The Ledge at Skydeck isn’t the only thing that brings people from around the world to The Windy City. Chicago offers an impressive mix of iconic landmarks, cultural institutions, outdoor spaces, and neighborhood experiences. Whether you want to admire Lake Michigan, visit Millennium Park’s Cloud Gate, explore the Chicago Riverwalk, shop along Michigan Avenue’s Magnificent Mile, or spend a day at one of the city’s renowned museum campuses, there is no shortage of fun things to do in Chicago. Use the sections below to explore top Chicago attractions, plan your visit, and discover experiences for every season.
Skydeck Chicago Attractions
Skydeck Chicago is one of the city’s most iconic attractions, offering unmatched views from the top of Willis Tower. From stepping onto The Ledge’s glass floor balconies to exploring immersive exhibits that showcase Chicago’s history and architecture, Skydeck delivers one of the best things to do in Chicago for first-time and returning visitors alike.
The Sights
Chicago is home to some of the most recognizable attractions in the country, from iconic architecture to scenic waterfront views. This section highlights must-see Chicago attractions that belong on every first-time and repeat visitor’s itinerary.
Tips
Planning ahead can make a big difference when exploring the best things to do in Chicago. Use these practical travel tips to navigate the city, manage your time efficiently, and maximize your overall experience.
Activities
From outdoor adventures to seasonal events and unique local experiences, there are endless fun things to do in Chicago year-round. Browse these activity ideas to build an itinerary based on your interests, travel dates, and pace.
Food
Chicago’s food scene is a destination in itself, known for iconic dishes and diverse dining neighborhoods. Explore where to eat, what to try, and how to experience the city’s most famous flavors.
Yearly and Seasonal Events
Chicago hosts a full calendar of annual festivals, holiday celebrations, and seasonal events that showcase the city at its best. From summer street festivals to winter traditions and limited-time experiences, these events add even more variety to the best things to do in Chicago throughout the year.
Make Your Time in Chicago Special With Skydeck
One of the best ways to elevate your visit is by seeing the city from 1,353 feet above street level at Skydeck Chicago. Located atop Willis Tower, Skydeck offers breathtaking views across the city and up to four states on a clear day. While Chicago is filled with unforgettable experiences, Skydeck provides a one-of-a-kind perspective that enhances any itinerary. Contact us with questions or purchase tickets online to add one of the best things to do in Chicago to your trip.
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Things to Do in Chicago FAQs
What are the best things to do in Chicago for first-time visitors?
Start with top Chicago attractions like Skydeck Chicago at Willis Tower, Millennium Park, the Chicago Riverwalk, and the Magnificent Mile. From there, add a museum stop, a neighborhood meal, and one seasonal event to round out your itinerary.
What are the most popular Chicago attractions?
Popular Chicago attractions include Skydeck Chicago and The Ledge, Millennium Park, Navy Pier, the Art Institute of Chicago, and the Museum Campus. Many visitors also prioritize river architecture tours and lakefront parks for classic city views.
What are fun things to do in Chicago with kids?
Families often enjoy interactive museums, lakefront attractions, parks, and sightseeing experiences like Skydeck. Many seasonal events and festivals also offer kid-friendly activities throughout the year.
What are fun things to do in Chicago on a rainy day?
Consider indoor Chicago attractions like museums, aquariums, immersive exhibits, shopping destinations, and indoor observation experiences. Building a flexible itinerary makes it easy to swap outdoor activities for indoor options when the weather changes.
How many days do you need to explore the best things to do in Chicago?
A weekend is enough to cover several highlights, but 3–4 days gives you more time for neighborhoods, museums, and seasonal events. Many visitors plan one major attraction per day and build around it with food, shopping, and sightseeing.
Is Skydeck Chicago worth it?
Skydeck is a top-rated Chicago attraction and a standout experience for visitors who want panoramic views of the skyline and Lake Michigan. The Ledge, a series of glass floor balconies extending from Willis Tower, is a must-do for many first-time visitors.
