$93 Cheap Flights to Winona, MS

Flights to Winona at a glance

Traveling to Winona is easy; simply choose between full-service and budget airlines. Evaluate journey times and select the option that best fits your budget and schedule, all while planning to explore the city's renowned attractions and neighborhoods.

• Major airports near Winona: Evers International Airport (JAN), Golden Triangle Regional Airport (GTR)
• Closest (typical) airport to Winona: Golden Triangle Regional Airport, GTR (around 66 miles)
• Flights per week: 1,450+ flights arriving across Winona airports
• Number of airlines that fly to Winona: around 5+ carriers

Popular airports near Winona

Winona is a charming city ideal for outdoor, family, and adventure getaways. Visitors are drawn to its scenic beauty, romantic spots, and diverse activities. The city is conveniently served by two major airports, making travel easy for all who wish to explore.

• Evers International Airport (JAN): Situated in Rankin County, Mississippi, approximately 83 miles from Winona, this airport offers both domestic and international flights, linking to over 130 domestic locations and more than 15 international spots. Travelers can opt for upgrades to premium economy or first-class seating for enhanced comfort, depending on the airlines and routes. Key airlines operating here include American Airlines, Delta, and Southwest Airlines.
• Golden Triangle Regional Airport (GTR): Found in Lowndes County, Mississippi, about 66 miles from Winona, this airport provides domestic service to around 35 cities nationwide. Passengers have the option to upgrade to premium economy or first-class seating for a more comfortable journey, subject to the airlines and routes. Delta and American Airlines are among the popular carriers at this airport.

Top routes to Winona

• Chicago (ORD/MDW) to Winona (GTR/JAN), with one-way fares starting at around $120
• Las Vegas (LAS) to Winona (GTR/JAN), with one-way flights starting at around $140
• Orlando (MCO) to Winona (GTR/JAN), with one-way flight options from around $110
• New York (JFK/LGA) to Winona (GTR/JAN), with one-way flight options from around $120
• Baltimore (BWI) to Winona (GTR/JAN), with one-way tickets available from around $110

Cheapest routes to Winona

• Houston (IAH/HOU) to Winona (GTR/JAN), with low-cost one-way tickets from around $40
• Nashville (BNA) to Winona (JAN), with cheap one-way fares from around $95
• Atlanta (ATL) to Winona (GTR/JAN), with affordable one-way prices from around $95
• Washington (IAD/DCA) to Winona (GTR/JAN), with low-cost one-way tickets from around $100
• Austin (AUS) to Winona (GTR/JAN), with low-cost one-way tickets from around $100

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Winona

• Delta: Operating flights to Golden Triangle Regional Airport (GTR) and Evers International Airport (JAN), Delta represents about 37% of arrivals into Winona. The average fare for a one-way ticket is roughly $290, with premium options including premium economy and first class depending on the route.
• American Airlines: Providing service to Golden Triangle Regional Airport (GTR) and Evers International Airport (JAN), American Airlines accounts for approximately 34% of arrivals in Winona. The typical one-way fare is around $260, with first class available as a premium cabin option on certain routes.
• Southwest Airlines: Operating into Evers International Airport (JAN), Southwest Airlines is responsible for about 15% of Winona's arrivals. Travelers can expect an average one-way fare of approximately $250.
• United: Serving Evers International Airport (JAN), United contributes to around 14% of arrivals in Winona. One-way fares average about $300, offering premium service options depending on the route.
• WestJet: Flying into Evers International Airport (JAN), WestJet provides service with an average one-way fare of approximately $340.

Best time to fly to Winona

The most popular months for travelers to fly to Winona are January, March, and April, when peak temperatures in Winona can reach up to 62.6°F in April. If you prefer quieter travel, consider September, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 75.6°F. For better deals, August usually offers the lowest average one-way fare around $253, roughly 9% cheaper than the yearly average. Looking for additional cheaper months to fly? May, September, and October offer average one-way fares roughly ranging from $254 to $269, making them good options for flexible travelers.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Winona

Getting some of the best deals on flights to Winona is all about timing and flexibility. Here are some key tips to help you save:

1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Winona hotel and flight deals.
4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
5. Earn miles—you can earn airline miles when you book your Winona flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Winona

Winona welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Winona efficiently:

• Public transportation: From Evers International Airport, Jackson Station, a train station, is located about 6.8 miles away.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Winona, with private rides that can be arranged in advance.
• Car rental: Renting a car in Winona is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Winona on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Winona

• Vaiden: Vaiden is a city located 10 miles away from Winona, ideal for families and adventure seekers. Visitors can enjoy various activities at the local water park, educational facilities, and recreational areas. Key points of interest include the historic Attala County Courthouse, which reflects the area's rich culture, and Oprah Winfrey Road, a notable street for city exploration. The Winona - Montgomery County Library is also a great spot for family-friendly outings and cultural enrichment.
• Kilmichael: Kilmichael is located 9 miles away from Winona and is perfect for those seeking outdoor experiences and romantic scenery. Travelers can explore the tranquil lake and visit the local visitor center or the music museum for a taste of local culture. Highlights include the Grenada Country Club, a great spot for golf enthusiasts, and the Winona - Montgomery County Library, which offers family-friendly activities. Additionally, Winona City Hall provides a glimpse into the town's governance and community life.
• Duck Hill: Duck Hill is a village located 10 miles away from Winona that captivates outdoor lovers and adventure seekers alike. Visitors can explore its beautiful lake and recreational areas, including Jim Martin Park, which is perfect for family outings and enjoying nature. The village is also close to a national state park, making it an excellent base for outdoor activities. The Grenada Country Club offers golf, while Holmes Community College adds an educational aspect to your visit, enriching the local cultural scene.

Tips for short-haul flights to Winona

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

• Pack light and skip checked bags—with budget airlines, traveling with just a carry-on is often more economical. Maximize space by using mini toiletries, wearing your heaviest clothes, and coordinating outfits effectively. This also allows you to bypass the wait at baggage claim when you arrive.
• Bring your own entertainment—many short-haul flights do not provide in-flight entertainment. Download your favorite TV shows, movies, music, or podcasts ahead of time and consider bringing a book to keep yourself entertained. Remember to fully charge your devices before you board.
• Arrive at the airport in plenty of time—even for short or domestic flights, it’s wise to arrive at least 1.5 to 2 hours before your departure, taking into account traffic and security lines.
• Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Winona

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

• Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often allow free seat selection once online check-in opens, typically 24–48 hours before your flight. Some airlines may permit seat selection even earlier.
• Arrive at the airport in plenty of time—make sure to arrive at least 3 hours before departure for international flights to accommodate check-in, security, and immigration processes.
• Relax at the airport—if you have some extra time, take a moment to explore the shops, visit a coffee shop, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and adjusting your sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

Tips to find the cheapest flights to Winona

The cheapest day to fly

Get started finding a cheap flight to Winona on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

October is the cheapest month to fly to Winona. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Winona. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Winona, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Winona

The lowest price for round-trip flights to Winona in 2026 starts from $185, while one-way tickets start from from $93. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Winona. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winona

Southern Airways, Frontier Airlines, Southwest Airlines, United, Delta, American Airlines are just some of the airlines that can typically offer cheap tickets to Winona. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Winona and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Winona, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Winona. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Winona plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Winona

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Winona.

Stopover savings

The cheapest tickets to Winona are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Winona. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Winona for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Winona. Simply download the free Expedia app to your smart device and activate Winona flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Winona. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.