Start the day with a caffeine fix in achingly hip Wicker Park, known for its cafés, record stores and vintage boutiques. Eighties-obsessed coffee shop The Wormhole has menus resembling video-game score screens and a life-sized replica of Back to the Future’s iconic DeLorean. The coffee is excellent, thanks to collaborations with roasters from all over the US. Afterwards, enjoy some retail therapy on N Milwaukee Ave – the main drag. Bookworms will love Myopic Books, where you’ll find thousands of second-hand books, plus readings and music recitals.
A trip downtown
There’s some fantastic architecture downtown, with highlights including the Willis Tower (America’s second-tallest building), and the Chicago Water Tower, a gothic masterpiece and one of the few structures in the area to survive 1871’s Great Fire. Downtown also has the Magnificent Mile – 13 blocks of shops and restaurants – then, for some time-out in green spaces, head to nearby Millennium Park, entered via Anish Kapoor’s gleaming bean-shaped Cloud Gate sculpture.
The first Gino’s East opened off Michigan Ave in 1966, and today it’s Chicago’s most famous pizzeria, known for its topping-laden deep dishes. Diners are invited to sign the mural-adorned walls, and there are autographed photos of famous guests including Barack Obama. We recommend the Chicago Fire, topped with fire-roasted red peppers. “We’ve always used the same recipe, which relies on cornmeal to create a golden crust,” reveals Gino’s East’s Nosheen Khan.
162 E Superior Street, 60611; +1 312-266-3337
This architectural gem is one of America’s largest botanical conservatories, with two acres of indoor gardens and 10 acres outside. Must-sees include the 65-foot-high Palm House, the Aroid House, for its art-like arrangements of lily pads, and the Fern Room, where displays of ancient cycads are designed to resemble the swampy landscape of prehistoric Illinois.
300 N Central Park Ave, 60624; +1 312-746-5100
Got a head for heights? Sunset is the perfect time to visit the observation deck on the John Hancock Building’s 94th floor. You’ll enjoy 360-degree views over the windy city, and if you’re feeling brave, there’s Tilt – an enclosed, moving platform that tilts you over Michigan Avenue.
875 N Michigan Ave, 60611; +1 888-875-8439
Dinner and a show
Two Lights Seafood & Oyster, in Chicago’s old town, is a restaurant with a wonderfully retro vibe – think pastel-pink walls and lots of neon. There’s a rotating selection of oysters, and other highlights include a delicious steak tartare with oyster aioli. The restaurant is a popular stop-off for those heading to nearby Second City comedy club, where Steve Carell and John Candy cut their teeth. The venue comprises several theatres, and the improv performances are legendary – you can even sign up for workshops.
227 W North Ave; +1 312-929-3091
Enjoy a nightcap at Chicago’s famous House of Blues live music venue, where a box of Mississippi mud is welded underneath the stage to help artists channel the spirit of the South. Performances often start after midnight, so it’s a great place for a final toast to Chicago. If you’re craving something sweet, the ice-cream-topped skillet cookie will do the job.
329 N Dearborn, 60654; +1 312-923-2000