From world-class improv at Second City to Wrigley Field’s ivy-lined outfield, Chicago is a hub of history and cultural touchstones. For visitors, it can also feel intimidatingly vast, as America’s third-largest metro area in population and land mass.
One sanity-saving option: stick close to the city’s downtown Loop. In and around this architecturally rich theater district, casual Chicago charms are tucked between storied skyscrapers and within walking distance of Navy Pier.
Our priority? Chicago-style comfort food. For pizza, skip Uno and hit Giordano’s for delectable, buttery deep-dish. Classic Italian beef is king at Portillo’s (dipped, with hot peppers). And Devil Dawgs slings the pickle-topped Chicago dog that rose to fame (and sold for a nickel) during the Great Depression. All are under two miles from Museum Campus, home to the Shedd Aquarium, Field Museum, and Soldier Field. (Da Bears!)
In summer, burn those calories on Chicago’s pedestrian Riverwalk. (Or, rent kayaks for a water-based glide.) Here, one park after another strings this popular 3.4-mile path. Near Millennium Park, find the lion-guarded Art Institute and the chrome Cloud Gate, a 66-foot sculpture resembling an interstellar kidney bean. South in Grant Park, tiered Buckingham Fountain cascades in view of are-we-sure-this-isn’t-an-ocean Lake Michigan.
For lodging, the Loop is hotel central, from the fusty, circa-1875 Palmer House to the science-themed Hotel EMC2 (complete with zoetrope machine). For more reasonable Airbnb options, try just west in Greektown or Fulton Market. And while swanky cocktail bars ring the Loop (tiki sensation Three Dots and a Dash is just across the river), venture farther for delicious hometown brews. Hop a rideshare to some of our favorites: Moody Tongue, Forbidden Root, Half Acre, and yes, Goose Island.