Destination Hotels: Expert’s Picks

Isaac Bamgbose has never found a rooftop bar he didn’t like. When the 27-year-old isn’t overseeing the development of downtown’s Bottleworks complex, which will debut one of the first West Elm hotels, he soaks up the scene at stylish properties in Midwest cities that create their own perfect worlds, with every detail minded—plus a buzzy restaurant and bar. Here are four favorites:

SoHo House Chicago

West Loop, $370 per night, sohohousechicago.com

Even if you aren’t a vetted Soho House member, you can stay here or just grab a desk in the lobby, and servers from the bar and restaurant will take your order. Bamgbose is drawn to the hotel’s design and trendy neighborhood, just down the street from acclaimed restaurants like Girl & the Goat. “Think of the Scottish Rite Cathedral,” he says. “It has a sort of great-hall feeling to it. But at the same time, it’s got grit.” The buzz of people coming, going, working, and eating evolves smoothly into a happy hour and dinner scene.

Chicago Athletic Association

Chicago Athletic Association

Millennium Park, $369 per night, chicagoathletichotel.com

The entrance to this renovated historic building is unassuming, sharing an elevator foyer with a Shake Shack. “You’re not 100 percent sure where you are,” Bamgbose says. Then the lifts open onto a second-floor magnificent lobby and library, with leather Chesterfield sofas scattered around fireplaces and thick mahogany columns, like you’re in Bruce Wayne’s mansion. A bar and the expansive Game Room spread out from there, and the social scene extends to the rooftop restaurant, featuring stunning views of downtown Chicago and more architectural splendor. Room design thoroughly captures the building’s past life as a private sports club, with heritage touches like boxer-style robes and pommel-horse benches. All of those finer points add up to the immersion experience that modern travelers want. “It’s not done in a kitschy way,” Bamgbose says. “They achieved that authentic feel.”

Ironworks Hotel in Beloit, Wisconsin

Ironworks Hotel

Beloit, Wisconsin, $179 per night, ironworkshotel.com/beloit

The Ironworks brand now prominent on 86th Street (Bamgbose worked on the project) started in Beloit, a city of 36,000 where he attended college. The original Ironworks is set in a factory that produced paper-making machines. Now the industrial-cool hotel has fireplaces in every spacious room—something Bamgbose hasn’t seen anywhere else. The 54 rooms are almost always sold out—and it’s a rare hotel that you can book entirely for a wedding or event. “It’s even hard for me to get a reservation sometimes,” he says.

Hotel Covington near Cincinnati

Hotel Covington

Covington, Kentucky, $149 per night, hotelcovington.com

There’s no rooftop bar, but the restaurant and beer garden please Bamgbose just as much. “It’s green-roofed in,” he says. “You feel like you’re outside but you’re not.” The hotel—located in Kentucky’s first modern skyscraper, funded with horse-race winnings—is in a walkable part of the happening riverfront Cincinnati suburb. Evenings often end at The Walk Up, the hotel’s late-night-only food counter in a string-lit alley.