$89 Cheap Flights from Chicago (ORD) to Watertown (ATY)

View $89 flight on Mon, Jun 2, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Watertown (ORD-ATY)

Prices were available within the past 7 days and start at $89 for one-way flights and $178 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, May 23 - Sun, May 25
ORD
Chicago
ATY
Watertown
$178 Roundtrip, found 1 hour ago
$178
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, May 23 from Chicago to Watertown, returning Sun, May 25, priced at $178 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Jul 10 - Thu, Jul 17
ORD
Chicago
ATY
Watertown
$198 Roundtrip, found 19 hours ago
$198
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 10 from Chicago to Watertown, returning Thu, Jul 17, priced at $198 found 19 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Jun 2 - Thu, Jun 5
ORD
Chicago
ATY
Watertown
$218 Roundtrip, found 8 hours ago
$218
Roundtrip
found 8 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Jun 2 from Chicago to Watertown, returning Thu, Jun 5, priced at $218 found 8 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Jun 1 - Thu, Jun 5
ORD
Chicago
ATY
Watertown
$238 Roundtrip, found 8 hours ago
$238
Roundtrip
found 8 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Jun 1 from Chicago to Watertown, returning Thu, Jun 5, priced at $238 found 8 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, May 1 - Fri, May 2
ORD
Chicago
ATY
Watertown
$258 Roundtrip, found 11 hours ago
$258
Roundtrip
found 11 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, May 1 from Chicago to Watertown, returning Fri, May 2, priced at $258 found 11 hours ago
American Airlines
Wed, Jun 4 - Fri, Jun 13
ORD
Chicago
ATY
Watertown
$273 Roundtrip, found 3 days ago
$273
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 4 from Chicago to Watertown, returning Fri, Jun 13, priced at $273 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Apr 29 - Fri, May 2
ORD
Chicago
ATY
Watertown
$278 Roundtrip, found 11 hours ago
$278
Roundtrip
found 11 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Apr 29 from Chicago to Watertown, returning Fri, May 2, priced at $278 found 11 hours ago
American Airlines
Wed, Jun 25 - Fri, Jul 4
ORD
Chicago
ATY
Watertown
$282 Roundtrip, found 2 days ago
$282
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jun 25 from Chicago to Watertown, returning Fri, Jul 4, priced at $282 found 2 days ago
American Airlines
Wed, May 21 - Thu, May 22
ORD
Chicago
ATY
Watertown
$283 Roundtrip, found 5 hours ago
$283
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, May 21 from Chicago to Watertown, returning Thu, May 22, priced at $283 found 5 hours ago
United
Tue, Aug 5 - Tue, Aug 19
ORD
Chicago
ATY
Watertown
$459 Roundtrip, found 1 day ago
$459
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 5 from Chicago to Watertown, returning Tue, Aug 19, priced at $459 found 1 day ago
Flights from Chicago (ORD) to Watertown (ATY)
Origin airport
O'Hare Intl.
Destination airport
Watertown Regional
Airlines serving
KEY LIME AIR DBA DENVER AIR CONNECTION, United
Roundtrip price
$178
Distance
506 mi

Chicago to Watertown Flights

The cheapest times to fly from Chicago to Watertown

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Watertown are during the month of May. You can find some of the cheapest flights from Chicago to Watertown with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Watertown

Sunday is one of the best days to book for cheap flights from Chicago to Watertown: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Watertown

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Watertown in 2025. You can also book with separate airlines for your outbound and return journeys, from $89 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Watertown flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Watertown airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY) cost?
Pick up cheap return tickets starting at $178 from O’Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Key Lime DBA Denver Air Connection flight leaving ORD on May 16 2025 and touching down at ATY. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from ORD to ATY?
The cheapest flights from ORD to ATY are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY)?
Fly nonstop from O’Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY) on a Denver Air Connection flight.
What is the cheapest airline that flies from ORD to ATY?
Jet off from ORD to ATY with Key Lime DBA Denver Air Connection. This airline currently has the cheapest one-way fare on this route, starting at $89. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on June 24 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY)?
On average, you can take your pick of 6 direct flights taking off from O’Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY) every week. If you can’t find one that fits your travel plans, think about a flight with a layover. Filter your search on Expedia to include one stop or more and opt for the next best alternative.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY)?
The 1 PM departures from ORD to ATY are typically the busiest. Prices can be higher for these popular slots. If you’re hoping to save money, choose a less crowded time to fly.
What day of the week has the most flights from ORD to ATY?
Jet off on a Sunday if you’re after the biggest selection of flights from O’Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY)?
O’Hare Intl. Airport (ORD)’s earliest flight to Watertown Regional Airport (ATY) leaves at approximately 1:40PM UTC-6. With a travel time of 1h 40m, you’ll land at around 3:20PM UTC-6.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY)?
The average flight duration from ORD to ATY is 1 hour and 40 minutes, covering a distance of 510 mi.
What airline has the least delays from ORD to ATY?
With 86% of journeys usually arriving on schedule, United Airlines has the best on-time performance for direct flights from O’Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY). To monitor your flight status and get notifications if anything changes, head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY) route, fly before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Watertown from O'Hare Intl. Airport (ORD)?
Watertown Regional Airport (ATY) is the only airport in Watertown with direct flights from O’Hare Intl. Airport (ORD). Check out the available options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY) last-minute?
Booking your plane ticket from ORD to ATY right before your journey is generally more expensive. However, if there’s some wiggle room with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book an ORD to ATY flight and hotel package?
Opting for an ORD to ATY flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Select from our extensive range of stays and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Watertown Regional Airport (ATY)?
In most instances, you can modify or cancel your ORD to ATY flight. However, additional charges may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline’s guidelines and fees on flight changes, or if you’d like more information, go to our Customer Service portal.

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