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Winona

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Winona Flights as Low as $189

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Cheap Flights to Winona

Fall in love at first flight with your vacation to Winona 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 Winona on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Winona

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winona 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 GWO airport.

What is the cheapest month to fly to Winona?

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 Winona are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winona?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Winona.

What airport is best to fly into Winona?

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

How much are flights to Winona?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winona on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $189, 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 Winona?

The trick to saving a stack of cash on your flight to Winona? 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 $189 right now, why wait?

Winona Flight Information
Destination airport
Tupelo Regional
Destination airport IATA code
TUP
Roundtrip price
$436

Last Minute Hotel Deals in Winona

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

2.5 out of 5
413 SE Frontage Road, Winona, MS
Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (648 reviews)
"Great hotel"

Reviewed on Aug 8, 2025

Holiday Inn Express and Suites Winona North by IHG
Americas Best Value Inn Winona

Americas Best Value Inn Winona

2 out of 5
301 SE Frontage Road, Winona, MS
Book a stay at this business-friendly motel in Winona. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
8/10 Very Good! (422 reviews)
"Nothing fancy but a great location and nice breakfast options."

Reviewed on Aug 6, 2025

Americas Best Value Inn Winona
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82, Winona, MS
Stay at this motel in Winona. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Winona - Montgomery County Library and Montgomery ...
5.6/10 (41 reviews)
"Met all of our needs: clean, quiet, frig, microwave, AC. Bed had unexpectedly luxurious and soft sheets."

Reviewed on Jul 23, 2025

Relax Inn & Suites
OYO Hotel Grenada West

OYO Hotel Grenada West

2 out of 5
1451 Sunset Drive, Grenada, MS
Stay at this hotel in Grenada. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Butler Hill Park and Bledsoe Park are located ...
6.4/10 (345 reviews)
"It was a very nice and clean"

Reviewed on Jul 20, 2025

OYO Hotel Grenada West
Comfort Inn & Suites Grenada

Comfort Inn & Suites Grenada

2.5 out of 5
255 Sw Frontage Rd, Grenada, MS
Book a stay at this business-friendly hotel in Grenada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (742 reviews)
"This was a great pet friendly accommodation. Rooms were quiet, clean and spacious."

Reviewed on Aug 8, 2025

Comfort Inn & Suites Grenada
Holiday Inn Express & Suites Grenada by IHG

Holiday Inn Express & Suites Grenada by IHG

2.5 out of 5
1540 Sunset Dr, Grenada, MS
Book a stay at this business-friendly hotel in Grenada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (523 reviews)
nice quick stop
"quick over night trip...very friendly staff. clean rooms. and nice breakfast in the morning."

Reviewed on Aug 6, 2025

Holiday Inn Express & Suites Grenada by IHG
Motel 6 Greenwood, MS

Motel 6 Greenwood, MS

2 out of 5
401 Highway 82 W, Greenwood, MS
Stay at this motel in Greenwood. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whittington Park and City Park are located ...
6.8/10 (106 reviews)
Clean
"The room was clean. Reasonable price. Quick check in."

Reviewed on Aug 7, 2025

Motel 6 Greenwood, MS
Baymont by Wyndham Grenada

Baymont by Wyndham Grenada

2.5 out of 5
1575 Jamison Drive, Grenada, MS
Book a stay at this business-friendly hotel in Grenada. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Butler Hill Park and Bledsoe Park ...
6/10 (641 reviews)
"Everything was nice"

Reviewed on Jul 27, 2025

Baymont by Wyndham Grenada
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.