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2-Day Itinerary for Chicago in June 2023

  1. Day 1: Navy Pier
    20 minutes (5 miles) from O'Hare International Airport

    Start your day at the iconic Navy Pier. In the morning, take a ride on the Centennial Wheel for stunning views of Lake Michigan and the city skyline. In the afternoon, explore the pier's many attractions, such as the Chicago Children's Museum or the Amazing Chicago's Funhouse Maze. In the evening, catch a show at the Chicago Shakespeare Theater or enjoy a dinner cruise on one of the pier's many boats.

  2. Day 2: The Art Institute of Chicago
    10 minutes (2 miles) from Navy Pier

    Begin your day at The Art Institute of Chicago. Spend the morning exploring the museum's extensive collection of art, including works by American Gothic artist Grant Wood and Impressionist painter Claude Monet. In the afternoon, visit the nearby Millennium Park, home to the famous "Bean" sculpture. Wrap up your day with a walk along the Chicago Riverwalk, with plenty of restaurants and bars to choose from.

Recommendations

Don't forget to visit the Willis Tower Skydeck for panoramic views of the city. The Field Museum and Shedd Aquarium are also great options for families. If you have extra time, consider taking a side trip to the charming town of Oak Park, home to many Frank Lloyd Wright-designed homes.

Time and Costs Estimates

  • Navy Pier (3-4 hours, free admission)
  • The Centennial Wheel (30 minutes, $15)
  • Chicago Children's Museum (2-3 hours, $14.95)
  • Chicago Shakespeare Theater (2-3 hours, ticket prices vary)
  • Art Institute of Chicago (3-4 hours, $25)
  • Millennium Park (2-3 hours, free)
  • Chicago Riverwalk (1-2 hours, free)
  • Willis Tower Skydeck (1-2 hours, $25)
  • The Field Museum (3-4 hours, $24)
  • Shedd Aquarium (3-4 hours, $39.95)
  • Oak Park (3-4 hours, free)
  • Total Estimated Costs: $123.90+
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