$64 Cheap Flights to Highland, WI

Popular airlines to Highland

How much is the cheapest flight to Highland?

Prices were available within the past 7 days and start at $64 for one-way flights and $118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Breeze Airways
United
American Airlines
Delta

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

August 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 2025 starts from from $118, 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 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, Breeze Airways, American Airlines, Delta, United 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.

Frequently asked questions

What month is the cheapest to fly to Highland?
October is typically the cheapest month for flights to Highland*. Look out for affordable fares during this time as you might bag a bargain. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
Which US cities have the cheapest flights to Highland?
Score cheap flights to Highland from Chicago, Detroit and Minneapolis - St. Paul. These cities typically offer the best fares to this much-loved destination. But bear in mind that holiday periods, stopovers and demand also influence rates, so remain flexible and book when prices are right.
Which US cities fly direct to Highland?
Choose from 14 US destinations with direct flights to Highland. When you book on Expedia, check the "Direct flights only" box to compare nonstop options. Fly to Highland from any of these cities:

  • Chicago
  • Detroit
  • Minneapolis - St. Paul
  • Dallas
  • Atlanta

How to find a cheap flight to Highland?
Jetting off in the low season and booking ahead of time are two great ways to get cheap flights to Highland. Or, consider flying on a Thursday, which is on average 16% cheaper than leaving on a Sunday.* Want to be the first to know when fares drop? Simply set up price tracking on the Expedia app to get real-time updates.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Highland?
Being flexible with your travel plans may help you to secure last-minute deals on cheap flights to Highland. To view all the available options, try exploring different ticket types, changing your Highland trip dates, jetting out of an alternative airport or going with another carrier.
How far in advance should I book a flight to Highland?
Lock in your flight to Highland two to four months ahead if you're visiting from an international destination. For domestic travel, the timeframe is around 28 days in advance. Lower fares and a wider variety of travel dates, schedules and seating options are just some of the awesome benefits of booking early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Highland?
You can save an average of 8% if you purchase tickets on a Sunday instead of Fridays, which tend to be the priciest day to book.* When it comes to getting a cheap flight to Highland, it's all about timing.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Highland?
You can choose from a good variety of airlines that fly to Highland. Some of your best options are:

  • Delta Air Lines - 403 flights to Highland each month, including 403 flights to Dane County Regional Airport (MSN) per month.
  • American Airlines - 394 flights to Highland each month, including 394 flights to Dane County Regional Airport (MSN) per month.
  • United Airlines - 264 flights to Highland each month, including 264 flights to Dane County Regional Airport (MSN) per month.

Can I save money by booking a Highland trip package?
Bundle your accommodations and flights and you could save hundreds of dollars. What's more, you can add extras like car rentals and tours to your Highland flight and hotel package deal. With Expedia, it's a breeze to book all your Highland travel arrangements in the same place.
Can I change or cancel my flight to Highland?
You can often cancel or change your flight to Highland within 24 hours of booking. However, be mindful that some fares are non-refundable. In those cases, you may receive credit for future travel rather than a direct refund. Remember to check the airline's terms of service in your itinerary for specific details. Use Expedia's "Changes included" or "No cancel fee" filters during your search to find cheap flights to Highland with flexible change policies. For additional information, visit our Customer Service Portal.
Flights to Highland information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Destination city name
Madison
Roundtrip price
$118

Trending flights to Highland

Prices were available within the past 7 days and start at $64 for one-way flights and $118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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*Available to One Key members.