Cheap Flights to Tripp County from $335 (2026/2027)

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Winner

Flights
Winner

How Much Does it Cost To Fly To Tripp County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, May 13 - Mon, May 17
ICT
Wichita Dwight D. Eisenhower National
PIR
Pierre Regional
$424 Roundtrip, found 1 day ago
$424
Roundtrip
found 1 day ago
Select United flight, departing Thu, May 13 from Wichita Dwight D. Eisenhower National to Pierre Regional, returning Mon, May 17, priced at $424 found 1 day ago
Thu, May 13 - Mon, May 17
ICT
Wichita Dwight D. Eisenhower National
PIR
Pierre Regional
$448 Roundtrip, found 11 hours ago
$448
Roundtrip
found 11 hours ago
Select United flight, departing Thu, May 13 from Wichita Dwight D. Eisenhower National to Pierre Regional, returning Mon, May 17, priced at $448 found 11 hours ago
Thu, May 13 - Mon, May 17
ICT
Wichita Dwight D. Eisenhower National
PIR
Pierre Regional
$470 Roundtrip, found 11 hours ago
$470
Roundtrip
found 11 hours ago
Select United flight, departing Thu, May 13 from Wichita Dwight D. Eisenhower National to Pierre Regional, returning Mon, May 17, priced at $470 found 11 hours ago
Thu, May 13 - Mon, May 17
ICT
Wichita Dwight D. Eisenhower National
PIR
Pierre Regional
$514 Roundtrip, found 1 day ago
$514
Roundtrip
found 1 day ago
Select United flight, departing Thu, May 13 from Wichita Dwight D. Eisenhower National to Pierre Regional, returning Mon, May 17, priced at $514 found 1 day ago
Thu, May 13 - Mon, May 17
ICT
Wichita Dwight D. Eisenhower National
PIR
Pierre Regional
$538 Roundtrip, found 11 hours ago
$538
Roundtrip
found 11 hours ago
Select United flight, departing Thu, May 13 from Wichita Dwight D. Eisenhower National to Pierre Regional, returning Mon, May 17, priced at $538 found 11 hours ago
Thu, May 13 - Mon, May 17
ICT
Wichita Dwight D. Eisenhower National
PIR
Pierre Regional
$549 Roundtrip, found 11 hours ago
$549
Roundtrip
found 11 hours ago
Select United flight, departing Thu, May 13 from Wichita Dwight D. Eisenhower National to Pierre Regional, returning Mon, May 17, priced at $549 found 11 hours ago
Sun, Feb 21 - Thu, Feb 25
MCI
Kansas City Intl.
PIR
Pierre Regional
$562 Roundtrip, found 6 hours ago
$562
Roundtrip
found 6 hours ago
Select United flight, departing Sun, Feb 21 from Kansas City Intl. to Pierre Regional, returning Thu, Feb 25, priced at $562 found 6 hours ago
Sun, Jun 6 - Fri, Jun 11
MCI
Kansas City Intl.
PIR
Pierre Regional
$604 Roundtrip, found 6 hours ago
$604
Roundtrip
found 6 hours ago
Select United flight, departing Sun, Jun 6 from Kansas City Intl. to Pierre Regional, returning Fri, Jun 11, priced at $604 found 6 hours ago

Travelers ❤️ These Tripp County 🏨

Holiday Inn Express & Suites Winner by IHG

Holiday Inn Express & Suites Winner by IHG

2.5 out of 5
1360 E Highway 44 Winner SD
Book a stay at this business-friendly hotel in Winner. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Tripp County Veteran’s Memorial and Winner City Pool are located nearby.
Opens in a new windowHoliday Inn Express & Suites Winner by IHG
Super 8 by Wyndham Winner SD

Super 8 by Wyndham Winner SD

2 out of 5
902 E Highway 44 Winner SD
Stay at this motel in Winner. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tripp County Veteran’s Memorial and Winner City Pool are located nearby.
7.8/10 Good! (355 reviews)
"The only problem we had was the coffee maker in the room did not work"

Reviewed on Nov 6, 2026

Opens in a new windowSuper 8 by Wyndham Winner SD
Warrior INN

Warrior INN

2 out of 5
845 SD-44 Winner SD
Stay at this motel in Winner. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Tripp County Veteran’s Memorial and Winner City Pool are located nearby.
Opens in a new windowWarrior INN
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Knights Inn Winner

Knights Inn Winner

1.5 out of 5
845 E. Highway 44 Winner SD
Stay at this motel in Winner. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Tripp County Veteran’s Memorial and Winner City Pool are located nearby.
5.2/10 (76 reviews)
Not worth a second stop.
"The staff was very friendly, but didn’t make up for the hotel. The most images online are fake and not what it really looks like. There was no sign outside annd the place looked closed. Most of the rooms were under renovation. One of our rooms did not have a chain lock or deadbolt and the shower ..."

Reviewed on Jul 1, 2025

Opens in a new windowKnights Inn Winner
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Tripp County?
Travelers scored a roundtrip flight to Tripp County for as little as $424 in the last seven days. If you find a bargain, grab it fast. Cheap deals don't hang around for long! This price was available on Travelocity for flights to Tripp County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Tripp County?
You can choose from 15 airline companies when you're ready to lock in your flight to Tripp County. Let Denver Air Connection fly you there comfortably. This popular carrier has 52 services every month to Winner, Tripp County's gateway city.
What is the cheapest month to fly to Tripp County?
For the best chance at grabbing an excellent flight deal, time your vacation during May. According to Travelocity's direct flight demand from January to December last year, it's the most affordable month to jet out to Tripp County.
How can I check my flight status to Tripp County?
"Trips" is your one-stop shop when it comes to details about your flight to Tripp County. Our handy portal allows you to manage everything in the one place, from checking the status of your flight to updating or canceling your booking. Click on Trips at the top right of the Travelocity homepage and then sign in or create an account. Or, download the Travelocity app and access your info while you're on the move. Whether you've got the family flying with you or you're a solo wanderer, all your bookings are at your fingertips.
How do I find the best deals on flights to Tripp County?
Being flexible with your travel dates is a great way to score an unbeatable deal. Travelocity makes it a snap to find your perfect fare through the "Flexible dates" feature. Search for your flight to Tripp County, then compare prices for nearby dates by hitting the Flexible dates box above. Booking in advance and avoiding vacation periods are other steps you can take. In the last seven days, the lowest price for a roundtrip flight to Tripp County was $424 on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Tripp County with Travelocity?
Browse cheap flights to Tripp County with Travelocity and start organizing your next big adventure. With 24/7 customer service during all stages of your trip and our Price Match Guarantee, we take the bother out of securing cheap family flights, hotels, experiences and more. Snap up an awesome deal today and gear up for a wonderful adventure.
How much is a flight to Tripp County on average?
In the last seven days, roundtrip flights to Tripp County were priced between $424 and $604. No matter the size of your bank account, we've got some terrific deals to help you stay within budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Tripp County?
If you're about to take a long-haul flight to Tripp County, you can generally expect food, drinks and entertainment to be included. Airlines aim to make longer flights as pleasant as possible for passengers. Quicker trips — as well as flights with low-cost airlines — may have less inclusions. If you're after cheap flights for family vacations with a budget carrier, it's possible you'll pay extra for things like food and entertainment.