm - 10:55 pm
ORD
-
ART
8h 16m
2 stops
$443American Airlines
Thu, Mar 26 - Mon, Mar 30
American Airlines Logo
4:06 pm - 9:36 pm
ART
-
ORD
6h 30m
1 stop
American Airlines Logo
5:16 pm - 10:52 pm
ORD
-
ART
4h 36m
1 stop
$517American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
4:06 pm - 11:59 pm
ART
-
ORD
8h 53m
2 stops
American Airlines Logo
5:16 pm - 10:52 pm
ORD
-
ART
4h 36m
1 stop
$522American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
4:09 pm - 11:59 pm
ART
-
ORD
8h 50m
2 stops
American Airlines Logo
9:45 am - 3:44 pm
ORD
-
ART
4h 59m
1 stop
$531American Airlines
Fri, Jul 31 - Tue, Aug 4

American Airlines flights from Watertown, New York to Chicago

Our best American Airlines deals on Watertown, New York to Chicago flight tickets
American Airlines
Mar 24
ART4:01 pmWatertown
6h 17m
1 stop
ORD9:18 pmChicago O'Hare Intl
Mar 28
ORD4:48 pmChicago O'Hare Intl
5h 07m
1 stop
ART10:55 pmWatertown
$298
American Airlines
Mar 24
ART4:01 pmWatertown
9h 05m
2 stops
ORD12:06 amChicago O'Hare Intl
Mar 28
ORD4:48 pmChicago O'Hare Intl
5h 07m
1 stop
ART10:55 pmWatertown
$304
American Airlines
Jul 31
ART4:09 pmWatertown
6h 36m
1 stop
ORD9:45 pmChicago O'Hare Intl
Aug 4
ORD9:45 amChicago O'Hare Intl
4h 59m
1 stop
ART3:44 pmWatertown
$411

momondo Fare Finder

 
Customize your flight search to find flights from Watertown, New York to Chicago 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 March 14, 2026.
Use the filters below to find and compare flights from Watertown, New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 3/24

4:01 pm-9:18 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 3/28

4:48 pm-10:55 pm

1 stop5h 07m

$298

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 3/24

4:01 pm-12:06 am

2 stops9h 05m

Chicago O'Hare Intl

Sat 3/28

4:48 pm-10:55 pm

1 stop5h 07m

$304

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 7/31

4:09 pm-9:45 pm

1 stop6h 36m

Chicago O'Hare Intl

Tue 8/4

9:45 am-3:44 pm

1 stop4h 59m

$411

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 3/24

4:01 pm-12:06 am

2 stops9h 05m

Chicago O'Hare Intl

Sat 3/28

1:39 pm-10:55 pm

2 stops8h 16m

$416

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/26

6:00 am-12:35 pm

2 stops7h 35m

Chicago O'Hare Intl

Sun 3/29

8:23 am-3:19 pm

1 stop5h 56m

$423

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/26

6:00 am-10:12 am

1 stop5h 12m

Chicago O'Hare Intl

Mon 3/30

8:23 am-3:19 pm

1 stop5h 56m

$437

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 3/26

6:00 am-12:16 pm

1 stop7h 16m

Chicago O'Hare Intl

Mon 3/30

1:39 pm-10:55 pm

2 stops8h 16m

$443
Quickest round-trip

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 5/22

4:06 pm-9:36 pm

1 stop6h 30m

Chicago O'Hare Intl

Mon 5/25

5:16 pm-10:52 pm

1 stop4h 36m

$517

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 5/22

4:06 pm-11:59 pm

2 stops8h 53m

Chicago O'Hare Intl

Mon 5/25

5:16 pm-10:52 pm

1 stop4h 36m

$522

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 7/31

4:09 pm-11:59 pm

2 stops8h 50m

Chicago O'Hare Intl

Tue 8/4

9:45 am-3:44 pm

1 stop4h 59m

$531

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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

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?

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

What airlines fly to Chicago?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Watertown, New York according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Watertown, New York to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Watertown, New York to Chicago 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 (ART to CHI) flight deals and tips

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

Fastest flight time

5h 12m

Direct flights

None
The fastest flight from Watertown, New York to Chicago takes 5h 12m
There are no direct flights from Watertown, New York to Chicago. There are no popular flight routes from Watertown, New York to Chicago.
Search flight deals

  • How far is Watertown to Chicago by plane?

    The straight-line distance from Watertown to Chicago is 609.3 mi. Typically, this will take 5h 12m by plane in normal conditions.

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

    Prices for flights from Watertown Airport to Chicago are refreshed on a daily basis.

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

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Watertown to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Chicago from Watertown with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Watertown.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport