Twenty-seven years ago, Adam Cott and a bunch of his buddies climbed into his 1974 white Opel station wagon, which he had bought from a friend of his father’s for $100, and drove from New Rochelle to Saratoga Springs, N.Y., to take in a Grateful Dead show.

They drove very slowly the whole way, in part because the car had a hole in the floor. But at least it provided a place to sleep.

Now Mr. Cott is 45, a father and entrepreneur. When he, his wife and his old crew (and their wives) head to Chicago this Fourth of July weekend to see the shows the Grateful Dead are scheduled to perform there, the accommodations will be different.

Instead of sleeping in an old car, his group will crash at the Peninsula hotel. And instead of driving in an old car, or driving at all, the group will be flying in an eight-seat private jet, at a rate of about $4,000 an hour. Their ticket packages cost almost as much, and include V.I.P. access and stadium perks.