I went to Chicago once as a child and was excited to go back as an adult. This time, I had a really nice weekend getaway and got to experience the city in a whole new way. I highlighted a few of the best places to visit, from iconic landmarks to hidden gems, and even discovered some incredible restaurants in Chicago that made the trip even more memorable. For my stay, I chose an Airbnb right across from Millennium Park, which made it easy to walk to many attractions and explore the downtown area. In this travel guide, I’ll share my top recommendations for things to do in Chicago, the best restaurants in Chicago to try during your visit, and tips on where to stay in Chicago so you can plan the perfect Windy City trip.
Things to do in Chicago
Skydeck at Willis Tower
If you’re not afraid of heights, then this would be a perfect attraction for you to visit. The Willis Tower Skydeck is one of the top attractions in Chicago, giving visitors a chance to see the city from more than 1,300 feet above the ground. The highlight is The Ledge, a glass balcony that extends out from the building, offering breathtaking views and the ultimate photo opportunity. If you’re putting together your list of must visit things to do in Chicago, the Skydeck is a bucket list experience that combines thrill and stunning scenery all in one stop.
The Bean
One of the most iconic landmarks in the city, The Bean at Millennium Park, officially named Cloud Gate, is a must-see when exploring Chicago. Its shiny, mirrored surface reflects the city skyline and makes it one of the most photographed spots in town. Whether you’re walking through downtown, planning fun things to do in Chicago, or staying nearby at one of the top hotels in Chicago, visiting The Bean is an essential stop for first time visitors and locals alike.
Navy Pier
No trip to the city is complete without a visit to Navy Pier, one of the most popular attractions in Chicago. Stretching out into Lake Michigan, the pier is home to restaurants, shops, boat cruises, and the famous Centennial Wheel, offering stunning views of the skyline. It’s a perfect addition to your list of things to do in Chicago, whether you’re planning a family outing, a romantic date, or just looking for a fun way to enjoy the lakefront.
The Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and most renowned art museums in the United States, making it a must on any list of things to do in Chicago. Located just steps from Millennium Park, the museum houses an impressive collection that spans centuries and includes iconic works like Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte. Whether you’re an art lover or simply looking for a cultural highlight during your trip, the Art Institute offers an inspiring experience in the heart of the city.
More recommendations:
- Wrigley Field
Restaurants in Chicago
The Kitchen
The Kitchen is a modern American restaurant located along the Chicago Riverwalk, offering both stunning views and a menu focused on fresh, seasonal ingredients. Known for its welcoming atmosphere and commitment to community, it’s a great place to enjoy everything from weekend brunch to a relaxed dinner with friends. If you’re exploring restaurants in Chicago and want a spot that combines style, flavor, and a prime location, The Kitchen is a must-try during your visit.
Bubba Gump Shrimp
Bubba Gump Shrimp Co. is a lively, family-friendly restaurant located on Navy Pier, making it a fun stop during your Chicago adventures. Inspired by the movie Forrest Gump, the restaurant serves seafood favorites like shrimp dishes, fish and chips, and classic Southern comfort food. With its casual vibe and prime location, it’s one of the most popular restaurants in Chicago for visitors who want good food with a playful, themed dining experience.
Garrett’s Popcorn
Garrett Popcorn Shops are a Chicago classic, famous for their irresistible gourmet popcorn made fresh in small batches. The signature Garrett Mix, a blend of sweet caramel crisp and savory cheese corn, has become a must-try treat for both locals and visitors. With several locations throughout the city, Garrett Popcorn is an easy and delicious stop to add to your list of things to do in Chicago, whether you’re grabbing a snack while exploring or taking a tin home as a souvenir.
Chicago is a city that blends history, culture, food, and architecture in a way that makes every trip unforgettable. From world famous attractions like Millennium Park and Navy Pier to local gems tucked away in different neighborhoods, there are endless things to do in Chicago no matter the season. Pair your sightseeing with stops at some of the best restaurants in Chicago, where the city’s food scene shines with everything from deep dish pizza to fine dining. And when planning where to stay in Chicago, you’ll find options ranging from boutique hotels to convenient Airbnbs near the city’s top attractions. Whether it’s your first time visiting or a return trip like mine, Chicago is the perfect destination for a weekend getaway or a longer city escape.
