Cheap Flights to Tripp County (2026/2027)

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Jet to one of Tripp County's top cities

Aerial View of Sturgis, South Dakota Which hosts an annual Motorcycle Rally

Winner

Flights
Winner
OriginDestinationTravel DatesFlights From*
DENPierreJuly 8 to July 20$246
DFWPierreJuly 17 to July 20$301
SLCPierreJuly 2 to July 8$435
MSPPierreAugust 6 to August 9$686
MCOPierreJuly 16 to July 16$986
ISPPierreSeptember 14 to September 20$1,423
*Prices include taxes and fees

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.
8.8/10 Excellent! (361 reviews)
"It is my home away from home. The staff are friendly and helpful. The rooms are always clean and the breakfast is top notch"

Reviewed on May 25, 2026

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! (332 reviews)
"Clean and friendly"

Reviewed on May 18, 2026

Opens in a new windowSuper 8 by Wyndham Winner SD
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
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The Ranch You Love

The Ranch You Love

Dallas SD
Stay at this vacation home in Dallas. Enjoy laundry facilities, patios, and cable/satellite TV service.
9.4/10 Exceptional! (19 reviews)
"Perfect hunting cabin."

Reviewed on Nov 22, 2025

Opens in a new windowThe Ranch You Love
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 $246 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 6 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 July. 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 $246 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 $246 and $1,423. 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.