Spend 48 hours exploring the best of Chicago, Illinois.
Start downtown and fuel up at Lou Mitchell’s, a diner from the days of Route 66, which used to roll by here. The old-school waitresses call you “doll” while delivering fluffy omelets and plate-defying flapjacks to the table.
Walk a few blocks east to the Willis Tower. Chicago’s tallest building pokes 1450 feet into the heavens, and its 103rd floor Skydeck provides a panorama over four states. Brave souls can step onto the glass-floored Ledges to be suspended (almost) in stomach-lurching mid-air.
Stay downtown and head to the Art Institute. Damn, there’s a lot of stuff hanging on the walls. It’s the second-largest art museum in the country, with masterpieces aplenty, especially impressionist and post-impressionist pieces. You’ll be eyeballing it all for at least few hours.
Make your way to the Art Institute’s 3rd floor sculpture garden, and step onto the silvery pedestrian bridge that arches over into Millennium Park. Make a beeline for the shiny “Bean” sculpture for the obligatory photo op. Splash around in Crown Fountain, where video images of locals spout gargoyle-style.
Next, hit up the nearby Chicago Architecture Foundation. Book one of the famous boat or walking tours to learn the lowdown on the city’s skyscrapers.
Dinner has to be deep-dish pizza, Chicago’s premier local specialty. Actually, Giordano’s makes “stuffed” pizza, which is a bigger, doughier version – like deep-dish on steroids. It takes 45 minutes to bake, so plan accordingly.
Finish the night at Buddy Guy’s Legends, at downtown’s southern edge. Top blues acts wail on stage nightly. The iconic guitarist himself headlines throughout January.
Have breakfast at Xoco, celeb chef Rick Bayless’ Mexican street food restaurant. Crunch into warm churros (spiraled dough fritters) and accompany with chili-spiked hot chocolate.
Next comes a choice: meander a few blocks east and browse all the big-name retailers (Nike, Uniqlo, Burberry, etc) along the Magnificent Mile (aka Michigan Avenue). Or mosey a couple miles north to the free Lincoln Park Zoo and Lincoln Park Conservatory for a morning of nature.
Decision time again. If it’s baseball season and the weather is fine, hop on the train to Wrigley Field. The ivy-walled, 1914 ballpark hosts the Cubs, a team steeped in traditions and curses (and beer). Otherwise head south to the Museum Campus and commune with dinosaurs, mummies and taxidermied creatures at the Field Museum.
The West Loop is bursting with stylish bars and restaurants. Make a dinner reservation at Little Goat, Top Chef Stephanie Izard’s comfy diner for foodies. Chow on creative burgers (say, a kimchi-bacon-and-egg-topped patty), goat sloppy joe and toffee crunch milkshakes.
Grab a cab and motor a few miles northeast to catch a show at Second City, the launching pad of jokesters from Bill Murray to Stephen Colbert and Tina Fey. The outlandish sketch revues are always high-quality laugh fests.