Start your trip in Millennium Park, one of the most famous attractions in Chicago. See "Cloud Gate," also known as "The Bean", and take some Instagram-worthy photos. Enjoy the Crown Fountain and the interactive sculptural art of the Lurie Garden. Take a stroll towards the nearby Art Institute of Chicago, a world-renowned museum.
Start your day at Navy Pier, the most visited attraction in the Midwest. Take a ride on the Centennial Wheel and enjoy panoramic views of the skyline. Experience the Chicago Children's Museum, the Chicago Shakespeare Theater, and the Chicago Musical City. Finish off the day with a scenic dining cruise on Lake Michigan with Odyssey Chicago River.
Spend your day shopping in the iconic Magnificent Mile. Start at North Michigan Avenue and shop at famous stores like Neiman Marcus, Saks Fifth Avenue, and the American Girl Shop. Stop for lunch at the celebrity favorite, The Walnut Room at Macy's. Experience the luxurious 360 Chicago observation deck where you can enjoy breathtaking 360-degree views of the city.
End your trip with a view from the top of Willis Tower. Enjoy the spectacular views of Chicago on the Skydeck, including the famous glass ledge. Experience the high-speed elevators which will transport you to the 103rd floor in 50 seconds. End your trip with a walk around Union station, one of the oldest and historic railway stations in the nation.
If you have more time, consider visiting Grant Park or the Chicago Riverwalk. If you have less time, you can skip the shopping along the Magnificent Mile.