Chicago Athletic Association

Chicago’s architectural story began before modernism — this Venetian Gothic landmark, previously a private club for the city’s (male) movers and shakers, dates back to the final decade of the 19th century. But now, after a renovation by architects Hartshorne Plunkard and an interior redesign by hospitality wizards Roman and Williams, the Chicago Athletic Association is a thoroughly up-to-date boutique hotel, in that retro-modern, luxury-boutique sort of way.

These sorts of things live and die by their raw materials, but rest assured that this one is a true gem. It’s not just any old building, but a beautiful old building, and there are clearly plenty of tricks left up Roman and Williams’s collective sleeve. It doesn’t hurt that you’re looking straight out over Millennium Park, but there’s plenty worth looking at indoors as well — much of what you see is custom-designed, what’s not is expertly sourced, and a little originality in hotel design goes a long way these days.

So does a little bit of extravagance in the food and drink departments. Cindy’s is the rooftop terrace restaurant, and the Cherry Circle Room brings the Athletic Association’s long-serving dining room back to life, with inspiration from a century of menus. The Game Room and the Milk Room are (fraternal) twin speakeasy-style cocktail bars, the former featuring plenty of games and the latter largely substituting whiskey for milk. And an outpost of the New York–based (now global) Shake Shack, needless to say, is a natural fit for the Chicago Athletic Association — or for just about any hotel, if we’re being completely honest.