$46 Cheap Flights to Winston, OR

Flights to Winston at a glance

Traveling to Winston is easy; you can choose between full-service and budget airlines. Compare travel times and select the flight that best fits your budget and schedule, allowing you to explore the city's renowned attractions and neighborhoods.

• Major airports near Winston: Eugene Airport (EUG), Rogue Valley International Airport (MFR)
• Closest (typical) airport to Winston: Rogue Valley International Airport, MFR (around 59 miles)
• Flights per week: 2,650+ flights arriving across Winston airports
• Number of airlines that fly to Winston: around 10+ carriers

Popular airports near Winston

Winston is a charming city perfect for outdoor adventures, scenic views, and family getaways. Visitors are drawn to its romantic atmosphere and beautiful landscapes. The city is conveniently accessible through two major airports, making travel hassle-free for all.

• Eugene Airport (EUG): Situated in Lane County, Oregon, approximately 70 miles from Winston, this airport facilitates both domestic and international travel, linking to around 155 domestic cities and over 20 international destinations. Passengers have the option to upgrade to business class, first class, or premium economy class seating for enhanced comfort, depending on the selected routes and airlines. Major carriers at this airport include United, Alaska Airlines, and Southwest Airlines.
• Rogue Valley International Airport (MFR): Found in Jackson County, Oregon, about 59 miles from Winston, this airport handles both domestic and international flights, providing connections to more than 120 domestic cities and over 20 international locales. Travelers can opt for upgrades to first class, premium economy class, or business class seating for a more comfortable journey, depending on the routes and airlines. Key airlines operating here include United, Alaska Airlines, and Delta.

Top routes to Winston

• Los Angeles (LAX) to Winston (EUG/MFR), with one-way flight options from around $80
• Phoenix (PHX) to Winston (EUG/MFR), with one-way tickets available from around $70
• San Diego (SAN) to Winston (EUG/MFR), with one-way flights starting at around $80
• Las Vegas (LAS) to Winston (EUG/MFR), with one-way tickets available from around $70
• San Francisco (SFO) to Winston (EUG/MFR), with one-way tickets available from around $85

Cheapest routes to Winston

• Seattle (SEA) to Winston (EUG/MFR), with affordable one-way prices from around $50
• Portland (PWM/PDX) to Winston (EUG/MFR), with cheap one-way fares from around $60
• Burbank (BUR) to Winston (EUG/MFR), with affordable one-way prices from around $65
• Long Beach (LGB) to Winston (EUG), with low one-way fares from around $70
• Phoenix (PHX) to Winston (EUG/MFR), with budget one-way fares from around $70

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

Top airlines with flights to Winston

• United: Operating flights to Eugene Airport (EUG) and Rogue Valley International Airport (MFR), United makes up about 31% of arrivals in Winston. Passengers can expect an average one-way fare of around $280. Premium service may feature first class based on the route.
• Alaska Airlines: Providing service to Eugene Airport (EUG) and Rogue Valley International Airport (MFR), Alaska Airlines accounts for roughly 27% of Winston's arrivals. The average one-way fare is about $260, with premium cabin options potentially including business class and first class depending on the route.
• Delta: With flights to Eugene Airport (EUG) and Rogue Valley International Airport (MFR), Delta represents approximately 18% of arrivals to Winston. Expect average one-way fares of around $270, with premium cabin choices possibly including premium economy and first class based on the route.
• American Airlines: Serving Eugene Airport (EUG) and Rogue Valley International Airport (MFR), American Airlines makes up approximately 13% of arrivals to Winston. The typical one-way fare is around $290, and premium service may feature first class depending on the route.
• Southwest Airlines: Flying into Eugene Airport (EUG), Southwest Airlines contributes about 9% of Winston's arrivals. Travelers can anticipate an average one-way fare of roughly $250.

Best time to fly to Winston

The most popular months for travelers to fly to Winston are January, March, and April, when peak temperatures in Winston can reach up to 46.6°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 60.1°F and typically the lowest average one-way fare (around $231), roughly 9% cheaper than the yearly average. Looking for additional cheaper months to fly? August, October, and May offer average one-way fares of around $241, 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 Winston

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

*For members. Select hotels.

Arriving in Winston

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

• Public transportation: From Eugene Airport, Eugene Station, a train station, is located about 7.4 miles from the airport.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Winston, with private rides that can be arranged in advance.
• Car rental: Renting a car in Winston is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Winston 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 in and around Winston

• Roseburg: Located 7 miles drive away from Winston, Roseburg is a charming city known for its stunning outdoor scenery and adventure opportunities. Travelers can enjoy a variety of activities in the area, including visits to the Douglas County Museum of History and Natural History for a cultural experience, or a relaxing day at Stewart Park, perfect for families. For nature enthusiasts, the nearby Winchester Dam and national parks provide breathtaking views and recreational activities, making Roseburg an excellent destination for outdoor lovers.
• Myrtle Creek: Myrtle Creek is located 9 miles drive away from Winston and offers a delightful blend of outdoor adventure and romantic scenery. Visitors can explore the serene surroundings at Millsite Park or take a moment to reflect at Myrtle Creek Memorial Park. The modern Myrtle Creek City Hall stands as a testament to the city’s community spirit. With its proximity to beautiful national parks and lakes, Myrtle Creek is a great spot for couples seeking a quiet retreat or families looking to enjoy nature.
• Dillard: Dillard is located in the area of Winston and is a quaint village that beckons travelers with its outdoor charm and scenic beauty. The South Umpqua River is a highlight for those who enjoy water activities and picturesque views. History buffs can delve into the past at the Douglas County Museum of History and Natural History, while families can unwind at Stewart Park. Dillard’s close-knit community and natural attractions make it a perfect stop for anyone looking to explore the region’s outdoor adventures.

Tips for short-haul flights to Winston

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

• Pack light and skip checked bags—when flying with budget airlines, it's often more economical to travel with just a carry-on. Maximize space by packing mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This approach also helps you avoid the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself engaged. Remember to fully charge your devices before you board.
• Arrive at the airport in plenty of time—for both short and domestic flights, it's advisable to arrive at least 1.5 to 2 hours prior to 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 Winston

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

• Select your seat in advance—for longer flights, choosing your seat is crucial for comfort. Full-service airlines typically allow complimentary seat selection once online check-in opens, which is usually 24–48 hours prior to your flight. Some airlines may permit seat selection even earlier.
• Arrive at the airport in plenty of time—aim to reach the airport at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
• Relax at the airport—if you find yourself with extra time, take the opportunity to explore the shops, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Most airports offer free and accessible Wi-Fi.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and sleep routine to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Tips to find the cheapest flights to Winston

The cheapest day to fly

Get started finding a cheap flight to Winston 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 Winston. 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 Winston. 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 Winston, 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 Winston

The lowest price for round-trip flights to Winston in 2026 starts from $92, while one-way tickets start from from $46. 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 Winston. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winston

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

The most affordable airports to fly into

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

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 Winston.

Stopover savings

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