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Boston to Chicago Family-Friendly Itinerary

Thursday, August 31: Boston Arrival

Welcome to Boston! Start your family-friendly adventure by exploring the historic Freedom Trail in the morning. This 2.5-mile long trail will take you to 16 significant sites, including the Massachusetts State House and Paul Revere's House. In the afternoon, head to the New England Aquarium, where you can marvel at a wide variety of marine life. Wrap up the day with a relaxing evening stroll in the beautiful Boston Common.

  • Freedom Trail: Free, 3-4 hours
  • New England Aquarium: Adults $32.99, Children $23.99, 2-3 hours
  • Boston Common: Free, 1-2 hours
Friday, September 1: Niagara Falls Excursion

Today, take a day trip to experience the awe-inspiring Niagara Falls. Start your morning with a scenic drive to Niagara Falls State Park. Spend the morning exploring the park and getting up close to the magnificent falls. Afterward, enjoy a thrilling Maid of the Mist boat tour to feel the mist on your face. In the evening, visit Clifton Hill and enjoy the vibrant atmosphere, with its arcades, mini-golf, and delicious dining options.

  • Niagara Falls State Park: $25 per vehicle, 4-5 hours
  • Maid of the Mist: Adults $22.25, Children $13, 1-2 hours
  • Clifton Hill: Varies, 2-3 hours
Saturday, September 2: Chicago Exploration

Arrive in the bustling city of Chicago and start your day with a visit to the iconic Navy Pier. Enjoy a morning ride on the Ferris wheel for stunning views of the city and Lake Michigan. In the afternoon, explore the interactive exhibits at the Museum of Science and Industry. As evening approaches, head to Millennium Park and be captivated by the famous Cloud Gate sculpture, also known as "The Bean."

  • Navy Pier: Free admission, Ferris wheel ride $18, 2-3 hours
  • Museum of Science and Industry: Adults $21.95, Children $12.95, 3-4 hours
  • Millennium Park: Free, 1-2 hours
Sunday, September 3: Family Fun Day

For your last day, immerse yourself in family-friendly fun at the Chicago Children's Museum. Spend the morning exploring the hands-on exhibits and engaging activities. In the afternoon, visit the Shedd Aquarium, where you can marvel at aquatic creatures from around the world. Wrap up your trip with a relaxing evening stroll along the beautiful Lakefront Trail.

  • Chicago Children's Museum: Adults $19, Children $14, 2-3 hours
  • Shedd Aquarium: Adults $39.95, Children $29.95, 3-4 hours
  • Lakefront Trail: Free, 1-2 hours

Hidden Gems and Local Favorites

When in Chicago, make sure to explore Lincoln Park Zoo, a free zoo with a wide range of animals that will delight both kids and adults. Another local favorite is the Chicago Architecture Foundation Center River Cruise, where you can enjoy a leisurely boat tour along the Chicago River, learning about the city's stunning architectural landmarks. These hidden gems provide unique experiences and are perfect for families seeking a memorable adventure.

Check hotel and flight prices for your Boston to Chicago trip here!

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