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Winner

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Winner Flights as Low as $289

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

United
Wed, Aug 5 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$289 Roundtrip, found 22 hours ago
$289
Roundtrip
found 22 hours ago
Select United flight, departing Wed, Aug 5 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 15, priced at $289 found 22 hours ago
United
Wed, Aug 5 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$318 Roundtrip, found 22 hours ago
$318
Roundtrip
found 22 hours ago
Select United flight, departing Wed, Aug 5 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 15, priced at $318 found 22 hours ago
United
Wed, Aug 19 - Sat, Aug 29
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$319 Roundtrip, found 22 hours ago
$319
Roundtrip
found 22 hours ago
Select United flight, departing Wed, Aug 19 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 29, priced at $319 found 22 hours ago
United
Wed, Aug 5 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$324 Roundtrip, found 22 hours ago
$324
Roundtrip
found 22 hours ago
Select United flight, departing Wed, Aug 5 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 15, priced at $324 found 22 hours ago
United
Wed, Aug 19 - Sat, Aug 29
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$330 Roundtrip, found 22 hours ago
$330
Roundtrip
found 22 hours ago
Select United flight, departing Wed, Aug 19 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 29, priced at $330 found 22 hours ago
United
Fri, Jan 16 - Sun, Jan 18
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$332 Roundtrip, found 23 hours ago
$332
Roundtrip
found 23 hours ago
Select United flight, departing Fri, Jan 16 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sun, Jan 18, priced at $332 found 23 hours ago
United
Fri, Jan 16 - Sun, Jan 18
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$337 Roundtrip, found 23 hours ago
$337
Roundtrip
found 23 hours ago
Select United flight, departing Fri, Jan 16 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sun, Jan 18, priced at $337 found 23 hours ago
United
Wed, Aug 5 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$353 Roundtrip, found 22 hours ago
$353
Roundtrip
found 22 hours ago
Select United flight, departing Wed, Aug 5 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 15, priced at $353 found 22 hours ago
United
Wed, Aug 12 - Sat, Aug 22
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$354 Roundtrip, found 3 days ago
$354
Roundtrip
found 3 days ago
Select United flight, departing Wed, Aug 12 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 22, priced at $354 found 3 days ago
United
Wed, Aug 5 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
PIR
Pierre Regional
$359 Roundtrip, found 22 hours ago
$359
Roundtrip
found 22 hours ago
Select United flight, departing Wed, Aug 5 from Dallas-Fort Worth Intl. to Pierre Regional, returning Sat, Aug 15, priced at $359 found 22 hours ago
United
Fri, Jan 16 - Sat, Jan 24
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$364 Roundtrip, found 23 hours ago
$364
Roundtrip
found 23 hours ago
Select United flight, departing Fri, Jan 16 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sat, Jan 24, priced at $364 found 23 hours ago
United
Sun, Jan 18 - Sat, Jan 24
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$369 Roundtrip, found 23 hours ago
$369
Roundtrip
found 23 hours ago
Select United flight, departing Sun, Jan 18 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sat, Jan 24, priced at $369 found 23 hours ago
United
Fri, Jan 16 - Sun, Jan 25
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$374 Roundtrip, found 23 hours ago
$374
Roundtrip
found 23 hours ago
Select United flight, departing Fri, Jan 16 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sun, Jan 25, priced at $374 found 23 hours ago
United
Sat, Jan 17 - Sat, Jan 24
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$374 Roundtrip, found 23 hours ago
$374
Roundtrip
found 23 hours ago
Select United flight, departing Sat, Jan 17 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sat, Jan 24, priced at $374 found 23 hours ago
United
Sun, Jan 18 - Sun, Jan 25
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$379 Roundtrip, found 23 hours ago
$379
Roundtrip
found 23 hours ago
Select United flight, departing Sun, Jan 18 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sun, Jan 25, priced at $379 found 23 hours ago
United
Sat, Jan 17 - Sun, Jan 25
DTW
Detroit Metropolitan Wayne County
PIR
Pierre Regional
$384 Roundtrip, found 23 hours ago
$384
Roundtrip
found 23 hours ago
Select United flight, departing Sat, Jan 17 from Detroit Metropolitan Wayne County to Pierre Regional, returning Sun, Jan 25, priced at $384 found 23 hours ago

Cheap Flights to Winner

Fall in love at first flight with your vacation to Winner by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winner on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winner, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winner

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winner with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the null airport.

What is the cheapest month to fly to Winner?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winner are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winner?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winner.

What airport is best to fly into Winner?

When you’re planning your trip to Winner, convenience is the name of the game. Luckily, Winner Pierre Regional Airport is nearby so you can deplane and get going on checking off everything on your Winner must-do list.

How much are flights to Winner?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winner on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $289, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winner?

The trick to saving a stack of cash on your flight to Winner? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $289 right now, why wait?

Winner Flight Information
Destination airport
Pierre Regional
Destination airport IATA code
PIR
Roundtrip price
$288

Last Minute Hotel Deals 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
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! (343 reviews)
Hot breakfast,server very kind and helpful

Reviewed on Jan 4, 2026

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Holiday 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 ...
7.6/10 Good! (320 reviews)
Staff was very nice, hotel was very clean!

Reviewed on Dec 13, 2025

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Super 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 ...
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

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Knights Inn Winner
Warrior INN

Warrior INN

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 ...
6.6/10 (8 reviews)
After staying there the last 3-4 years due to no other options, I would have given you a very poor rating due to cleanliness and major maintenance issues. But, holy cow, what an improvement this year. Much cleaner and no major issues. Thank you for the improvements

Reviewed on Nov 21, 2025

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Warrior INN
Trade Winds Motel

Trade Winds Motel

2.5 out of 5
1009 E. Hwy 20 Valentine NE
Book a stay at this business-friendly motel in Valentine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,003 reviews)
Very friendly and always clean! Our go to when in Valentine.

Reviewed on Jan 4, 2026

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Trade Winds Motel
Harmony Inn & Suites

Harmony Inn & Suites

2 out of 5
304 E Highway 20 Valentine NE
Book a stay at this business-friendly motel in Valentine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (498 reviews)
Every thing was good clean, fellow who looked after us was kind and helpful

Reviewed on Jan 4, 2026

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Harmony Inn & Suites
Comfort Inn Valentine

Comfort Inn Valentine

2.5 out of 5
101 S Main St Valentine NE
Stay at this hotel in Valentine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Trailhead ...
8.6/10 Excellent! (470 reviews)
Everything was super

Reviewed on Dec 23, 2025

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Comfort Inn Valentine
Super 8 by Wyndham Valentine NE

Super 8 by Wyndham Valentine NE

2 out of 5
223 East Highway 20 Valentine NE
Book a stay at this business-friendly motel in Valentine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (719 reviews)
Hot tub was nice and hot and jets worked amazingly well. Rooms could use updates to get into the 21st century. Had snot in the wall, holes and chipping paint on walls. Beds are hard as a brick, needed to put something in freezer but couldn’t due to it be ice covered. For the rate not what I expected ...

Reviewed on Dec 31, 2025

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Super 8 by Wyndham Valentine NE
See all 25 properties in 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.