Title: $69 Cheap Flights to Highland, WI - Expedia.com ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $69 Cheap Flights to Highland, WI [View $69 flight on Thu, Apr 16, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:DEN,to:MSN,departure:4/16/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:68.98&airProductToken=AQowCi4IxnISBDE1NjAYg2kgzGwo6MGKAzDqwooDOEVAAFgBagRQQ18xcgdSMjFRWFM5EgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Add a place to stay Direct flights only [Highland Travel Guide](https://expedia.com/Highland.dx6360555)[Hotels in Highland](https://expedia.com/Highland-Hotels.d6360555.Travel-Guide-Hotels)[Car Rentals in Highland](https://expedia.com/Car-Rentals-In-Highland.d6360555.Car-Rental-Guide)[Highland Vacation Packages](https://expedia.com/Highland.d6360555.Destination-Travel-Guides) ## Popular airlines to Highland - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Highland, Wisconsin, United States of America,departure:2/28/2026TANYT&leg2=from:Highland, Wisconsin, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Highland, Wisconsin, United States of America,departure:2/28/2026TANYT&leg2=from:Highland, Wisconsin, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Highland, Wisconsin, United States of America,departure:2/28/2026TANYT&leg2=from:Highland, Wisconsin, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Highland, Wisconsin, United States of America,departure:2/28/2026TANYT&leg2=from:Highland, Wisconsin, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Highland, Wisconsin, United States of America,departure:2/28/2026TANYT&leg2=from:Highland, Wisconsin, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Highland, Wisconsin, United States of America,departure:2/28/2026TANYT&leg2=from:Highland, Wisconsin, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Highland, Wisconsin, United States of America,departure:2/28/2026TANYT&leg2=from:Highland, Wisconsin, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Today's featured flight deals to Highland Nonstop Carry-on included Lower price than typical - Columbus (CMH)Chicago (ORD) Fri, Mar 6 Mon, Mar 9 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 4 hours ago 65% less than typical $141 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/6/2026TANYT&leg2=from:ORD,to:CMH,departure:3/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-f5e4d1dd4f7e4804b9a73a75a55749f6-2035-1-st-v5-sos-f5e4d1dd4f7e4804b9a73a75a55749f6-2031-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAaj_j1yQAQGQAQCqAQcKA0NNSBAAsgEHCgNPUkQQAQ~AQozCjEIwYIBEgQzNDQ2GII7IK4cKJLyhgMw-PKGAzhCQABYAWoFQkFTSUNyCFNWQUlaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQpuCjUIxJgBEgQxMzA2GK4cIMx8KOCZhwMwvZqHAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTVCQwo1CMSYARIEMTM1NhjMfCCCOyjhmocDMM2bhwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0E1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=504.00&displayPrice=140.59&src=dflp) - Columbus (CMH)Chicago (ORD) Fri, Mar 6 Mon, Mar 9 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 12 hours ago 60% less than typical $144 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/6/2026TANYT&leg2=from:ORD,to:CMH,departure:3/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-a8d20b4fa3d649b58e1db4f52b43b190-2405-1-st-v5-sos-a8d20b4fa3d649b58e1db4f52b43b190-2393-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAeebjlyqAQcKA0NNSBAAsgEHCgNPUkQQAQ~AQozCjEIwYIBEgQzNDQ2GII7IK4cKJLyhgMw-PKGAzhCQABYAWoFQkFTSUNyCFNWQUlaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQpwCjYIxJgBEgQyMDM5GK4cIOO0ASialIcDMOqUhwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0E1QkMKNgjEmAESBDUzMDMY47QBIII7KJ2WhwMw2paHAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTVCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE&medianPrice=469.00&displayPrice=143.60&src=dflp) - Columbus (CMH)Chicago (ORD) Fri, Mar 6 Mon, Mar 9 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 13 hours ago 60% less than typical $144 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/6/2026TANYT&leg2=from:ORD,to:CMH,departure:3/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-c48d085050b741e0afecb7f0de218434-2500-1-st-v5-sos-c48d085050b741e0afecb7f0de218434-2490-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAYWBjlyQAQGQAQGqAQcKA0NNSBAAsgEHCgNPUkQQAA~AQozCjEIwYIBEgQzNDQ2GII7IK4cKJLyhgMw-PKGAzhCQABYAWoFQkFTSUNyCFNWQUlaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQpuCjUIxJgBEgQyNzM4GK4cIOBcKKOZhwMwn5qHAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTVCQwo1CMSYARIEMTQ1ORjgXCCCOyiMm4cDMOibhwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0E1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=469.00&displayPrice=143.60&src=dflp) - Columbus (CMH)Chicago (MDW) Fri, Mar 20 Mon, Mar 23 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 3-day trip found 15 hours ago 45% less than typical $224 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/20/2026TANYT&leg2=from:MDW,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-b21f6b4bad5f47ea816cb4d5d672b72e-3167-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBv8qNXKoBBwoDQ01IEACyAQcKA0NISRAA~AQoxCi8I15wBEgQzMDQwGII7IOywASiskIgDMPeQiAM4QUAAWAFqA1dHQXIHQVhOVkgyRApgCi4I15wBEgM3MTcY7LABIPMDKKe4iAMwwrmIAzhWQABYAWoDV0dBcgdWWkFWTjJECi4I15wBEgQ0NTY2GPMDIII7KKW8iAMwrL2IAzhWQAFYAWoDV0dBcgdWWkFWTjJEEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ&medianPrice=532.00&displayPrice=223.61&src=dflp) - Columbus (CMH)Chicago (MDW) Fri, Mar 20 Mon, Mar 23 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 3-day trip found 15 hours ago 45% less than typical $224 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/20/2026TANYT&leg2=from:MDW,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-1fec86e6b89b4707b735dd1fb2c1ea3e-1364-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBvcqNXKoBBwoDQ01IEACyAQcKA0NISRAA~AQoxCi8I15wBEgQxNjIzGII7IOywASjAlYgDMIuWiAM4QUAAWAFqA1dHQXIHQVhOVkgyRApgCi4I15wBEgM3MTcY7LABIPMDKKe4iAMwwrmIAzhWQABYAWoDV0dBcgdWWkFWTjJECi4I15wBEgQ0NTY2GPMDIII7KKW8iAMwrL2IAzhWQAFYAWoDV0dBcgdWWkFWTjJEEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ&medianPrice=532.00&displayPrice=223.61&src=dflp) - Columbus (CMH)Chicago (MDW) Tue, Mar 17 Tue, Mar 24 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 6-day trip found 15 hours ago 55% less than typical $97 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/17/2026TANYT&leg2=from:ORD,to:CMH,departure:3/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-b74a3174767b4697aa1487e8cdc4f225-4133-1-st-v5-sos-b74a3174767b4697aa1487e8cdc4f225-4088-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAcDOjVyqAQcKA0NNSBAAsgEHCgNDSEkQAA~AQoxCi8I15wBEgQzNTQwGII7IOywASiu84cDMP7zhwM4VkAAWAFqA1dHQXIHVkJOVk4yRBIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE.AQozCjEIwYIBEgQzNTI2GK4cIII7KMLAiAMwlsGIAzhCQABYAWoFQkFTSUNyCE9WQUlLU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw&medianPrice=285.00&displayPrice=96.80&src=dflp) ## How much is the cheapest flight to Highland? Prices were available within the past 7 days and start at $69 for one-way flights and $123 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sun, Mar 8 - Mon, Mar 16 DEN Denver MSN Madison $123 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DEN,to:MSN,departure:3/8/2026TANYT&leg2=from:MSN,to:DEN,departure:3/16/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:122.96&airProductToken=AQowCi4IxnISBDE1NjAYg2kgzGwoyo2HAzDLjocDOEVAAFgBagRQQ18xcgdSMDdZWFM5CjAKLgjGchIENDA2MRjMbCCDaSjz6IcDMIvqhwM4RUAAWAFqBFBDXzFyB1owN1FYUzkSCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Fri, May 29 - Mon, Jun 1 LAX Los Angeles MSN Madison $204 Roundtrip found 22 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LAX,to:MSN,departure:5/29/2026TANYT&leg2=from:MSN,to:LAX,departure:6/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:203.06&airProductToken=AQouCiwIzbABEgQxNzAzGIu4ASDMbCjgpo4DMM6ojgM4QUAAWAFqAk5PcgVBTk8wMAouCiwIzbABEgQxNzAyGMxsIIu4ASiSxo4DMJPIjgM4QUAAWAFqAk5PcgVBTk8wMBIKCAEQARgBKgJNWBgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Apr 11 - Tue, Apr 14 EWR New York MSN Madison $209 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:MSN,departure:4/11/2026TANYT&leg2=from:MSN,to:EWR,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:208.80&airProductToken=AQo5CjcI1YIBEgQzNjIwGMSNASDMbCi3jIoDMN2NigM4TkAAWAFqCjFfYmFzaWNlY29yCEtGQTJBREJOCjkKNwjVggESBDM0ODIYzGwgxI0BKNSoigMw4qmKAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0ZBMkFEQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![Sun Country Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/SY.GIF) Thu, Feb 26 - Sun, Mar 1 PHX Phoenix MSN Madison $218 Roundtrip found 9 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PHX,to:MSN,departure:2/26/2026TANYT&leg2=from:MSN,to:PHX,departure:3/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:217.98&airProductToken=AQorCikI07IBEgM2ODUY77kBIMxsKMOahgMwhZyGAzhRQABYAXIHUTdEQUNBWQorCikI07IBEgM2ODYYzGwg77kBKKO-hgMwgcCGAzhRQABYAXIHUTdEQUNBWRIKCAEQARgBKgJTWRgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Apr 24 - Tue, Apr 28 EWR New York MSN Madison $229 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:MSN,departure:4/24/2026TANYT&leg2=from:MSN,to:EWR,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:228.40&airProductToken=AQppCjMIwYIBEgQxMTEzGMSNASDimgEo4piLAzDdmYsDOEJAAFgBagVCQVNJQ3IIT1ZGSFpOQlYKMgjBggESBDE1NTYY4poBIMxsKLGaiwMwu5uLAzhCQAFYAWoFQkFTSUNyCE9WRkhaTkJWCmcKMQjBggESBDQ3MzgYzGwgrhwol8iLAzDhyIsDOEJAAFgBagVCQVNJQ3IIT1ZGSFpOQlYKMgjBggESBDE5MzYYrhwgxI0BKL_JiwMwzsqLAzhCQAFYAWoFQkFTSUNyCE9WRkhaTkJWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### July is typically the cheapest month to fly From $77 - $303 per traveler. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## 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** March 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 from $123, while one-way tickets start from from $69\. 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, Sun Country Airlines, 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](https://www.expedia.com/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? ### Which US cities have the cheapest flights to Highland? ### Which US cities fly direct to Highland? > - Chicago > - Detroit > - Minneapolis - St. Paul > - Dallas > - Atlanta ### How to find a cheap flight to Highland? ### How to get a cheap last-minute flight to Highland? ### How far in advance should I book a flight to Highland? ### Which day of the week is the cheapest day to buy a plane ticket to Highland? ### Which airlines fly to Highland? > - 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? ### Can I change or cancel my flight to Highland? \*Flight schedules are subject to change. __Flights to Highland information__ | Destination airport | Dane County Regional | | ----------------------------- | -------------------- | | Destination airport IATA code | MSN | | Destination city name | Madison | | Roundtrip price | $123 | ## Trending flights to Highland Prices were available within the past 7 days and start at $69 for one-way flights and $123 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sun, Mar 8 - Mon, Mar 16 DEN Denver MSN Madison $123 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DEN,to:MSN,departure:3/8/2026TANYT&leg2=from:MSN,to:DEN,departure:3/16/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:122.96&airProductToken=AQowCi4IxnISBDE1NjAYg2kgzGwoyo2HAzDLjocDOEVAAFgBagRQQ18xcgdSMDdZWFM5CjAKLgjGchIENDA2MRjMbCCDaSjz6IcDMIvqhwM4RUAAWAFqBFBDXzFyB1owN1FYUzkSCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Spurgeon Vineyards & Winery ](https://www.expedia.com/Spurgeon-Vineyards-Winery-Hotels.0-l553248621532649577-0.Travel-Guide-Filter-Hotels) - [Hotels near Blackhawk Lake Recreation Area ](https://www.expedia.com/Blackhawk-Lake-Recreation-Area-Hotels.0-l6290068-0.Travel-Guide-Filter-Hotels) - 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