$56 Cheap Flights to Highland, WI

Flights to Highland at a glance

Traveling to Highland is easy—simply choose between full-service and budget airlines. Compare flight durations to find the option that best aligns with your budget, schedule, and plans to explore the city's renowned attractions and vibrant neighborhoods.

• Major airports near Highland: Dane County Regional Airport (MSN), La Crosse Municipal Airport (LSE), Dubuque Regional Airport (DBQ)
• Closest airport to Highland: Dubuque Regional Airport, DBQ (around 47 miles)
• Flights per week: 1,750+ flights arriving across Highland airports
• Number of airlines that fly to Highland: around 10+ carriers

Popular airports near Highland

Highland is a charming city perfect for outdoor enthusiasts, families, and couples seeking a romantic getaway. Visitors are drawn to its stunning scenery and adventurous activities. The city is conveniently accessed via three major airports.

• Dane County Regional Airport (MSN): Situated in Dane County, Wisconsin, approximately 53 miles from Highland, this airport offers both domestic and international flights, linking travelers to over 160 domestic cities and 25 international locales. Passengers can opt for first class or premium economy seating for enhanced comfort, depending on the airline and route. Major carriers include American Airlines, United, and Delta.
• La Crosse Municipal Airport (LSE): Found in La Crosse County, Wisconsin, about 72 miles from Highland, this airport provides domestic flights to roughly 20 cities nationwide. Travelers can upgrade to first class for a more comfortable experience, subject to the specific routes and airlines. American Airlines is the primary airline operating here.
• Dubuque Regional Airport (DBQ): Located in Dubuque County, Iowa, roughly 47 miles from Highland, this airport primarily serves domestic routes. Key Lime DBA Denver Air Connection is the main airline offering flights from this airport, catering to local travelers looking for convenient options.

Top routes to Highland

• Denver (DEN) to Highland (MSN), with one-way tickets available from around $85
• Orlando (MCO) to Highland (LSE/MSN), with one-way flights starting at around $75
• Phoenix (PHX) to Highland (LSE/MSN), with one-way airfare from around $80
• New York (JFK/LGA) to Highland (LSE/MSN), with one-way flight options from around $150
• Washington (IAD/DCA) to Highland (LSE/MSN), with one-way flight options from around $130

Cheapest routes to Highland

• Chicago (ORD) to Highland (DBQ/MSN), with low-cost one-way tickets from around $70
• Tampa (TPA) to Highland (LSE/MSN), with affordable one-way prices from around $70
• Orlando (MCO) to Highland (LSE/MSN), with low-cost one-way tickets from around $75
• Fort Myers (RSW) to Highland (MSN), with cheap one-way fares from around $75
• Phoenix (PHX) to Highland (LSE/MSN), with affordable one-way prices from around $80

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

Top airlines with flights to Highland

• American Airlines: Provides service to La Crosse Municipal Airport (LSE) and Dane County Regional Airport (MSN), representing about 42% of arrivals to Highland. The typical one-way fare hovers around $280, with first-class service available on certain routes.
• United: Operates flights to Dane County Regional Airport (MSN), accounting for roughly 29% of Highland's arrivals. The average one-way fare is approximately $280, and first class may be available depending on the specific route.
• Delta: Also flying into Dane County Regional Airport (MSN), Delta captures about 24% of arrivals to Highland. Passengers can expect an average one-way fare of around $280, with options including premium economy and first-class service based on the route.
• Frontier Airlines: Serves Dane County Regional Airport (MSN), making up about 2% of Highland's arrivals. Travelers will find the average one-way fare to be around $190, making it a budget-friendly choice.
• Breeze: Flies into Dane County Regional Airport (MSN), contributing to about 1% of arrivals in Highland. The average fare for a one-way ticket is roughly $120, offering an economical travel option.

Best time to fly to Highland

The most popular months for travelers to fly to Highland are January, March, and April, when peak temperatures in Highland can reach up to 45.5°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 63°F and typically the lowest average one-way fare (around $238), 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 $250, 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 Highland

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

*For members. Select hotels.

Arriving in Highland

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

• Public transportation: From Dane County Regional Airport, Madison Station, a train station, is located about 7.2 miles away by car, while Madison Dutch Mill Park and Ride, a bus station, is situated approximately 9.2 miles away by car, providing convenient options for onward travel.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Highland, with private rides that can be arranged in advance.
• Car rental: Renting a car in Highland is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Highland 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 Highland

• Muscoda: Located 10 miles drive away from Highland, Muscoda is a charming city that offers a delightful blend of outdoor activities and scenic views. Families will appreciate the recreational areas and hiking trails, while adventure seekers can explore the fascinating Eagle Cave. Don’t miss the A.D. German Warehouse, an architectural gem that showcases local culture, or enjoy the tranquility of the Smith Slough and Sand Prairie State Natural Area. With its rivers and lakes, Muscoda is the perfect spot for outdoor enthusiasts.
• Dodgeville: Dodgeville is located 14 miles drive away from Highland and is an excellent destination for those craving outdoor adventures and family-friendly activities. Explore the wonders of The House on the Rock, a unique tourist precinct that captivates visitors of all ages. Nature lovers can discover the breathtaking landscapes at Governor Dodge State Park or relax at Twin Valley Beach, where you can soak up the sun or enjoy a refreshing swim. Dodgeville's diverse attractions make it a great place for outdoor fun.
• Montfort: Situated 6 miles drive away from Highland, Montfort is a hidden gem for travelers seeking outdoor adventures and picturesque scenery. The Black Hawk Lake Recreation Area features a lovely beach ideal for relaxation and water activities. For those interested in history, the Fennimore Railroad Historical Society Museum offers intriguing insights into the past. Additionally, the University of Wisconsin-Platteville brings a modern touch to this charming city, making it a great spot for a day trip.

Tips for short-haul flights to Highland

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. Optimize space by using mini toiletries, wearing your heaviest clothing, and coordinating outfits effectively. This also allows you to bypass 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—even for short or domestic flights, it's advisable 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 reusable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Highland

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 provide the option for seat selection even earlier than this.
• Arrive at the airport in plenty of time—aim to arrive at least 3 hours before departure for international flights to ensure sufficient time for check-in, security screening, and immigration processes.
• Relax at the airport—if you have some extra time, take the opportunity to browse the shops, grab a coffee, 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 to synchronize your body clock by changing your watch and modifying 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 Highland

The cheapest day to fly

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

The lowest price for round-trip flights to Highland in 2026 starts from $118, while one-way tickets start from from $56. 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 Highland. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Highland

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

The most affordable airports to fly into

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

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 Highland.

Stopover savings

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