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ART - ORD

Find cheap flights from Watertown to Chicago from $255

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Watertown to Chicago departing on 6/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 5/24
Fri 5/31

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Watertown to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Watertown to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Watertown to Chicago (ART-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Watertown to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:44 pm - 10:33 pmART-ORD
4h 49m1 stop
9:57 am - 6:19 pmORD-ART
7h 22m1 stop
$450American Airlines
Find Deal
Tue, May 28 - Sun, Jun 2
6:36 am - 11:56 amART-ORD
6h 20m1 stop
4:50 pm - 10:11 pmORD-ART
4h 21m1 stop
$470American Airlines
Find Deal
Thu, Sep 12 - Mon, Sep 16
4:36 pm - 11:36 pmART-ORD
8h 00m2 stops
6:54 am - 3:02 pmORD-ART
7h 08m1 stop
$475American Airlines
Find Deal
Thu, Sep 12 - Mon, Sep 16
6:36 am - 12:09 pmART-ORD
6h 33m2 stops
8:20 am - 3:02 pmORD-ART
5h 42m2 stops
$480American Airlines
Find Deal
Thu, Sep 12 - Mon, Sep 16
6:44 pm - 10:33 pmART-ORD
4h 49m1 stop
12:13 pm - 10:28 pmORD-ART
9h 15m2 stops
$527American Airlines
Find Deal
Tue, May 28 - Sun, Jun 2
6:03 am - 10:42 amART-ORD
5h 39m1 stop
4:55 pm - 10:43 pmORD-ART
4h 48m1 stop
$535American Airlines
Find Deal
Sat, Jun 29 - Sun, Jun 30
6:03 am - 2:10 pmART-ORD
9h 07m2 stops
4:55 pm - 10:43 pmORD-ART
4h 48m1 stop
$560American Airlines
Find Deal
Sat, Jun 29 - Sun, Jun 30
6:44 pm - 10:33 pmART-ORD
4h 49m1 stop
11:54 am - 6:19 pmORD-ART
5h 25m1 stop
$570American Airlines
Find Deal
Thu, May 9 - Sat, May 11
6:44 pm - 10:33 pmART-ORD
4h 49m1 stop
12:15 pm - 10:28 pmORD-ART
9h 13m2 stops
$573American Airlines
Find Deal
Thu, May 9 - Sat, May 11
6:15 am - 2:20 pmART-ORD
9h 05m2 stops
9:57 am - 6:19 pmORD-ART
7h 22m1 stop
$575American Airlines
Find Deal
Fri, May 10 - Mon, May 20

Flights from Watertown to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Watertown to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Watertown to Chicago?

The average price of all flights from Watertown, New York to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Watertown to Chicago. For your return ticket, we recommend flying on a Monday and avoiding Wednesdays for the best deals.

Good to know

Cheapest flight

$255
Flight from Watertown to Chicago

When to book flights from Watertown to Chicago

Are your dates flexible? Find out the best times to travel from Watertown to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Watertown to Chicago flights

  • What is the cheapest flight from Watertown, New York to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Watertown, New York to Chicago O'Hare Intl Airport was $255 for a one-way ticket and $450 for a round-trip.

  • Do I need a passport to fly between Watertown and Chicago?

    A passport is not required to fly from Watertown to Chicago.

  • Which aircraft models fly most regularly from Watertown to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Watertown to Chicago?

    oneworld is the only airline alliance operating flights between Watertown and Chicago.

  • How does KAYAK find such low prices on flights from Watertown to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Watertown to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Watertown to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Watertown is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Watertown to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Watertown with another airline. Booking your flights between Watertown and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Watertown to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Watertown up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Watertown to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Watertown to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Watertown to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
American AirlinesOverall score based on 14898 reviews
7.2comfort
6.6food
7.1entertainment
7.6boarding
8.0crew
Airline reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

6.0 GoodAnonymous, Apr 2024SPI - ORD
Read more about American Airlines reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from Watertown to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Watertown to Chicago found on KAYAK in the last 72 hours.
6/29Sat
1 stopAmerican Airlines
5h 39mART-ORD
$255
6/29Sat
2 stopsAmerican Airlines
7h 12mART-ORD
$260

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Watertown - Chicago Flights

Departure:

Watertown (ART)United States

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Watertown

Cabin classes: