Cheap Flights to Winner from $299

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How Much Does it Cost To Fly To Winner?

The cheapest prices found with in the last 7 days for return flights were $304 and $299 for one-way flights to Winner for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
PIR
Pierre Regional
$349 Roundtrip, found 17 hours ago
$349
Roundtrip
found 17 hours ago
Select United flight, departing Thu, Sep 10 from Orlando Intl. to Pierre Regional, returning Mon, Sep 14, priced at $349 found 17 hours ago
OriginDestinationTravel DatesFlights From*
DFWPierreOctober 22 to October 24$304
MCOPierreSeptember 10 to September 14$349
DENPierreOctober 22 to October 25$409
MSPPierreAugust 28 to August 30$695
*Prices include taxes and fees

Winner Flight Information

Traveling to
Winner
Lowest Price
$304
Number of Airlines Serving
Airlines Serving
United
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Family Friendly Hotels in Winner

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
$117 nightly
The price is $127 total per night from Aug 29 to Aug 30
$127 total
Aug 29 - Aug 30
Total with taxes and fees
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. ...
8.8/10 Excellent! (394 reviews)
"Everything you want in hotel. Great breakfast bar. They have decaf coffee. Sleeps great. Very helpful and friendly."

Reviewed on Aug 18, 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
$79 nightly
The price is $86 total per night from Sep 4 to Sep 5
$86 total
Sep 4 - Sep 5
Total with taxes and fees
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 ...
Opens in a new windowSuper 8 by Wyndham Winner SD
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Winner?
Is Winner the first stopover on your amazing world adventure? Savvy travelers recommend booking a flight with Denver Air Connection.
Places to visit in Winner
Pack your swimmers and jump into the blue water of Winner City Pool. Need some more ideas? Visit Tripp County Veteran's Memorial, a structure that reminds us of the past.
How to get through airport security fast when traveling to Winner
If you like the idea of spending more time at the airport bars and restaurants and less time navigating your way through security on your way to Winner, just follow these suggestions:

  • Have your passport and boarding pass somewhere handy. They'll be the first things you'll be asked for by airport security staff.
  • Coins, belts and keys are to be placed in a tub for X-raying. If you pass through the body scanner with these items, you'll be turned around and requested to remove them.
  • Everyday electronics such as laptops, cameras and phones need to be put through the X-ray machine separately. Make sure they're within easy reach.
  • When you approach the security checkpoint, you'll be asked to place all creams, gels and liquids in a separate bin for inspection. Make sure they're all packed in containers smaller than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Airport security personnel will likely ask you to take off your shoes in preparation for entering the body scanner. Wear a pair that you can take off easily. There's nothing more tiresome than having to do up your laces again and again.
  • Some places have stringent quarantine laws. Consider where you're headed to and whether or not you're permitted to fly with fresh fruit and other foods.

Plane Tickets To Winner

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winner. Browse through our inventory to explore a wide range of cheap flights to Winner to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winner as you anxiously await to exit the plane and explore what Winner has to offer. Considering all the amazing local food and culture in Winner, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winner to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winner without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winner with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winner today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.