$186 Cheap Flights from Watertown (ATY) to Chicago (ORD)

View $186 flight on Thu, Dec 25, 2025Opens in a new window

Popular airlines from Watertown, SD (ATY-Watertown Regional) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Watertown to Chicago (ATY-ORD)

Prices were available within the past 7 days and start at $186 for one-way flights and $234 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Dec 30 - Sun, Jan 11
ATY
Watertown
ORD
Chicago
$234 Roundtrip, found 14 hours ago
$234
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Dec 30 from Watertown to Chicago, returning Sun, Jan 11, priced at $234 found 14 hours ago
Delta
Tue, Dec 30 - Fri, Jan 9
ATY
Watertown
ORD
Chicago
$244 Roundtrip, found 14 hours ago
$244
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Dec 30 from Watertown to Chicago, returning Fri, Jan 9, priced at $244 found 14 hours ago
Delta
Sat, Dec 27 - Wed, Dec 31
ATY
Watertown
ORD
Chicago
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 27 from Watertown to Chicago, returning Wed, Dec 31, priced at $249 found 1 day ago
Delta
Thu, Dec 25 - Thu, Jan 1
ATY
Watertown
ORD
Chicago
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Dec 25 from Watertown to Chicago, returning Thu, Jan 1, priced at $259 found 1 day ago
Delta
Sat, Dec 13 - Tue, Dec 16
ATY
Watertown
ORD
Chicago
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 13 from Watertown to Chicago, returning Tue, Dec 16, priced at $264 found 1 day ago
Delta
Tue, Dec 9 - Fri, Dec 19
ATY
Watertown
ORD
Chicago
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Dec 9 from Watertown to Chicago, returning Fri, Dec 19, priced at $279 found 3 days ago
Delta
Thu, Dec 11 - Sat, Dec 13
ATY
Watertown
ORD
Chicago
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Dec 11 from Watertown to Chicago, returning Sat, Dec 13, priced at $294 found 1 day ago
Delta
Tue, Dec 30 - Sat, Jan 17
ATY
Watertown
ORD
Chicago
$299 Roundtrip, found 14 hours ago
$299
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Dec 30 from Watertown to Chicago, returning Sat, Jan 17, priced at $299 found 14 hours ago
Delta
Thu, Jan 29 - Sun, Feb 1
ATY
Watertown
ORD
Chicago
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 29 from Watertown to Chicago, returning Sun, Feb 1, priced at $304 found 1 day ago
United
Mon, Jan 26 - Sat, Feb 7
ATY
Watertown
ORD
Chicago
$472 Roundtrip, found 6 days ago
$472
Roundtrip
found 6 days ago
Select United flight, departing Mon, Jan 26 from Watertown to Chicago, returning Sat, Feb 7, priced at $472 found 6 days ago

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Find the cheapest month to fly from Watertown (ATY) to Chicago (ORD)

February is typically the cheapest month to fly

From $148 - $504 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $344
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $344
Flights from Watertown (ATY) to Chicago (ORD)
Origin airport
Watertown Regional
Destination airport
O'Hare Intl.
Airlines serving
Delta, United
Roundtrip price
$233
Distance
506 mi

Watertown to Chicago Flights

The cheapest times to fly from Watertown to Chicago

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 Watertown to Chicago are during the month of December. You can find some of the cheapest flights from Watertown to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Watertown to Chicago

Sunday is one of the best days to book for cheap flights from Watertown to Chicago: 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 Watertown to Chicago

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 Watertown to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $186 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 Watertown to Chicago 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 Watertown to Chicago 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 Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight from $186 or cheap return flight from $234 from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from ATY to ORD is December, when demand is low. Off-peak months are usually when better flight deals are available between these airports.
Which airlines fly direct from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
If you're departing from Watertown Regional Airport (ATY), you can catch a nonstop flight to O'Hare Intl. Airport (ORD) with Denver Air Connection.
What is the cheapest airline that flies from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from ATY to ORD, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
On average, you can choose from 6 direct flights each week from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD). For greater flexibility, consider taking a flight with a layover. Just enter your details on Expedia and then filter your search to include one stop or more.
What are the most popular departure times for flights from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
More passengers fly between ATY and ORD at 8 AM than at any other time of day. Looking for a quieter experience? Try choosing a quieter departure window and there's a chance you'll save on your fare as well.
What day of the week has the most flights from ATY to ORD?
Depart on a Saturday if you're looking for the largest selection of flights from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
The first flight of the day leaving from Watertown Regional Airport (ATY) is at around 8:45AM UTC-6. Board this plane and you'll land at O'Hare Intl. Airport (ORD) at approximately 10:25AM UTC-6. The overall travel time is 1h 40m.
How long does it take to fly from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
It takes about 1 hour and 40 minutes to fly the 510 mi from ATY to ORD.
What is the best time to fly from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the likelihood of delays. Departures after this time have a 22% higher chance of being canceled, on average.**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 Chicago from Watertown Regional Airport (ATY)?
If you're flying on a direct flight from Watertown Regional Airport (ATY) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from ATY to ORD right before your getaway is usually more expensive. But if there's some wiggle room with your itinerary, you could bag a cheap last-minute fare.
Is it cheaper to book an ATY to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking an ATY to ORD flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place takes the hassle out of planning your trip. Just pick your flights and choose from our extensive range of hotels, then tailor your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from Watertown Regional Airport (ATY) to O'Hare Intl. Airport (ORD)?
In most instances, you can cancel or reschedule your ATY to ORD flight. However, additional charges may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you want more information, go to our Customer Service portal.

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*Available to One Key members.