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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 5/9. 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

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 - 12:18 pm
ART
-
ORD
7h 18m
1 stop
American Airlines Logo
5:00 am - 10:59 am
ORD
-
ART
4h 59m
1 stop
$318American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
11:25 am - 7:22 pm
ART
-
ORD
8h 57m
2 stops
American Airlines Logo
3:29 pm - 11:23 pm
ORD
-
ART
6h 54m
1 stop
$324American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
11:25 am - 5:58 pm
ART
-
ORD
7h 33m
2 stops
American Airlines Logo
5:00 am - 10:59 am
ORD
-
ART
4h 59m
1 stop
$384American Airlines
Thu, May 14 - Sun, May 17
American Airlines Logo
6:00 am - 11:38 am
ART
-
ORD
6h 38m
1 stop
American Airlines Logo
5:00 am - 10:59 am
ORD
-
ART
4h 59m
1 stop
$425American Airlines
Wed, May 13 - Sun, May 17
American Airlines Logo
11:25 am - 5:58 pm
ART
-
ORD
7h 33m
2 stops
American Airlines Logo
1:54 pm - 11:23 pm
ORD
-
ART
8h 29m
2 stops
$436American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
6:00 am - 12:18 pm
ART
-
ORD
7h 18m
1 stop
American Airlines Logo
5:00 am - 10:59 am
ORD
-
ART
4h 59m
1 stop
$488American Airlines
Thu, May 14 - Sat, May 16
American Airlines Logo
11:25 am - 5:58 pm
ART
-
ORD
7h 33m
2 stops
American Airlines Logo
11:15 am - 11:28 pm
ORD
-
ART
11h 13m
2 stops
$494American Airlines
Thu, May 14 - Sat, May 16
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
$530American Airlines
Fri, May 15 - Sun, May 17
American Airlines Logo
4:06 pm - 11:58 pm
ART
-
ORD
8h 52m
2 stops
American Airlines Logo
6:55 am - 3:39 pm
ORD
-
ART
7h 44m
2 stops
$541American Airlines
Fri, Jun 5 - Fri, Jun 12
American Airlines Logo
4:21 pm - 9:00 pm
ART
-
ORD
5h 39m
1 stop
American Airlines Logo
6:55 am - 3:39 pm
ORD
-
ART
7h 44m
2 stops
$573American Airlines
Sat, Jun 20 - Mon, Jun 22

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American Airlines flights from Watertown, New York to Chicago

Our best American Airlines deals on Watertown, New York to Chicago flight tickets
American Airlines
May 9
ART6:00 amWatertown
7h 18m
1 stop
ORD12:18 pmChicago O'Hare Intl
May 13
ORD5:00 amChicago O'Hare Intl
4h 59m
1 stop
ART10:59 amWatertown
$318
American Airlines
May 9
ART11:25 amWatertown
8h 57m
2 stops
ORD7:22 pmChicago O'Hare Intl
May 13
ORD3:29 pmChicago O'Hare Intl
6h 54m
1 stop
ART11:23 pmWatertown
$324
American Airlines
May 14
ART11:25 amWatertown
7h 33m
2 stops
ORD5:58 pmChicago O'Hare Intl
May 17
ORD5:00 amChicago O'Hare Intl
4h 59m
1 stop
ART10:59 amWatertown
$384

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 April 28, 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

Sat 5/9

6:00 am-12:18 pm

1 stop7h 18m

Chicago O'Hare Intl

Wed 5/13

5:00 am-10:59 am

1 stop4h 59m

$318

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 5/9

11:25 am-7:22 pm

2 stops8h 57m

Chicago O'Hare Intl

Wed 5/13

3:29 pm-11:23 pm

1 stop6h 54m

$324

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 5/14

11:25 am-5:58 pm

2 stops7h 33m

Chicago O'Hare Intl

Sun 5/17

5:00 am-10:59 am

1 stop4h 59m

$384

WatertownChicago

ART - ORD

ARTORD

Watertown

Wed 5/13

6:00 am-11:38 am

1 stop6h 38m

Chicago O'Hare Intl

Sun 5/17

5:00 am-10:59 am

1 stop4h 59m

$425

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 5/9

11:25 am-5:58 pm

2 stops7h 33m

Chicago O'Hare Intl

Wed 5/13

1:54 pm-11:23 pm

2 stops8h 29m

$436

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 5/14

6:00 am-12:18 pm

1 stop7h 18m

Chicago O'Hare Intl

Sat 5/16

5:00 am-10:59 am

1 stop4h 59m

$488

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 5/14

11:25 am-5:58 pm

2 stops7h 33m

Chicago O'Hare Intl

Sat 5/16

11:15 am-11:28 pm

2 stops11h 13m

$494
Quickest round-trip

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 5/15

6:00 am-10:41 am

1 stop5h 41m

Chicago O'Hare Intl

Sun 5/17

5:00 am-10:59 am

1 stop4h 59m

$530

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 6/5

4:06 pm-11:58 pm

2 stops8h 52m

Chicago O'Hare Intl

Fri 6/12

6:55 am-3:39 pm

2 stops7h 44m

$541

WatertownChicago

ART - ORD

ARTORD

Watertown

Sat 6/20

4:21 pm-9:00 pm

1 stop5h 39m

Chicago O'Hare Intl

Mon 6/22

6:55 am-3:39 pm

2 stops7h 44m

$573

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

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 59% 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

6h 38m

Direct flights

None
The fastest flight from Watertown, New York to Chicago takes 6h 38m
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

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

  • How far is Watertown to Chicago by plane?

    The straight-line distance from Watertown to Chicago is 609.3 mi. Typically, this will take 6h 38m 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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