Summer 2025 in the Windy City is full of exciting surprises, offering something for everyone. From iconic landmarks to scenic waterfronts, Chicago is a vibrant destination for visitors and locals alike. Whether you’re discovering the city for the first time or looking for new adventures, this guide will help you make the most of your summer in Chicago.
1. Start with the Best View: Skydeck Chicago
For a breathtaking introduction to things to do in Chicago this summer, begin at Skydeck Chicago, located on the 103rd floor of the historic Willis Tower (formerly the Sears Tower). At 1,353 feet above the city, Skydeck offers the tallest observation experience in the Western Hemisphere.
Step onto The Ledge, a thrilling glass-floor balcony extending over 4.3 feet from the building’s edge, giving you an unobstructed view of Chicago’s stunning skyline. From here, you’ll take in a panoramic vista that stretches across Illinois, Indiana, Michigan, and Wisconsin. There’s no better place to start your summer activities in Chicago!
Skydeck Chicago is a three-in-one attraction. In addition to enjoying the breathtaking views and The Ledge, don’t miss the Chicago Museum experience. Take an immersive museum tour that showcases the rich history of Willis Tower and Chicago’s architectural legacy. Explore engaging exhibits before heading up to witness the city from above.
2. Take a Stroll on the Chicago Riverwalk
After taking in the views from Skydeck, head to the Chicago Riverwalk, a 1.25-mile scenic pathway along the Chicago River. This picturesque stretch offers unique perspectives of the city’s incredible architecture and reflects its industrial and economic history.
3. Visit the McCormick Bridgehouse & Chicago River Museum
Located along the Riverwalk, stop at the McCormick Bridgehouse and Chicago River Museum to see how Chicago’s waterways helped shape the city. This fascinating cultural center gives visitors a deeper insight into Chicago’s rich history and development. This attraction is a must for history and engineering enthusiasts.
4. Experience Chicago’s Shoreline
From Navy Pier to Grant Park, past the impressive Field Museum, and onto Northerly Island Park, the shoreline of Lake Michigan is one place you could explore for days on end.
Home to historic sites and world-famous landmarks, this shoreline area of Chicagoland has something for everyone. Whether you want to visit the Art Institute of Chicago or explore the cosmos at the Adler Planetarium, your curiosity and cultural appetites are well tended.
5. Visit the Lincoln Park Zoo
Lincoln Park Zoo is one of the last free-admission zoos in America. It offers 35 acres of animal kingdom wonder, perhaps best known for its Great Ape House, which houses chimpanzees and gorillas. The Zoo also features penguins at Pritzker Penguin Cove and offers a wide variety of animal experiences.
6. End Your Day at Skydeck
Be sure to wrap up your list of events in Chicago at Skydeck, where it all began. Take in the city’s dazzling night skyline because there’s no better way to appreciate the beauty and energy of Chicago than from above.
Plan your visit to Skydeck and experience the best views of the city from the top of Willis Tower!