$30 Cheap Flights to Winter, WI

Flights to Winter at a glance

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

• Major airports near Winter: Duluth International Airport (DLH), Chippewa Valley Regional Airport (EAU)
• Closest (typical) airport to Winter: Chippewa Valley Regional Airport, EAU (around 70 miles)
• Flights per week: 650+ flights arriving across Winter airports
• Number of airlines that fly to Winter: around 3 carriers

Popular airports near Winter

Winter is a charming city perfect for outdoor adventures, scenic views, and romantic getaways. Travelers flock to Winter for family activities and exploration. The area is conveniently accessible through two major airports that serve the region.

• Duluth International Airport (DLH): Situated in St. Louis County, Minnesota, approximately 90 miles from Winter, this airport caters to both domestic and international flights, linking travelers to over 75 domestic cities and 2 international locations. Popular airlines, including Delta, United, and Sun Country Airlines, provide options for first-class and premium economy seating for those seeking enhanced comfort, depending on the route and airline.
• Chippewa Valley Regional Airport (EAU): Found in Chippewa County, Wisconsin, about 70 miles from Winter, this airport focuses on domestic services, connecting to more than 10 cities nationwide. United and Sun Country Airlines are among the major carriers operating here, ensuring a variety of flight options for travelers.

Top routes to Winter

• Chicago (ORD) to Winter (DLH/EAU), with one-way flights starting at around $90
• Phoenix (PHX) to Winter (DLH/EAU), with one-way flights starting at around $95
• Denver (DEN) to Winter (DLH), with one-way airfare from around $100
• Orlando (MCO) to Winter (DLH/EAU), with one-way fares starting at around $100
• Fort Myers (RSW) to Winter (DLH/EAU), with one-way flight options from around $70

Cheapest routes to Winter

• Fort Myers (RSW) to Winter (DLH/EAU), with budget one-way fares from around $70
• Chicago (ORD) to Winter (DLH/EAU), with low one-way fares from around $90
• Phoenix (PHX) to Winter (DLH/EAU), with low-cost one-way tickets from around $95
• Sarasota (SRQ) to Winter (DLH), with low-cost one-way tickets from around $100
• Denver (DEN) to Winter (DLH), with low one-way fares from around $100

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

Top airlines with flights to Winter

• Delta: Offers service to Duluth International Airport (DLH), making up approximately 47% of arrivals in Winter. The average one-way fare is around $280, with premium cabin options potentially including premium economy and first class, contingent on the specific route.
• United: Provides flights to both Duluth International Airport (DLH) and Chippewa Valley Regional Airport (EAU), constituting about 46% of arrivals to Winter. The average one-way fare stands at roughly $240, with first class available as a premium service on certain routes.
• Sun Country Airlines: Operates flights to Duluth International Airport (DLH) and Chippewa Valley Regional Airport (EAU), accounting for around 6% of Winter's arrivals. The average fare for a one-way ticket is approximately $170.

Best time to fly to Winter

The most popular months for travelers to fly to Winter are February, March, and April, when peak temperatures in Winter can reach up to 39.2°F in April. If you prefer quieter travel, consider November, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 31.3°F. For better deals, September usually offers the lowest average one-way fare around $257, roughly 8% cheaper than the yearly average. Looking for additional cheaper months to fly? October, January, and November offer average one-way fares roughly ranging from $264 to $277, 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 Winter

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

*For members. Select hotels.

Arriving in Winter

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

• Public transportation: From Duluth International Airport, Duluth Seaport, a seaport, is located about 7.2 miles away by car, while Duluth Transportation Center, a bus station, is situated approximately 7.4 miles away by car, making both easily accessible for travelers.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Winter, with private rides that can be arranged in advance.
• Car rental: Renting a car in Winter is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Winter 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 Winter

• Radisson: Nestled 11 miles away from Winter, Radisson is a charming city perfect for outdoor enthusiasts and couples seeking romance. The breathtaking scenery includes stunning lakes and trails, ideal for leisurely strolls or adventurous hikes. Key attractions include Lake Chippewa, where you can relax on the beach or explore the waters, and Ojibwa State Park, which offers a variety of outdoor activities. With a local water park and resort, Radisson is an excellent destination for a fun-filled getaway.
• Ojibwa: Located 5 miles drive away from Winter, Ojibwa is a delightful city that offers a serene escape with its picturesque landscapes. This destination is perfect for those who appreciate the great outdoors, with ample opportunities for recreation and relaxation. Explore Lake Chippewa for its romantic ambiance or venture into Ojibwa State Park for thrilling adventures amidst nature. Headflyer Island is also nearby, providing a perfect spot for a beach day or outdoor activities, making Ojibwa a great choice for nature lovers.
• Couderay: Found 14 miles away from Winter, Couderay is a lovely city that invites visitors to immerse themselves in nature's beauty. With scenic views and a tranquil atmosphere, this area is ideal for those looking for romance and adventure. Enjoy a day at Beverly Lake Wildlife Area, where outdoor activities abound, or play a round of golf at the local golf course. Couderay's proximity to Lac Courte Oreilles adds a charming touch, making it a well-rounded destination for a refreshing escape.

Tips for short-haul flights to Winter

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

• Pack light and skip checked bags—when traveling with budget airlines, it’s often more economical to stick to a carry-on. Maximize your space by bringing mini toiletries, wearing your bulkiest clothing, and planning your outfits strategically. This approach also allows you to bypass the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may not provide in-flight entertainment options. To keep yourself engaged, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. 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 traffic and security lines.
• Bring your own snacks and water—pack your favorite snacks and a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Winter

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 opens, typically 24–48 hours before your flight. Some airlines allow seat selection even earlier than this.
• Arrive at the airport in plenty of time—plan to arrive at the airport at least 3 hours before departure for international flights to allow enough time for check-in, security, and immigration.
• Relax at the airport—if you have some extra time, take the opportunity to browse 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. Aim 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 Winter

The cheapest day to fly

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

The lowest price for round-trip flights to Winter in 2026 starts from $60, while one-way tickets start from from $30. 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 Winter. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winter

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

The most affordable airports to fly into

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

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 Winter.

Stopover savings

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