$182 Cheap Flights from Chicago (MDW) to Watertown (ATY)

View $182 flight on Tue, Oct 21, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Watertown, SD (ATY-Watertown Regional)

Cheap Flights from Chicago to Watertown (MDW-ATY)

Prices were available within the past 7 days and start at $182 for one-way flights and $274 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Sep 24 - Sat, Sep 27
MDW
Chicago
ATY
Watertown
$274 Roundtrip, found 3 days ago
$274
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Watertown, returning Sat, Sep 27, priced at $274 found 3 days ago
Delta
Thu, Oct 30 - Sun, Nov 2
MDW
Chicago
ATY
Watertown
$319 Roundtrip, found 2 days ago
$319
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Oct 30 from Chicago to Watertown, returning Sun, Nov 2, priced at $319 found 2 days ago
Delta
Wed, Sep 24 - Sat, Sep 27
MDW
Chicago
ATY
Watertown
$324 Roundtrip, found 3 days ago
$324
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Watertown, returning Sat, Sep 27, priced at $324 found 3 days ago
Delta
Thu, Oct 30 - Wed, Nov 5
MDW
Chicago
ATY
Watertown
$340 Roundtrip, found 2 days ago
$340
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Oct 30 from Chicago to Watertown, returning Wed, Nov 5, priced at $340 found 2 days ago
Delta
Wed, Sep 24 - Sat, Sep 27
MDW
Chicago
ATY
Watertown
$350 Roundtrip, found 3 days ago
$350
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Watertown, returning Sat, Sep 27, priced at $350 found 3 days ago
Delta
Sat, Sep 20 - Tue, Sep 23
MDW
Chicago
ATY
Watertown
$356 Roundtrip, found 3 days ago
$356
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 20 from Chicago to Watertown, returning Tue, Sep 23, priced at $356 found 3 days ago
Delta
Tue, Aug 19 - Tue, Aug 26
MDW
Chicago
ATY
Watertown
$359 Roundtrip, found 5 days ago
$359
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Watertown, returning Tue, Aug 26, priced at $359 found 5 days ago
Delta
Tue, Aug 19 - Wed, Aug 27
MDW
Chicago
ATY
Watertown
$359 Roundtrip, found 6 days ago
$359
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Watertown, returning Wed, Aug 27, priced at $359 found 6 days ago
Delta
Sat, Aug 30 - Tue, Sep 9
MDW
Chicago
ATY
Watertown
$371 Roundtrip, found 1 day ago
$371
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 30 from Chicago to Watertown, returning Tue, Sep 9, priced at $371 found 1 day ago
Delta
Wed, Sep 24 - Sat, Sep 27
MDW
Chicago
ATY
Watertown
$374 Roundtrip, found 3 days ago
$374
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Watertown, returning Sat, Sep 27, priced at $374 found 3 days ago
Flights from Chicago (MDW) to Watertown (ATY)
Origin airport
Midway Intl.
Destination airport
Watertown Regional
Airlines serving
Delta
Roundtrip price
$273
Distance
520 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 September. 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 $182 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 Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY) cost?
Secure a cheap one-way flight from $182 or cheap return flight from $274 from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY)?
Planning your trip for September is a great way to save, as it's the cheapest month for flights between MDW and ATY. You'll usually find the lowest fares during off-peak months.
Which airlines fly direct from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY)?
You can't fly nonstop from Chicago, IL (MDW-Midway Intl.) to Watertown Regional Airport (ATY). However, you can easily travel to Watertown without any layovers by taking off from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY)?
To find the cheapest airline that'll fly you from MDW to ATY, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY)?
You'll need to catch a flight with a layover when traveling from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from MDW to ATY?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY)?
Opt for a flight from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY) that takes off before 3 PM to reduce the likelihood of delays and cancellations. 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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY) last-minute?
Booking your flight from MDW to ATY right before your journey is usually more expensive. However, if you're flexible with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to ATY flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to ATY flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place takes the hassle out of travel planning. Simply pick your flights and select from our wide range of hotels, then customize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Watertown Regional Airport (ATY)?
In most instances, you're able to cancel or reschedule your MDW to ATY flight. However, there may be additional fees, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you want more information, visit our Customer Service portal.

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*Available to One Key members.