Israel Temmie

Chicago has always had coffee. What it didn’t always have was time. For years, the city’s café culture moved at commuter speed: espresso shots pulled fast, laptops opened with purpose, tables turned over before the second cup cooled. Even the design of many spaces reinforced that rhythm, narrow counters, upright chairs, just enough room to pause but not settle. RECOMMENDED: Chicago was just voted one of the best cities in the U.S. for coffee lovers Lately, that logic is shifting. Across neighborhoods, a growing number of cafés are being built, or quietly reworked, around a different assumption: that people want to stay. Not indefinitely, not aimlessly, but long enough for a place to register as part of their day rather than a transaction within it. Photograph: Israel Temmie for Time OutThe Understudy At The Understudy Coffee and Books in Andersonville, the first thing that stands out is the softness. Not just in the seating, low couches, wide wooden tables, but in the way the room absorbs sound. Conversations settle into a low hum. Pages turn. Someone reads for nearly an hour without ordering a second drink, and no one interrupts them. The café doubles as a bookstore, but it doesn’t feel like a retail hybrid so much as a space calibrated for lingering. The shelves create a kind of perimeter, gently enclosing the room. It’s easy to lose track of time here, which is precisely the point. That sense of enclosure, of being held in place rather than pushed through, is becoming a

Chicago’s dining culture has long balanced polish with grit: white-tablecloth steakhouses alongside decades-old taverns, tasting menus a few blocks from shot-and-beer dives. Lately, a familiar Midwestern institution has reasserted itself in a distinctly urban way: the supper club. Not as kitsch revival, but as a format built around long dinners, strong drinks and the expectation that a night out should unfold gradually rather than end with the check. Traditional Midwestern supper clubs, particularly those in Wisconsin and northern Illinois, centered on relish trays, seafood cocktails, prime rib and brandy old fashioneds served in dim rooms where no one rushed you out the door. These meals almost always began with the relish tray, a rotating carousel of crisp radishes, celery, olives, and pickled beets, acting as a crunchy, vinegary prelude to the heavier courses to come. In Chicago, that template has evolved. Some restaurants lean into the classic ritual of carved meats and live jazz. Others blend dinner with entertainment, whiskey programs or late-night dance floors. Together, they form a version of the supper club that feels less nostalgic and more embedded in the city’s current nightlife economy. Tortoise Supper Club, in River North, is among the clearest expressions of the classic model adapted for downtown Chicago. Inside, the air is thick with the scent of roasted beef and the low hum of a jazz trio. I noticed that the room is anchored by a 'Red Room' library, where the