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Winona

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Winona Flights as Low as $288

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

Delta
Sat, Feb 15 - Sat, Feb 15
ORD
O'Hare Intl.
JAN
Evers Intl.
$288 Roundtrip, found 4 days ago
$288
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Feb 15 from O'Hare Intl. to Evers Intl., returning Sat, Feb 15, priced at $288 found 4 days ago
American Airlines
Tue, Mar 18 - Tue, Mar 25
ORD
O'Hare Intl.
TUP
Tupelo Regional
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 18 from O'Hare Intl. to Tupelo Regional, returning Tue, Mar 25, priced at $308 found 1 day ago
Delta
Mon, Mar 3 - Mon, Mar 3
ORD
O'Hare Intl.
JAN
Evers Intl.
$314 Roundtrip, found 16 hours ago
$314
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Mar 3 from O'Hare Intl. to Evers Intl., returning Mon, Mar 3, priced at $314 found 16 hours ago
Delta
Tue, Mar 18 - Mon, Mar 24
ORD
O'Hare Intl.
JAN
Evers Intl.
$318 Roundtrip, found 6 days ago
$318
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Mar 18 from O'Hare Intl. to Evers Intl., returning Mon, Mar 24, priced at $318 found 6 days ago
American Airlines
Tue, Mar 18 - Sun, Mar 23
ORD
O'Hare Intl.
TUP
Tupelo Regional
$320 Roundtrip, found 1 day ago
$320
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 18 from O'Hare Intl. to Tupelo Regional, returning Sun, Mar 23, priced at $320 found 1 day ago
American Airlines
Tue, Mar 18 - Thu, Mar 27
ORD
O'Hare Intl.
TUP
Tupelo Regional
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 18 from O'Hare Intl. to Tupelo Regional, returning Thu, Mar 27, priced at $328 found 1 day ago
American Airlines
Tue, Mar 18 - Sat, Mar 22
ORD
O'Hare Intl.
TUP
Tupelo Regional
$335 Roundtrip, found 1 day ago
$335
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 18 from O'Hare Intl. to Tupelo Regional, returning Sat, Mar 22, priced at $335 found 1 day ago
American Airlines
Wed, Mar 19 - Wed, Mar 26
ORD
O'Hare Intl.
JAN
Evers Intl.
$337 Roundtrip, found 6 days ago
$337
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Mar 19 from O'Hare Intl. to Evers Intl., returning Wed, Mar 26, priced at $337 found 6 days ago
Delta
Tue, Mar 18 - Sat, Mar 22
ORD
O'Hare Intl.
JAN
Evers Intl.
$338 Roundtrip, found 6 days ago
$338
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Mar 18 from O'Hare Intl. to Evers Intl., returning Sat, Mar 22, priced at $338 found 6 days ago
American Airlines
Wed, Mar 19 - Wed, Mar 26
ORD
O'Hare Intl.
JAN
Evers Intl.
$340 Roundtrip, found 6 days ago
$340
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Mar 19 from O'Hare Intl. to Evers Intl., returning Wed, Mar 26, priced at $340 found 6 days ago
Delta
Tue, Jul 15 - Thu, Jul 17
MKE
General Mitchell Intl.
JAN
Evers Intl.
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 15 from General Mitchell Intl. to Evers Intl., returning Thu, Jul 17, priced at $347 found 1 day ago
United
Fri, Feb 28 - Mon, Mar 3
ORD
O'Hare Intl.
JAN
Evers Intl.
$347 Roundtrip, found 16 hours ago
$347
Roundtrip
found 16 hours ago
Select United flight, departing Fri, Feb 28 from O'Hare Intl. to Evers Intl., returning Mon, Mar 3, priced at $347 found 16 hours ago
American Airlines
Tue, Mar 18 - Sat, Mar 22
MKE
General Mitchell Intl.
TUP
Tupelo Regional
$377 Roundtrip, found 1 day ago
$377
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 18 from General Mitchell Intl. to Tupelo Regional, returning Sat, Mar 22, priced at $377 found 1 day ago
Delta
Thu, Feb 20 - Mon, Mar 3
MSY
Louis Armstrong New Orleans Intl.
GTR
Golden Triangle Regional
$407 Roundtrip, found 5 days ago
$407
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Feb 20 from Louis Armstrong New Orleans Intl. to Golden Triangle Regional, returning Mon, Mar 3, priced at $407 found 5 days ago
American Airlines
Wed, Feb 19 - Sat, Feb 22
MSY
Louis Armstrong New Orleans Intl.
TUP
Tupelo Regional
$434 Roundtrip, found 3 days ago
$434
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Feb 19 from Louis Armstrong New Orleans Intl. to Tupelo Regional, returning Sat, Feb 22, priced at $434 found 3 days ago
American Airlines
Wed, Feb 19 - Mon, Mar 3
MSY
Louis Armstrong New Orleans Intl.
JAN
Evers Intl.
$616 Roundtrip, found 5 days ago
$616
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Feb 19 from Louis Armstrong New Orleans Intl. to Evers Intl., returning Mon, Mar 3, priced at $616 found 5 days ago

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 February, 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 16 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 $288, 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 $288 right now, why wait?

Winona Flight Information
Destination airport
Evers Intl.
Destination airport IATA code
JAN
Roundtrip price
$287

Last Minute Hotel Deals in Winona

Holiday Inn Express and Suites Winona North, an IHG Hotel
Holiday Inn Express and Suites Winona North, an IHG Hotel
2.5 out of 5
413 SE Frontage Road, Winona, MS
The price is $131 per night from Feb 24 to Feb 25
$131
includes taxes & fees
Feb 24 - Feb 25
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! (596 reviews)
"Great stay and the Tesla charging was a major plus."

Reviewed on Feb 9, 2025

Holiday Inn Express and Suites Winona North, an IHG Hotel
Americas Best Value Inn Winona
Americas Best Value Inn Winona
2 out of 5
301 SE Frontage Road, Winona, MS
The price is $92 per night from Feb 12 to Feb 13
$92
includes taxes & fees
Feb 12 - Feb 13
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! (378 reviews)
"Great stay, clean safe property"

Reviewed on Jan 25, 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 Montgomery County Performing Arts Center and Winona ...
5.6/10 (39 reviews)
"Enjoyed my stay!"

Reviewed on Dec 9, 2024

Get rates
Relax Inn & Suites
Comfort Inn & Suites Grenada
Comfort Inn & Suites Grenada
2.5 out of 5
255 Sw Frontage Rd, Grenada, MS
The price is $116 per night from Mar 3 to Mar 4
$116
includes taxes & fees
Mar 3 - Mar 4
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! (671 reviews)
"Staff was friendly and helpful. Thanks for the early check in."

Reviewed on Jan 24, 2025

Comfort Inn & Suites Grenada
OYO Hotel Grenada West
OYO Hotel Grenada West
2 out of 5
1451 Sunset Drive, Grenada, MS
The price is $83 per night from Feb 16 to Feb 17
$83
includes taxes & fees
Feb 16 - Feb 17
Stay at this hotel in Grenada. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Bledsoe Park and Grenada Country Club are located ...
6.4/10 (312 reviews)
"Minor repairs are needed,but overall I think that it's a Great place"

Reviewed on Feb 6, 2025

OYO Hotel Grenada West
SureStay Plus Hotel by Best Western Greenwood
SureStay Plus Hotel by Best Western Greenwood
2.5 out of 5
635 Highway 82 W, Greenwood, MS
The price is $145 per night from Feb 14 to Feb 15
$145
includes taxes & fees
Feb 14 - Feb 15
Book a stay at this business-friendly hotel in Greenwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
8/10 Very Good! (616 reviews)
"My first time here in the property since it’s been renovated. I enjoyed my stay ( 1 night) for business. I enjoyed the dual access (from the hall and from the parking lot). I’m older and need the ability to easily transport my luggage to and from the car. The check in was flawless and I rested well ..."

Reviewed on Feb 3, 2025

SureStay Plus Hotel by Best Western Greenwood
Hampton Inn & Suites Grenada
Hampton Inn & Suites Grenada
2.5 out of 5
1545 Jameson Dr, Grenada, MS
The price is $144 per night from Feb 13 to Feb 14
$144
includes taxes & fees
Feb 13 - Feb 14
Stay at this hotel in Grenada. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (617 reviews)
"Staff members were courteous and all my questions were answered"

Reviewed on Feb 8, 2025

Hampton Inn & Suites Grenada
Holiday Inn Express & Suites Grenada, an IHG Hotel
Holiday Inn Express & Suites Grenada, an IHG Hotel
2.5 out of 5
1540 Sunset Dr, Grenada, MS
The price is $123 per night from Mar 11 to Mar 12
$123
includes taxes & fees
Mar 11 - Mar 12
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. ...
8.6/10 Excellent! (472 reviews)
"Good place, a bit pricey for where you are and what it costs."

Reviewed on Jan 26, 2025

Holiday Inn Express & Suites Grenada, an IHG Hotel
See all 51 properties in Winona
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.