Top 11 Things To Do in Chicago This Weekend!

TravelLuxuryLiving
Travel Luxury Living
6 min readSep 12, 2023

The Windy City, Chicago, is a vibrant metropolis that never sleeps. It is easily accessible and boasts of an array of attractions that can keep anyone entertained for days on end.

From towering skyscrapers to world-renowned museums, Chicago has it all.

So, if you’re looking for some fun activities to do this weekend in Chicago, we’ve got you covered. In this post, we’ll explore the top 11 best things to do in Chicago to make your weekend a memorable one.

1. Visit the Chicago Cultural Center

The Chicago Cultural Center is located in the heart of the city and is home to a variety of free art exhibitions and events every week. It is the perfect spot to indulge in some culture, history, and art. Along with its spectacular architecture, the building is rich in history and has been around for over a century. So, why not explore this stunning building and some of the exhibitions this weekend?

2. See the City from Above

For some of the most amazing views of the city, head over to the Willis Tower Skydeck or the John Hancock Observatory. Both locations offer a bird’s-eye view of the city skyline, which is breathtaking, especially at sunset. So, get your cameras ready for some unforgettable selfie moments.

3. Get Lost in Nature

Millennium Park

Chicago is known for its beautiful parks, so why not take a stroll through the stunning Grant Park, the Millennium Park, or the Lincoln Park Zoo? These parks offer a plethora of activities, from picnicking to exploring fantastic artworks, fountains, and gardens to watching animals in the zoo. Also, Chicago’s Lakefront Trail is a beautiful place to take a walk, bike, or run. The trail stretches for 18 miles along Lake Michigan, offering stunning views of the water and the city skyline.

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4. Dine Out at Chicago’s Best Restaurants

Chicago is a culinary hub with a diverse range of dining options, from Michelin-starred restaurants to street food trucks. If you’re a foodie, you won’t be disappointed in Chicago. Some of the must-try dishes include deep-dish pizza, Italian beef sandwich, and Chicago-style hot dogs. So, plan your meals accordingly to savor the best of Chicago’s food scene.

5. Catch a Live Show

Chicago has a rich entertainment scene. Whether you prefer theater, comedy, or music, there’s something for everyone. Catch a Broadway show at the famous Chicago Theater or a comedy performance at The Second City. Or, if you’re in the mood for some concerts, check out the music venues like the Vic Theater and the Metro for live performances from top musicians.

6. Explore the Neighborhoods

Photo by Benoit Debaix on Unsplash

Chicago is made up of countless unique neighborhoods, each with its own culture and vibe. From the trendy shops and restaurants in Wicker Park to the historic architecture of the Loop, there is always something new to discover. Hit up a farmer’s market or check out an art fair to really get a feel for the local flavor.

7. Attend a Festival

Photo by Hanny Naibaho on Unsplash

No matter what time of year it is, Chicago is always home to a festival or two. Whether it’s the Taste of Chicago food festival, the Lollapalooza music festival, or the Lincoln Park Zoo’s annual ZooLights event, there is always something to celebrate in the city. Check out a festival this weekend to really get into the Chicago spirit.

8. Explore the Magnificent Mile

The Magnificent Mile is a shopper’s paradise with luxury boutiques, high-end department stores, and fashionable retailers lining the streets. The Magnificent Mile Lights Festival featuring a parade of Disney characters and fireworks is always a fun time for everyone. So, if you’re into shopping and entertainment, don’t miss the chance to explore the Magnificent Mile.

9. Visit Navy Pier

Located on the shores of Lake Michigan, Navy Pier is an iconic landmark offering a wide range of entertainment and recreational activities. From rides and games to boat tours and live music, Navy Pier has something for everyone. You can also enjoy stunning city views from Navy Pier’s observation wheel and indulge your taste buds at its restaurants and eateries.

10. Catch a Baseball Game at Wrigley Field

If you’re a sports fan, you can’t miss the opportunity to watch a Chicago Cubs game at Wrigley Field. Located in the Lakeview neighborhood, Wrigley Field is one of the oldest and most beloved ballparks in America. So grab some peanuts and beer and enjoy an amazing game in this iconic stadium.

11. Experience the Art Institute of Chicago

The Art Institute of Chicago is a world-renowned museum featuring an extensive collection of art from around the globe. It is particularly famous for its Impressionist and Post-Impressionist collections that include masterpieces by artists such as Monet, Van Gogh, and Renoir. So, if you’re an art enthusiast, make sure to add the Art Institute of Chicago to your itinerary.

From culture to history to stunning architecture, Chicago has something for everyone to enjoy this weekend.

So, grab your friends, family, or partner and explore the city with a plan to make memories that will last a lifetime. With this list of activity ideas, you’re sure to have a fun-filled weekend in the Windy City.

Have fun and make the most of your time in Chicago!

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That’s all for this list on the Top 11 Things to do in Chicago This Weekend!

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TravelLuxuryLiving
Travel Luxury Living

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