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Cheap flights from Watertown, New York to Chicago from $445

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 10/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

American Airlines Logo
2:45 pm - 8:11 pmART-ORD
6h 26m1 stop
American Airlines Logo
8:45 am - 1:59 pmORD-ART
4h 14m1 stop
$445American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
2:45 pm - 8:11 pmART-ORD
6h 26m1 stop
American Airlines Logo
5:20 am - 1:59 pmORD-ART
7h 39m2 stops
$451American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
6:00 am - 12:03 pmART-ORD
7h 03m2 stops
American Airlines Logo
5:20 am - 1:59 pmORD-ART
7h 39m2 stops
$482American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
6:00 am - 12:03 pmART-ORD
7h 03m2 stops
American Airlines Logo
5:20 am - 1:59 pmORD-ART
7h 39m2 stops
$618American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
2:26 pm - 10:39 pmART-ORD
9h 13m1 stop
American Airlines Logo
8:45 am - 2:20 pmORD-ART
4h 35m1 stop
$838American Airlines
Find Deal
Tue, Oct 7 - Fri, Oct 10
American Airlines Logo
6:00 am - 8:11 pmART-ORD
15h 11m1 stop
American Airlines Logo
5:22 am - 2:20 pmORD-ART
7h 58m2 stops
$843American Airlines
Find Deal
Tue, Oct 7 - Fri, Oct 10
American Airlines Logo
6:00 am - 1:11 pmART-ORD
8h 11m2 stops
American Airlines Logo
5:22 am - 2:20 pmORD-ART
7h 58m2 stops
$884American Airlines
Find Deal
Tue, Oct 7 - Fri, Oct 10
American Airlines Logo
6:00 am - 12:20 pmART-ORD
7h 20m1 stop
American Airlines Logo
9:55 am - 4:02 pmORD-ART
5h 07m1 stop
$920American Airlines
Find Deal
Mon, Sep 22 - Fri, Sep 26
American Airlines Logo
4:27 pm - 11:48 pmART-ORD
8h 21m2 stops
American Airlines Logo
8:35 am - 4:02 pmORD-ART
6h 27m1 stop
$926American Airlines
Find Deal
Mon, Sep 22 - Fri, Sep 26

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
Oct 10
ART2:45 pmWatertown
6h 26m
1 stop
ORD8:11 pmChicago O'Hare Intl
Oct 14
ORD8:45 amChicago O'Hare Intl
4h 14m
1 stop
ART1:59 pmWatertown
$445
Find similar
American Airlines
Oct 10
ART2:45 pmWatertown
6h 26m
1 stop
ORD8:11 pmChicago O'Hare Intl
Oct 14
ORD5:20 amChicago O'Hare Intl
7h 39m
2 stops
ART1:59 pmWatertown
$451
Find similar
American Airlines
Oct 10
ART6:00 amWatertown
7h 03m
2 stops
ORD12:03 pmChicago O'Hare Intl
Oct 14
ORD5:20 amChicago O'Hare Intl
7h 39m
2 stops
ART1:59 pmWatertown
$482
Find similar

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 September 9, 2025.
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

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 10/10

2:45 pm-8:11 pm

1 stop6h 26m

Chicago O'Hare Intl

Tue 10/14

8:45 am-1:59 pm

1 stop4h 14m

$445

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 10/10

2:45 pm-8:11 pm

1 stop6h 26m

Chicago O'Hare Intl

Tue 10/14

5:20 am-1:59 pm

2 stops7h 39m

$451

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 10/10

6:00 am-12:03 pm

2 stops7h 03m

Chicago O'Hare Intl

Tue 10/14

5:20 am-1:59 pm

2 stops7h 39m

$482

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 10/10

6:00 am-12:03 pm

2 stops7h 03m

Chicago O'Hare Intl

Tue 10/14

5:20 am-1:59 pm

2 stops7h 39m

$618

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 10/7

2:26 pm-10:39 pm

1 stop9h 13m

Chicago O'Hare Intl

Fri 10/10

8:45 am-2:20 pm

1 stop4h 35m

$838

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 10/7

6:00 am-8:11 pm

1 stop15h 11m

Chicago O'Hare Intl

Fri 10/10

5:22 am-2:20 pm

2 stops7h 58m

$843

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 10/7

6:00 am-1:11 pm

2 stops8h 11m

Chicago O'Hare Intl

Fri 10/10

5:22 am-2:20 pm

2 stops7h 58m

$884

WatertownChicago

ART - ORD

ARTORD

Watertown

Mon 9/22

6:00 am-12:20 pm

1 stop7h 20m

Chicago O'Hare Intl

Fri 9/26

9:55 am-4:02 pm

1 stop5h 07m

$920

WatertownChicago

ART - ORD

ARTORD

Watertown

Mon 9/22

4:27 pm-11:48 pm

2 stops8h 21m

Chicago O'Hare Intl

Fri 9/26

8:35 am-4:02 pm

1 stop6h 27m

$926

WatertownChicago

ART - ORD

ARTORD

Watertown

Fri 10/10

2:45 pm-8:11 pm

1 stop6h 26m

$460

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 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

What airlines fly to Chicago O'Hare Intl Airport?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Watertown, New York according to our data. American Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

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

Direct flights

None
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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  • 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. 6h 26m 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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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