$64 Cheap Flights to Winterset, IA

Flights to Winterset at a glance

Traveling to Winterset is easy; choose between full-service and budget airlines. Compare travel times and find the best option that fits your budget and schedule, allowing you to explore the city's renowned attractions and neighborhoods. Look for cheap flights to Winterset that meet your travel needs.

• Major airport near Winterset: Des Moines International Airport (DSM)
• Flights per week: 1,900+ flights arriving at Winterset airport
• Number of airlines that fly to Winterset: around 10+ carriers

Popular airport near Winterset

Winterset is a charming city ideal for outdoor adventures, family fun, and romantic getaways. Visitors are drawn to its beautiful scenery and vibrant community. The city is conveniently accessible via a major airport, making travel planning easy for those looking to explore the area.

• Des Moines International Airport (DSM): Situated in Polk County, Iowa, approximately 24 miles from Winterset, this airport offers a range of domestic and international flights. Travelers can access over 175 domestic locations and more than 45 international spots. For those seeking additional comfort, options like first class and premium economy seating are available, depending on the specific airline and route. Major carriers operating here include American Airlines, United, and Delta.

Top routes to Winterset

• Denver (DEN) to Winterset (DSM), with one-way flight options from around $45
• Phoenix (PHX) to Winterset (DSM), with one-way fares starting at around $90
• Orlando (MCO) to Winterset (DSM), with one-way flight options from around $70
• Los Angeles (LAX) to Winterset (DSM), with one-way airfare from around $120
• Seattle (SEA) to Winterset (DSM), with one-way fares starting at around $140

Cheapest routes to Winterset

• Denver (DEN) to Winterset (DSM), with budget one-way fares from around $45
• St. Louis (STL) to Winterset (DSM), with low one-way fares from around $50
• Orlando (MCO) to Winterset (DSM), with low-cost one-way tickets from around $70
• Houston (IAH/HOU) to Winterset (DSM), with budget one-way fares from around $85
• Phoenix (PHX) to Winterset (DSM), with low one-way fares from around $90

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

Top airlines with flights to Winterset

• American Airlines: Operating flights to Des Moines International Airport (DSM), American Airlines is responsible for roughly 36% of the arrivals to Winterset. The typical one-way fare is about $270, with the potential for first-class service on select routes.
• United: With routes to Des Moines International Airport (DSM), United Airlines accounts for approximately 27% of the arrivals to Winterset. The average one-way fare is around $300, and premium service may include first class depending on the route.
• Delta: Providing flights to Des Moines International Airport (DSM), Delta makes up around 21% of arrivals in Winterset. One-way fares average about $270, with premium cabin choices that may feature both premium economy and first class based on the route.
• Southwest Airlines: Flying into Des Moines International Airport (DSM), Southwest Airlines represents about 12% of arrivals to Winterset. Travelers can expect an average one-way fare of approximately $250.
• Frontier Airlines: Operating through Des Moines International Airport (DSM), Frontier Airlines contributes roughly 3% of arrivals to Winterset. Typically a budget-friendly option, the average one-way fare is around $150.

Best time to fly to Winterset

The most popular months for travelers to fly to Winterset are January, March, and April, when peak temperatures in Winterset can reach up to 50°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 66.7°F and typically the lowest average one-way fare (around $227), roughly 12% cheaper than the yearly average. Looking for additional cheaper months to fly? October, May, and August offer average one-way fares roughly ranging from $233 to $248, 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 Winterset

Getting some of the best deals on flights to Winterset 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 Winterset 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 Winterset flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Winterset

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

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Winterset, with private rides that can be arranged in advance.
• Car rental: Renting a car in Winterset is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Winterset 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 Winterset

• Adel: Located 20 miles drive away from Winterset, Adel is a vibrant city ideal for outdoor enthusiasts and families. Visitors can enjoy a variety of activities, such as exploring the local shopping mall center and accessing scenic trails. Notable landmarks include Pedal Plaza, an urban park perfect for family outings, and the Adel Public Library, which offers a cultural touch. Whether you're seeking a leisurely day at the lake or a stroll through an urban park, Adel provides a delightful city experience for everyone.
• Cumming: Cumming is located 17 miles drive away from Winterset and offers a charming blend of family-friendly attractions and business venues. Travelers can explore shopping centers and enjoy events at the local fairground. The MidAmerican Energy Company RecPlex serves as a civic hub, while the nearby Drake University adds a modern university atmosphere. Whether you’re in town for business or leisure, Cumming’s vibrant community and diverse offerings make it a worthwhile stop.
• Patterson: Patterson is located 7 miles away from Winterset and is perfect for those looking to immerse themselves in nature. The city offers recreational areas and beautiful lakes, making it a great destination for outdoor activities. Travelers can visit the John Wayne Birthplace Museum to indulge in local culture or unwind at one of the urban parks. With its charming atmosphere, Patterson is an excellent choice for families and city explorers alike.

Tips for short-haul flights to Winterset

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 bulkiest clothing, and planning your outfits carefully. This strategy also helps you avoid the hassle of waiting at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights might not provide in-flight entertainment. Download your favorite TV shows, movies, music, or podcasts in advance, 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 advisable to arrive at least 1.5 to 2 hours prior to departure, taking into account potential traffic and security lines.
• Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Winterset

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 provide free seat selection once online check-in begins, typically 24–48 hours before your flight. Some airlines may allow 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 procedures.
• Relax at the airport—if you have some extra time, take the opportunity to explore the shops, find a coffee shop, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is usually 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 on the flight according to the local time at your arrival destination to help minimize jet lag.

Tips to find the cheapest flights to Winterset

The cheapest day to fly

Get started finding a cheap flight to Winterset 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

November is the cheapest month to fly to Winterset. 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 Winterset. 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 Winterset, 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 Winterset

The lowest price for round-trip flights to Winterset in 2026 starts from $132, while one-way tickets start from from $64. 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 Winterset. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winterset

Frontier Airlines, Delta, Southwest Airlines, American Airlines, United are just some of the airlines that can typically offer cheap tickets to Winterset. 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 Winterset and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Winterset, 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 Winterset. 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 Winterset 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 Winterset

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 Winterset.

Stopover savings

The cheapest tickets to Winterset are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Winterset. 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 Winterset 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 Winterset. Simply download the free Expedia app to your smart device and activate Winterset 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 Winterset. 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.