Chicago is a city with a rich history that spans from its early days as a small trading post to the bustling metropolis it is today. Home to some of the most iconic landmarks and events in the world, such as the Navy Pier and the Chicago Jazz Festival, Chicago has something for everyone. Here is your curated guide to exploring the sights and sounds of Chi-town.
Eat, See, Play
Au Cheval may call itself a diner, but there’s nothing lowbrow about it. Enjoy the fried house-made bologna sandwich and cheeseburgers, which regularly dominate the top of Chicago’s "best of" lists.
Go Michelin-Stargazing at an Award-Winning Restaurant
Chicago’s fine-dining game is strong, with 23 Michelin-starred restaurants to choose from. Reserve a table at Ever (for a decadent tasting menu), Mako (for Japanese omakase), or Elske (for seafood-heavy Scandinavian).
Chicago is home to seven professional sports teams — and in the summer, you’ll have twice the odds of winning with the Cubs and the White Sox. No matter your pick, you’ll be cheering alongside thousands of die-hard fans.
Hit the Beach…In the City
Few metropolises combine city and beach as well as Chicago, which claims more than 28 miles of shoreline. Head to North Avenue Beach for sunbathing, paddleboarding, and drinks at Castaways — all with views of downtown.
Get a Bird’s-eye View of Chi-Town’s Famous Skyline
Perched 1,000 feet above The Magnificent Mile, the John Hancock Building’s 360 Chicago observation deck takes sightseeing to the next level with a moving platform that tilts visitors nearly facedown over Michigan Avenue.
Sail the River with the Chicago Architecture Foundation
Chicago’s architecture is famous — and so are these docent-led tours of its most important landmarks. Learn about the century-old Tribune Tower to several buildings by the godfather of midcentury-modern, Mies van der Rohe.
A Mix of Innovation and Tradition
Bike, jog, or stroll The 606 Elevated Park and Trail. This path follows 2.7 miles of old rail lines combining green space, history, and art.
Warm Up with Famous Art and History
Take respite from the Windy City’s great gusts with a museum tour. Visit the Art Institute for Picasso and Matisse, the Museum of Contemporary Art for Warhol and Calder, and the Field Museum for Dinosaurs and/or pyramids.
Get to know Chicago on a new level with a private, two-hour, customized walking tour with Inside Chicago. Insights into architecture, history, art, and more fill each tour.
Glide Across the Ice in the Shadow of Cloud Gate
Millennium Park is a must no matter the season but it’s extra dazzling in the winter, when you can zip around McCormick Tribune Ice Rink for snow-laden views of the mirrored Cloud Gate and sweeping Pritzker Pavilion.