Chicago - Generated

7 May 2025 – 13 May 2025 · by matizz

Destinations

Chicago, United States

Start your journey in the Windy City, exploring cultural treasures like the Art Institute of Chicago and enjoying the architectural beauty of the skyline. Don't miss a stroll through Millennium Park, home to the iconic Cloud Gate sculpture.
Milwaukee, United States

Discover the thriving arts scene in Milwaukee, with a visit to the Milwaukee Art Museum and its stunning modern architecture. Enjoy a leisurely day exploring the historic Third Ward District, lined with charming shops and cafes.
Indianapolis, United States

Experience Indianapolis' cultural heart by visiting the Indianapolis Museum of Art and exploring the city's impressive War Memorial Plaza. Take time to enjoy its unique blend of modern and historical landmarks.
Chicago, United States

Return to Chicago to reflect on your journey and indulge in Chicago's famed deep-dish pizza. Take a river cruise to admire the city's historic architecture one last time.