Cheap Flights to Tripp County from $295 (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, Nov 12 - Sun, Nov 22
MSY
Louis Armstrong New Orleans Intl.
PIR
Pierre Regional
$334 Roundtrip, found 12 hours ago
$334
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Nov 12 from Louis Armstrong New Orleans Intl. to Pierre Regional, returning Sun, Nov 22, priced at $334 found 12 hours ago
Thu, May 13 - Mon, May 17
ICT
Wichita Dwight D. Eisenhower National
PIR
Pierre Regional
$382 Roundtrip, found 11 hours ago
$382
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 $382 found 11 hours ago
Thu, Nov 12 - Sun, Nov 22
MSY
Louis Armstrong New Orleans Intl.
PIR
Pierre Regional
$388 Roundtrip, found 12 hours ago
$388
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Nov 12 from Louis Armstrong New Orleans Intl. to Pierre Regional, returning Sun, Nov 22, priced at $388 found 12 hours ago
Thu, Nov 12 - Sun, Nov 22
MSY
Louis Armstrong New Orleans Intl.
PIR
Pierre Regional
$390 Roundtrip, found 12 hours ago
$390
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Nov 12 from Louis Armstrong New Orleans Intl. to Pierre Regional, returning Sun, Nov 22, priced at $390 found 12 hours ago
Thu, Nov 12 - Sun, Nov 22
MSY
Louis Armstrong New Orleans Intl.
PIR
Pierre Regional
$399 Roundtrip, found 12 hours ago
$399
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Nov 12 from Louis Armstrong New Orleans Intl. to Pierre Regional, returning Sun, Nov 22, priced at $399 found 12 hours ago
Thu, Nov 12 - Sun, Nov 22
MSY
Louis Armstrong New Orleans Intl.
PIR
Pierre Regional
$402 Roundtrip, found 12 hours ago
$402
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Nov 12 from Louis Armstrong New Orleans Intl. to Pierre Regional, returning Sun, Nov 22, priced at $402 found 12 hours ago
Thu, Nov 12 - Sun, Nov 22
MSY
Louis Armstrong New Orleans Intl.
PIR
Pierre Regional
$424 Roundtrip, found 12 hours ago
$424
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Nov 12 from Louis Armstrong New Orleans Intl. to Pierre Regional, returning Sun, Nov 22, priced at $424 found 12 hours ago
Thu, Nov 12 - Sun, Nov 22
MSY
Louis Armstrong New Orleans Intl.
PIR
Pierre Regional
$433 Roundtrip, found 12 hours ago
$433
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Nov 12 from Louis Armstrong New Orleans Intl. to Pierre Regional, returning Sun, Nov 22, priced at $433 found 12 hours ago
OriginDestinationTravel DatesFlights From*
DFWPierreOctober 22 to October 24$308
DENPierreSeptember 23 to October 8$345
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DENPierreSeptember 11 to September 18$445
*Prices include taxes and fees

Best Tripp County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Bel Aire Motel Chamberlain Near Missouri River I 90
2.0-star property

Bel Aire Motel Chamberlain Near Missouri River I 90

Oct 6 - Oct 9

3 night stay

Pittsburgh (PIT) to Pierre (PIR)

American Airlines • Non-stop roundtrip • Coach
Price was $721, price is now $713 per person
$713
per person
found 1 day ago
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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! (347 reviews)
"Decent hotel for the price."

Reviewed on Sep 8, 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 $308 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 November. 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 $308 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 $308 and $445. 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.