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Cheap flights from Watertown, New York to Chicago from $291

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
5:25 pm - 10:30 pmART  Watertown-ORD Chicago O'Hare Intl
6h 05m1 stop Philadelphia
American Airlines Logo
3:37 pm - 10:27 pmORD  Chicago O'Hare Intl-ART Watertown
5h 50m1 stop Philadelphia
$574American Airlines
Thu, Oct 15 - Mon, Oct 19
American Airlines Logo
5:25 pm - 10:30 pmART  Watertown-ORD Chicago O'Hare Intl
6h 05m1 stop Philadelphia
American Airlines Logo
3:21 pm - 10:55 pmORD  Chicago O'Hare Intl-ART Watertown
6h 34m1 stop Philadelphia
$574American Airlines
Fri, Oct 30 - Sun, Nov 1
American Airlines Logo
5:25 pm - 5:49 amART  Watertown-ORD Chicago O'Hare Intl
13h 24m2 stops Philadelphia Cleveland Hopkins Intl
American Airlines Logo
3:37 pm - 10:27 pmORD  Chicago O'Hare Intl-ART Watertown
5h 50m1 stop Philadelphia
$577American Airlines
Thu, Oct 15 - Mon, Oct 19
American Airlines Logo
4:24 pm - 9:30 pmART  Watertown-ORD Chicago O'Hare Intl
6h 06m1 stop Philadelphia
American Airlines Logo
8:45 am - 3:53 pmORD  Chicago O'Hare Intl-ART Watertown
6h 08m1 stop Philadelphia
$613American Airlines
Wed, Sep 23 - Sun, Sep 27
American Airlines Logo
6:00 am - 10:56 amART  Watertown-ORD Chicago O'Hare Intl
5h 56m1 stop Philadelphia
American Airlines Logo
6:00 am - 3:59 pmORD  Chicago O'Hare Intl-ART Watertown
8h 59m2 stops Boston Logan Intl Philadelphia
$686American Airlines
Fri, Sep 25 - Tue, Sep 29
American Airlines Logo
4:24 pm - 11:36 pmART  Watertown-ORD Chicago O'Hare Intl
8h 12m2 stops Philadelphia Washington, D.C. Reagan-National
American Airlines Logo
4:54 pm - 10:50 pmORD  Chicago O'Hare Intl-ART Watertown
4h 56m1 stop Philadelphia
$686American Airlines
Wed, Sep 23 - Sun, Sep 27
American Airlines Logo
6:00 am - 2:20 pmART  Watertown-ORD Chicago O'Hare Intl
9h 20m2 stops Philadelphia Charlotte Douglas
American Airlines Logo
3:21 pm - 10:55 pmORD  Chicago O'Hare Intl-ART Watertown
6h 34m1 stop Philadelphia
$714American Airlines
Fri, Oct 30 - Sun, Nov 1
American Airlines Logo
5:25 pm - 5:49 amART  Watertown-ORD Chicago O'Hare Intl
13h 24m2 stops Philadelphia Cleveland Hopkins Intl
American Airlines Logo
8:40 am - 5:00 pmORD  Chicago O'Hare Intl-ART Watertown
7h 20m2 stops Washington, D.C. Reagan-National Philadelphia
$716American Airlines
Thu, Oct 15 - Mon, Oct 19
American Airlines Logo
6:00 am - 12:24 pmART  Watertown-ORD Chicago O'Hare Intl
7h 24m1 stop Philadelphia
American Airlines Logo
5:29 pm - 10:56 pmORD  Chicago O'Hare Intl-ART Watertown
4h 27m1 stop Philadelphia
$719American Airlines
Thu, Nov 19 - Mon, Nov 30
American Airlines Logo
4:24 pm - 11:59 pmART  Watertown-ORD Chicago O'Hare Intl
8h 35m2 stops Philadelphia Charlotte Douglas
American Airlines Logo
6:45 am - 3:53 pmORD  Chicago O'Hare Intl-ART Watertown
8h 08m2 stops Charlotte Douglas Philadelphia
$788American Airlines
Wed, Sep 23 - Sun, Sep 27

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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
Oct 15
ART5:25 pmWatertown
6h 05m
1 stop
ORD10:30 pmChicago O'Hare Intl
Oct 19
ORD3:37 pmChicago O'Hare Intl
5h 50m
1 stop
ART10:27 pmWatertown
$574
American Airlines
Oct 15
ART5:25 pmWatertown
13h 24m
2 stops
ORD5:49 amChicago O'Hare Intl
Oct 19
ORD3:37 pmChicago O'Hare Intl
5h 50m
1 stop
ART10:27 pmWatertown
$577
American Airlines
Sep 23
ART4:24 pmWatertown
6h 06m
1 stop
ORD9:30 pmChicago O'Hare Intl
Sep 27
ORD8:45 amChicago O'Hare Intl
6h 08m
1 stop
ART3:53 pmWatertown
$613

momondo Fare Finder

 
Use the filters below to find and compare flights from Watertown, New York to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Thu 10/15

5:25 pm-10:30 pm

1 stop6h 05m

Chicago O'Hare Intl

Mon 10/19

3:37 pm-10:27 pm

1 stop5h 50m

$574

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Fri 10/30

5:25 pm-10:30 pm

1 stop6h 05m

Chicago O'Hare Intl

Sun 11/1

3:21 pm-10:55 pm

1 stop6h 34m

$574

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Thu 10/15

5:25 pm-5:49 am

2 stops13h 24m

Chicago O'Hare Intl

Mon 10/19

3:37 pm-10:27 pm

1 stop5h 50m

$577

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Wed 9/23

4:24 pm-9:30 pm

1 stop6h 06m

Chicago O'Hare Intl

Sun 9/27

8:45 am-3:53 pm

1 stop6h 08m

$613

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Fri 9/25

6:00 am-10:56 am

1 stop5h 56m

Chicago O'Hare Intl

Tue 9/29

6:00 am-3:59 pm

2 stops8h 59m

$686

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Wed 9/23

4:24 pm-11:36 pm

2 stops8h 12m

Chicago O'Hare Intl

Sun 9/27

4:54 pm-10:50 pm

1 stop4h 56m

$686

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Fri 10/30

6:00 am-2:20 pm

2 stops9h 20m

Chicago O'Hare Intl

Sun 11/1

3:21 pm-10:55 pm

1 stop6h 34m

$714

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Thu 10/15

5:25 pm-5:49 am

2 stops13h 24m

Chicago O'Hare Intl

Mon 10/19

8:40 am-5:00 pm

2 stops7h 20m

$716
Quickest round-trip

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Thu 11/19

6:00 am-12:24 pm

1 stop7h 24m

Chicago O'Hare Intl

Mon 11/30

5:29 pm-10:56 pm

1 stop4h 27m

$719

WatertownChicago

ART Watertown - ORD Chicago O'Hare Intl

ARTORD

Watertown

Wed 9/23

4:24 pm-11:59 pm

2 stops8h 35m

Chicago O'Hare Intl

Sun 9/27

6:45 am-3:53 pm

2 stops8h 08m

$788

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 58% 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

Best Price Found

$291

Fastest flight time

5h 56m

Direct flights

None
The best one-way flight to Chicago from Watertown, New York in the past 72 hours is $291. The best round-trip flight deal from Watertown, New York to Chicago found on momondo in the last 72 hours is $574.
The fastest flight from Watertown, New York to Chicago takes 5h 56m
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 5h 56m 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport