Chicago is the great American city — bold, beautiful, and built with an architectural ambition that no other city in the country can match. From the deep-dish pizza to the sweeping views of Lake Michigan, a trip to the Windy City is one that stays with you long after you leave.
Top Things to Do in Chicago
Start at Millennium Park and the iconic Cloud Gate sculpture (locals call it 'The Bean') — it's the perfect introduction to Chicago's blend of public art and urban design. Walk along the Chicago Riverwalk and take an architecture boat tour on the Chicago River — this is hands-down one of the best ways to experience the city's legendary skyline.
For art, the Art Institute of Chicago is world-class and home to one of the finest collections of impressionist paintings in the world. At night, catch live blues at Buddy Guy's Legends or jazz at the Green Mill Cocktail Lounge, one of the oldest jazz clubs in America.
Chicago Neighborhoods Worth Exploring
Wicker Park and Bucktown are great for boutique shopping and creative restaurants. Pilsen on the Lower West Side has a thriving Mexican-American arts scene and excellent murals. Andersonville on the North Side is a charming, walkable neighborhood with great independent shops.
What to Pack for Chicago
Chicago weather is notoriously unpredictable — pack layers no matter what time of year you visit. A wind-resistant jacket is essential on the lakefront. The VacationGrabs Leather Backpack Briefcase Combo is ideal for a city trip where you're moving between museums and dinner reservations. For weekend trips, the VacationGrabs Large Leather Travel Duffel carries everything with room to spare.
Book Chicago Tours and Experiences
Architecture tours, deep-dish food tours, and Chicago River kayak excursions are just a few of the standout experiences available. Browse Chicago tours on Viator and plan something memorable.
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