Friendly Skies

Founded by CEO Kenny Dichter in 2013, Wheels Up is a membership program that aims to be a total aviation solution for individuals or corporations, whatever their flight needs may be. The model is similar to that of a country club, with annual dues and a one-time initiation fee of $17,500 for families or individuals to join. Members pay for flights by the hour and have access to more than 120 aircraft like the King Air 350i and Citation Excel/XLS, which are well-suited for average private flight times of three hours or less and over 1,200 Wheels Up safety-​vetted and verified partner light, midsize, super-mid and large aircraft options. Flights can be booked with just 24 hours’ notice on the Wheels Up app or through the brand’s member-services team.

Appealing to those who want to upgrade from commercial air travel (which is more than likely most people), Wheels Up presents itself as a time-saving service, where “the vacation starts when you get on the plane,” as the company likes to put it. Cutting out the security lines and wait times of commercial aviation, Wheels Up members can travel direct to destinations like Big Sky, Montana, that are typically harder to get to. A flight from the San Francisco area to the new Montage Big Sky is estimated to take two and a half hours—if you leave in the morning, you could be on the slopes by the afternoon. The King Air 350i’s cabin accommodates up to eight passengers with room for golf bags, ski gear, and pets. (Fun fact: Thirty percent of Wheels Up charters have pets aboard.) Additional services like ground transportation can be added so the vacation vibes continue. (

Arianne Nardo

Images Courtesy of Wheels Up