ATY - CHI

Find cheap flights from Watertown to Chicago

1 adult
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Watertown to Chicago (ATY-CHI)

 
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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Watertown to Chicago

Multiple Airlines Logo
ATY-CHI
522 mimulti-stop
Multiple Airlines Logo
CHI-ATY
522 mimulti-stop
Multiple Airlines
Find Deal

Everything you should know

Top routes
ATY-ORD
Cheapest
ATY-ORD
Most popular
Insights
Insights
Insights
Insights
Cheapest round-trip
Multiple Airlines
Mon 10/27
ATY - CHI • multi-stop
Cheapest one-way
Multiple Airlines
Mon 10/27
ATY - CHI • multi-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for Watertown to Chicago flights

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 is the cheapest Watertown to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Watertown to Chicago costs $164 on the route between Watertown (ATY) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

The average price of all round-trip flights from Watertown to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Watertown to Chicago, look for departures on Sundays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Chicago, Saturday is the cheapest day to fly and Friday is the most expensive.

Can I save money by flying with a layover from Watertown to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $164, prices are generally cheapest when you fly direct.

Find deals

Good to know

Most popular time to fly and prices are also 11% lower on average.

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 flights from Watertown to Chicago

  • 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?

    The Embraer ERJ-145 is the aircraft model that flies most regularly on the Watertown to Chicago flight route.

  • 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.

  • 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.

Reviews of the 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.
8.7
Denver Air ConnectionOverall score based on 19 reviews
8.4Food
8.9Comfort
8.1Entertainment
8.7Boarding
9.4Crew
Airline reviews

Communication with delays. Failed to make a connection I ng flight in Chicago.

2.0 MediocreAnonymous, Oct 2025IWD - ORD
Read more Denver Air Connection reviews

Communication with delays. Failed to make a connection I ng flight in Chicago.

Excellent, from check Iin to arrival. I was apprehensive about flying a small plane between Ironwood and Chicago, but the flight and service was great. I noticed, after boarding , that my cell phone had little battery left. The flight attendant kindly lent me a charging device to keep me connected with my contact in Chicago upon landing. I will always remember that kindness.

Great snacks and friendly people for check in at Pierre SD!

The connecting flight came in 45 min late but everything else was great

Absolutely easy travels and no cost cutting by the airline.

Their snacks and hospitality was amazing. They offered full sized snacks. Im talking full sized water bottles, full sized snickers bars, gold fish, full sized canned sodas, what ever you wanted they took care of it for FREE. The crew was really nice and hospitable. I was honestly shocked

Everything you need to know for your flight from Watertown to Chicago

Information on your arrival and departure airports

Watertown (ATY)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.