Title: $71 Cheap flights from Highland, WI - Expedia.com ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $71 Cheap flights from Highland, WI [View $71 flight on Wed, May 13, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MSN,to:TPA,departure:5/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:70.65&airProductToken=AQosCioIzbABEgMxMzEYzGwg8wMo3vCMAzCK8owDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) [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 from Highland - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada - ![](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 from Highland Nonstop Carry-on included Lower price than typical - Chicago (ORD)Miami (MIA) Sun, Mar 29 Fri, Apr 3 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 4-day trip found 2 hours ago 45% less than typical $387 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MIA,departure:3/29/2026TANYT&leg2=from:MIA,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-a44d4dcdfbf044b28dd62c1c3b4010e9-694-1~8.S.1~AQoGCAEQmKwSEgcI1AQQARgBKAJYAnAAegNiZnOIAZGDrF2qAQcKA09SRBAAsgEHCgNNSUEQAA~AQozCjEIwYIBEgQyOTAxGK4cIIwCKN_6iAMwnPyIAzhCQABYAWoFQkFTSUNyCE5VQVVaT0JYCmYKMQjBggESBDE2MjIYjAIg8lwoxK2JAzCEr4kDOEJAAFgBagVCQVNJQ3IITlVBVVpPQlgKMQjBggESBDMzNTUY8lwgrhwo4a-JAzC0sIkDOEJAAVgBagVCQVNJQ3IITlVBVVpPQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=938.00&displayPrice=386.59&src=dflp) - Chicago (ORD)Miami (MIA) Sun, Mar 29 Sun, Apr 5 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 6-day trip found 4 hours ago 35% less than typical $465 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MIA,departure:3/29/2026TANYT&leg2=from:MIA,to:ORD,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-1d5dc0c7d53744199be29452513f2618-3597-1~8.S.1~AQoGCAEQjrwCEgcI1AQQARgBKAJYAnAAegNiZnOIAcrXq12qAQcKA0NISRAAsgEHCgNNSUEQAA~AQozCjEIwYIBEgQyOTAxGK4cIIwCKN_6iAMwnPyIAzhCQABYAWoFQkFTSUNyCE5VRlVaTkJYCmYKMQjBggESBDM4MTQYjAIgoQMom8OJAzC2xIkDOEJAAFgBagVCQVNJQ3IIRzBGV1pOQloKMQjBggESBDYyNjMYoQMgrhwo4sSJAzDaxYkDOEJAAVgBagVCQVNJQ3IIRzBGV1pOQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=937.00&displayPrice=464.60&src=dflp) - Chicago (ORD)Miami (MIA) Mon, Mar 23 Sat, Mar 28 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 5-day trip found 4 hours ago 40% less than typical $426 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MIA,departure:3/23/2026TANYT&leg2=from:MIA,to:ORD,departure:3/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-7899ed41baf74235bee38f54d60a92d0-82-1~8.S.1~AQoGCAEQjrwCEgcI1AQQARgBKAJYAnAAegNiZnOIAf7Zq12qAQcKA0NISRAAsgEHCgNNSUEQAA~AQozCjEIwYIBEgQxMTY0GK4cIIwCKJSxiAMw1rKIAzhCQABYAWoFQkFTSUNyCE43RlVaTkJaCmYKMQjBggESBDIyNDMYjAIgywEotOmIAzDn6ogDOEJAAFgBagVCQVNJQ3IIUzBGV1VOQlgKMQjBggESBDMwMTUYywEgrhwo3-uIAzCN7YgDOEJAAVgBagVCQVNJQ3IIUzBGV1VOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=890.00&displayPrice=425.59&src=dflp) - Chicago (ORD)Phoenix (PHX) Sun, Mar 29 Fri, Apr 3 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 4-day trip found 20 hours ago 30% less than typical $427 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:PHX,departure:3/29/2026TANYT&leg2=from:PHX,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-df6b257b88bf4e68b8c4bed122be2cb5-2151-1-st-v5-sos-df6b257b88bf4e68b8c4bed122be2cb5-2137-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAeKWqF2QASqqAQcKA0NISRAAsgEHCgNQSFgQAA~AQo0CjIIwYIBEgQzMjA1GK4cIO-5ASjP-4gDML79iAM4QkAAWAFqBUJBU0lDcghOVUFVWk5CWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQpnCjIIwYIBEgQzMjU5GO-5ASDOEiiKsYkDMJGyiQM4QkAAWAFqBUJBU0lDcghOVUFVWk5CWgoxCMGCARIENjIzOBjOEiCuHCi9sokDMMaziQM4QkABWAFqBUJBU0lDcghOVUFVWk5CWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=805.00&displayPrice=426.57&src=dflp) - Chicago (ORD)Phoenix (PHX) Sun, Mar 29 Fri, Apr 3 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 5-day trip found 1 hour ago 30% less than typical $427 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:PHX,departure:3/29/2026TANYT&leg2=from:PHX,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-68a3df636a324573a738e74c344fdec4-762-1-st-v5-sos-68a3df636a324573a738e74c344fdec4-768-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAb2trF2QASiQAQCqAQcKA0NISRAAsgEHCgNQSFgQAA~AQo0CjIIwYIBEgQzMTcyGK4cIO-5ASiV9YgDMIf3iAM4QkAAWAFqBUJBU0lDcghOVUFVWk5CWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQpnCjIIwYIBEgQxNDE0GO-5ASCDaSiHr4kDMICwiQM4QkAAWAFqBUJBU0lDcghOVUFVWk5CWgoxCMGCARIEMjgzMxiDaSCuHCirsIkDMMaxiQM4QkABWAFqBUJBU0lDcghOVUFVWk5CWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=804.00&displayPrice=426.57&src=dflp) - Chicago (ORD)Phoenix (PHX) Sun, Mar 29 Fri, Apr 3 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 5-day trip found 1 hour ago 30% less than typical $427 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:PHX,departure:3/29/2026TANYT&leg2=from:PHX,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-c64dc741954b4e7e9f6d159207843f8a-1180-1-st-v5-sos-c64dc741954b4e7e9f6d159207843f8a-1166-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZ2prF2QAQGQAR2qAQcKA09SRBAAsgEHCgNQSFgQAA~AQo0CjIIwYIBEgQzMTcyGK4cIO-5ASiV9YgDMIf3iAM4QkAAWAFqBUJBU0lDcghOVUFVWk5CWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQpnCjIIwYIBEgQzMTIwGO-5ASDDZCiKsYkDMLOyiQM4QkAAWAFqBUJBU0lDcghOVUFVWk5CWgoxCMGCARIENDkyMxjDZCCuHCiss4kDMIu0iQM4QkABWAFqBUJBU0lDcghOVUFVWk5CWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=804.00&displayPrice=426.57&src=dflp) - Chicago (ORD)Mexico City (MEX) Sat, Apr 25 Sat, May 2 ![Aeromexico](https://a.travel-assets.com/air/airlines/am_sq.svg)Aeromexico • Nonstop --- 6-day trip found 6 hours ago 60% less than typical $334 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MEX,departure:4/25/2026TANYT&leg2=from:MEX,to:ORD,departure:5/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-0d477db87fba4395a8cde94ed0658edb-989-1-st-v5-sos-0d477db87fba4395a8cde94ed0658edb-1025-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAYKYq12iAQFOqgEHCgNDSEkQALIBBwoDTUVYEAA~AQpDCkEIxJgBEgQ4MDM2GK4cIIy5ASiCqYsDMJqriwM4RUAAWAFqCU1BSU5CQVNJQ3IIVk5OTDBTQk16CQjBmgESAzY4NxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE.AQpoCjIIwYIBEgMzNzkYjLkBIKOxASiM9IsDML31iwM4QkAAWAFqBUJBU0lDcghPTk4yQVRCWgoyCMGCARIEMTEyMRijsQEgrhworfaLAzDC94sDOEJAAVgBagVCQVNJQ3IIT05OMkFUQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=1157.00&displayPrice=333.31&src=dflp) - Chicago (ORD)Mexico City (MEX) Sat, Apr 25 Mon, May 4 ![Aeromexico](https://a.travel-assets.com/air/airlines/am_sq.svg)Aeromexico • Nonstop --- 9-day trip found 4 hours ago 55% less than typical $334 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MEX,departure:4/25/2026TANYT&leg2=from:MEX,to:ORD,departure:5/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-8abe024cb0694ab78c6ddd12302cf73c-1111-1-st-v5-sos-8abe024cb0694ab78c6ddd12302cf73c-1049-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZTBq12iAQFOqgEHCgNPUkQQALIBBwoDTUVYEAA~AQpDCkEIxJgBEgQ4MDM2GK4cIIy5ASiCqYsDMJqriwM4RUAAWAFqCU1BSU5CQVNJQ3IIVk5OTDBTQk16CQjBmgESAzY4NxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE.AQpnCjIIwYIBEgQyOTk2GIy5ASCpUSigkowDMMeUjAM4QkAAWAFqBUJBU0lDcghPTk4yQVRCWgoxCMGCARIEMjgxORipUSCuHCjvlYwDMJ6XjAM4QkABWAFqBUJBU0lDcghPTk4yQVRCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=1024.00&displayPrice=333.31&src=dflp) - Chicago (ORD)Mexico City (MEX) Fri, Mar 20 Mon, Mar 23 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 19 hours ago 35% less than typical $536 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MEX,departure:3/20/2026TANYT&leg2=from:MEX,to:ORD,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-653c549b68db47c08ae4bbb1700813d6-1129-1-st-v5-sos-653c549b68db47c08ae4bbb1700813d6-990-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAcGdqF2QAQqQASqqAQcKA0NISRAAsgEHCgNNRVgQAA~AQozCjEIwYIBEgMyNDkYrhwgjLkBKNOQiAMw4JKIAzhCQABYAWoFQkFTSUNyCFFOTjNBVEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQpuCjUIxJgBEgM1ODcYjLkBIOBcKPm0iAMwvraIAzhFQABYAWoJTUFJTkJBU0lDcghUTk5GMFNCTQo1CMSYARIEMTE5ORjgXCCuHCjKuIgDMMa5iAM4RUABWAFqCU1BSU5CQVNJQ3IIVE5ORjBTQk0SCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=1070.00&displayPrice=535.51&src=dflp) ## Cheapest flights from Highland These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Wed, May 13 - Sat, May 16 MSN Madison TPA Tampa $142 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:TPA,departure:5/13/2026TANYT&leg2=from:TPA,to:MSN,departure:5/16/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:141.30&airProductToken=AQosCioIzbABEgMxMzEYzGwg8wMo3vCMAzCK8owDOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDMTMwGPMDIMxsKOOQjQMwlpKNAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Wed, Jun 3 - Sat, Jun 6 MSN Madison MCO Orlando $142 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:MCO,departure:6/3/2026TANYT&leg2=from:MCO,to:MSN,departure:6/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:141.30&airProductToken=AQosCioIzbABEgM4MDcYzGwgzHAo6eCOAzCV4o4DOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDODA2GMxwIMxsKNOBjwMwj4OPAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Wed, Jun 3 - Sat, Jun 6 MSN Madison MCO Orlando $152 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:MCO,departure:6/3/2026TANYT&leg2=from:MCO,to:MSN,departure:6/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:151.30&airProductToken=AQosCioIzbABEgM4MDcYzGwgzHAo6eCOAzCV4o4DOEFAAFgBagJFWnIFQUVaMDAKLAoqCM2wARIDODA2GMxwIMxsKNOBjwMwj4OPAzhBQABYAWoCRVpyBUFFWjAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Aug 15 - Sat, Aug 22 MSN Madison TPA Tampa $152 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:TPA,departure:8/15/2026TANYT&leg2=from:TPA,to:MSN,departure:8/22/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:151.63&airProductToken=AQosCioIzbABEgMxMzEYzGwg8wMov5KVAzDrk5UDOEJAAFgBagJOT3IFQk5PMDAKLAoqCM2wARIDMTMwGPMDIMxsKMTflQMw9-CVAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Sun Country Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/SY.GIF) Mon, Oct 26 - Mon, Nov 2 MSN Madison PHX Phoenix $158 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:PHX,departure:10/26/2026TANYT&leg2=from:PHX,to:MSN,departure:11/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:157.98&airProductToken=AQorCikI07IBEgM2ODYYzGwg77kBKK2-mwMwiMCbAzhWQABYAXIHVjJEQUNBWQorCikI07IBEgM2ODUY77kBIMxsKN6LnAMwmI2cAzhWQABYAXIHVjJEQUNBWRIKCAEQARgBKgJTWRgBIgQIARABKAIoAygEMA0) ![Sun Country Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/SY.GIF) Mon, Dec 7 - Mon, Dec 14 MSN Madison RSW Fort Myers $168 Roundtrip found 22 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:RSW,departure:12/7/2026TANYT&leg2=from:RSW,to:MSN,departure:12/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:167.98&airProductToken=AQorCikI07IBEgMxNTkYzGwg0bQBKLiXnwMw55ifAzhWQABYAXIHVjJRQUNBWQorCikI07IBEgMxNTgY0bQBIMxsKJfknwMw2OWfAzhXQABYAXIHVzREQUNBWRIKCAEQARgBKgJTWRgBIgQIARABKAIoAygEMA0) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Mon, Mar 16 - Mon, Mar 30 MSN Madison DEN Denver $182 Roundtrip found 5 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:DEN,departure:3/16/2026TANYT&leg2=from:DEN,to:MSN,departure:3/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:181.96&airProductToken=AQowCi4IxnISBDQwNjEYzGwgg2ko8-iHAzCL6ocDOEVAAFgBagRQQ18xcgdSMDdOWFM5CjAKLgjGchIEMTU2MBiDaSDMbCiKhYkDMIuGiQM4RUAAWAFqBFBDXzFyB0cwN05YUzkSCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sat, May 30 - Tue, Jun 2 MSN Madison LAX Los Angeles $200 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:LAX,departure:5/30/2026TANYT&leg2=from:LAX,to:MSN,departure:6/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:199.98&airProductToken=AQpfCi0IxnISBDQwNjEYzGwgg2ko-7OOAzCbtY4DOFpAAFgBagNFQ09yB1oxNFBYUDQKLgjGchIENDM0NRiDaSCLuAEorbaOAzDIt44DOFpAAVgBagNFQ09yB1oxNFBYUDQKXwouCMZyEgQzMTU2GIu4ASCDaSiK0Y4DMKbSjgM4WkAAWAFqA0VDT3IHWjE0UFhQNAotCMZyEgQxNTYwGINpIMxsKJ7UjgMwpNWOAzhaQAFYAWoDRUNPcgdaMTRQWFA0EgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Apr 25 - Wed, Apr 29 MSN Madison TPA Tampa $231 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:TPA,departure:4/25/2026TANYT&leg2=from:TPA,to:MSN,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:230.40&airProductToken=AQpoCjIIwYIBEgQxNTU2GMxsIOKaASiDp4sDMIqoiwM4QkAAWAFqBUJBU0lDcghPV0ZIVU5CVgoyCMGCARIEMzA1MhjimgEg8wMo5aiLAzDQqYsDOEJAAVgBagVCQVNJQ3IIT1dGSFVOQlYKZgoxCMGCARIEMzIxNRjzAyDLASir1IsDMNDViwM4QkAAWAFqBUJBU0lDcghPV0ZIVU5CVgoxCMGCARIENDU2NRjLASDMbCih14sDMMbYiwM4QkABWAFqBUJBU0lDcghPV0ZIVU5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Feb 2 - Sat, Feb 6 MSN Madison TPA Tampa $231 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:TPA,departure:2/2/2027TANYT&leg2=from:TPA,to:MSN,departure:2/6/2027TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:230.40&airProductToken=AQpyCjcI1YIBEgQzNDgyGMxsIMSNASjIlaQDMNGWpAM4TkAAWAFqCjFfYmFzaWNlY29yCEtGSzVBRkJOCjcI1YIBEgQyNzc2GMSNASDzAyj0l6QDMKSZpAM4TkAAWAFqCjFfYmFzaWNlY29yCEtGSzVBRkJOCm8KNgjVggESBDEwMTAY8wMgrhwohcakAzCvx6QDOE5AAFgBagoxX2Jhc2ljZWNvcghLRks1QUZCTgo1CNWCARIDNjMwGK4cIMxsKI7IpAMwzsikAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0ZLNUFGQk4SDAgBEAEYASoCVUEyABgBIgQIARABKAIoAygEMAs) ![](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_) ## How to Find Cheap Flights from Highland, WI #### How much is a flight from Highland? This week, flights from Highland are available between $142 – $231\. #### How to find cheap flights from Highland? Expedia makes it easy to compare cheap flights from Highland to many destinations. Check out excellent deals on domestic and international flights from Highland. Once you select an offer, use our filters and sort by “Price (Lowest)” to see some of the cheapest and suitable options. #### How can I get the best deal on flights from Highland? On Expedia, you have some of best airline ticket deals at your fingertips. Whether it’s a beach escape with your partner, a family vacation with your kids, or business trip with colleagues, these low airline ticket prices mean more savings for you. An excellent strategy for finding some of the best deals on flights from Highland is to be flexible with your dates. Within each offer, you can compare prices for similar timeframes using our “Show flexible dates” feature. Depending on your destination, direct flights from Highland may be more expensive. Airlines with strict bag policies or fees can also impact your costs. #### What is the best airline to fly from Highland? At Expedia, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Highland with: Breeze Airways, Sun Country Airlines, Frontier Airlines, American Airlines, Delta, United. #### What is the best month to fly from Highland? One of the cheapest times to fly from Highland airport(s) is May, based on the current list of flights available now. Prices on plane tickets vary considerably throughout the year due to availability and seasonal demand. #### Are there any last-minute flights from Highland? Expedia is the place to find last-minute flights from Highland, making it easy for you to compare prices on flights in the near future for different combinations of travel dates and from multiple airlines. We source some of the best deals for you and display some of the best offers available over the next 2 weeks. #### Why book your ticket with Expedia? Booking flights from Highland with Expedia is the obvious choice to get low prices, save money, and see more value from every dollar spent. We show you some of the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from, so you can find some of the cheapest flights from Highland. You can customize your journey to your timeline, route preferences, budget, rewards programs, and more. #### Can I change/cancel my flight? Some flights can be changed or canceled, but fees and refunds will depend on the unique terms of your flight agreement. Airlines have different rules and restrictions for exchanging or refunding flights. For more information, go to your itinerary or visit our [customer service portal](https://www.expedia.com/service/). We recommend choosing flights with no change fees for the most flexibility. Filter by “Flexible change policies” to see flights with no change fees. \*Data specialists from both ARC and Expedia Group analysed ARC's global flight data to distil actionable information to help people save money on travel. While it's impossible to guarantee when to find the lowest prices, after examining the variables, we were able to observe trends. Analysis based on ARC, round-trip flight data between 1 October 2017 - 30 September 2018 for Economy and Premium cabin ATPs on a global basis. ## Travel information ## Flights from Highland: Essential Travel Information | Cheapest flight from Highland | $142 (roundtrip) | | ----------------------------------- | ----------------------------------------------------------------------------------------- | | Best airlines to fly from Highland | Breeze Airways, Sun Country Airlines, Frontier Airlines, American Airlines, Delta, United | | Cheapest month to fly from Highland | May | | Highland IATA code | null | | Highland Country/State | Wisconsin | | Airline ticket deals from Highland | $142 - $231 | \*Flight schedules are subject to change. ## 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) - 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