Start your morning with a thrilling Chicago River Architecture Cruise. This guided boat tour offers stunning views of the city’s world-renowned skyscrapers while delving into the history of Chicago’s architectural achievements. After the cruise, visit the Willis Tower Skydeck for panoramic views from one of the tallest buildings in the world. In the afternoon, explore the Art Institute of Chicago, home to a vast collection of artwork spanning centuries, including famous pieces like "American Gothic" and works by Monet and Picasso.

Milwaukee, Wisconsin, known for its brewing history and lakeside beauty. Begin your day with a visit to the Harley-Davidson Museum, where motorcycle enthusiasts can explore the brand’s iconic history and admire its legendary designs. Afterward, enjoy a leisurely walk or picnic along the shores of Lake Michigan, soaking in the peaceful scenery. Before heading back to Chicago, take time to explore Milwaukee’s historic Third Ward, filled with boutique shops, art galleries, and trendy cafes.

Head out for a day of nature at Indiana Dunes National Park, located along the southern tip of Lake Michigan. Spend the day hiking through diverse landscapes of sand dunes, forests, and wetlands, or relax on the park’s pristine beaches. If you’re traveling with kids, the park offers family-friendly trails and interactive nature programs. Enjoy a packed picnic lunch by the beach before driving back to Chicago in the evening, where you can dine at one of the city’s famous steakhouses.

Spend your final full day in Chicago shopping along the Magnificent Mile, home to luxury boutiques, designer stores, and department stores. After a morning of retail therapy, head to Navy Pier, where you can take in beautiful views of Lake Michigan, visit family-friendly attractions, or enjoy a ride on the Centennial Wheel. In the evening, choose from a variety of dining options at Navy Pier or along the riverfront for your final Chicago meal.

After breakfast, check out of your hotel and spend any remaining time exploring the city at your own pace. Depending on your flight schedule, you may have time for a quick visit to one of Chicago’s many museums or a walk along the lakefront. Return your rental car before heading to the airport for your departure, ending your Great Lakes adventure.