Prince Plays Last-Minute Intimate Late-Night Gig at Chicago's City Winery

Photo by Bria Valente

Those lucky enough to get wind of the last-minute announcement that came at 5 p.m. via City Winery's Twitter account announcing that Prince featuring New Power Generation and 3rd Eye Girl were playing the intimate West Loop venue immediately following Star Wars' creator George Lucas' star-studded wedding reception at Hyde Park's Promontory Point -- where the Artist himself was the evening's entertainment -- were frantically snapping up tickets in a frenzy that ended in just minutes, with both the $75 and $250 VIP tickets selling out this quick.

Although doors were set to open at midnight, most people -- who were lined up well around the block -- did not actually make it inside until just before Prince appeared, a smidge after 2 a.m. The famed artist known for his bling-encrusted outfits and iconic stage presence -- and who has a reputation for his late-night appearances -- took the stage wearing a pair of oversized dark sunglasses and a sizeable 'fro announcing, "Chicago, we are going to get funky tonight!"

Backed by a 22-piece band that included a dynamite 11-member brass horn section, a medley of hits including "1999," "Little Red Corvette," "Jungle Love," "U Got the Look" and a brilliant version of "The Bird" were part of the evening's setlist. "Chicago, can you dance for me?" the legendary performer asked the crowd of no more than a few hundred people who swayed and clapped while packed in closely next to one another, still in awe of the fact that it was now sometime after 3 a.m. and they were listening to Prince belt out "The Glamorous Life," even if they were forbidden from snapping just one quick picture for Instagram as the no photo/video policy was very strictly enforced.

The nearly two-hour-long show featured three encores and included a cover of Janet Jackson's "What Have You Done for Me Lately." The show finally wrapped around 4 a.m. as the crowd, still in a daze -- or as some concert attendees coined it -- a "purple haze" spilled out onto the then-desolate Randolph Street to call their Ubers, while still pinching themselves. One person on the City Winery's Facebook Page commented, "This was a gift from the Purple G-ds."