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4-Day Adventure Itinerary for Chicago in July 2023

  1. Day 1: Millennium Park
    10 minutes (1.3 miles) from Downtown Chicago

    In the morning, visit the iconic Cloud Gate sculpture, also known as “The Bean,” for a unique photo opportunity. In the afternoon, take a stroll through the Lurie Garden and the Crown Fountain, both located in Millennium Park. In the evening, enjoy a concert or show at the Jay Pritzker Pavilion.

  2. Day 2: Navy Pier
    14 minutes (3.1 miles) from Millennium Park

    Spend the morning on a thrilling speedboat ride along Lake Michigan. In the afternoon, visit the Chicago Shakespeare Theater or the Chicago Children’s Museum. In the evening, take a ride on the Ferris wheel and catch the fireworks show over the water.

  3. Day 3: The 606 Trail
    18 minutes (4.6 miles) from Navy Pier

    In the morning, rent a bike and ride the 2.7-mile-long elevated trail through the neighborhoods of Logan Square, Wicker Park, and Humboldt Park. In the afternoon, visit the National Museum of Puerto Rican Arts and Culture or the Ukrainian Institute of Modern Art. In the evening, explore the vibrant nightlife on Division Street.

  4. Day 4: Willis Tower
    20 minutes (5.3 miles) from The 606 Trail

    In the morning, visit the Skydeck on the 103rd floor of the Willis Tower for breathtaking panoramic views of the city. In the afternoon, take a guided tour of the Chicago Board of Trade or the Rookery Building. In the evening, catch a game at the United Center.

Recommendations

Other local attractions to consider include the Art Institute of Chicago, the Museum of Science and Industry, and the Field Museum. Side trips could include a day trip to the Indiana Dunes or a visit to the Frank Lloyd Wright Home and Studio in Oak Park. To maximize your fun, consider purchasing a Chicago CityPASS for discounted admission to top attractions. Don't forget to try the famous Chicago-style pizza and hot dogs. Have a great trip!

Click here to find hotels and flights for your Chicago adventure.
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