Welcome to the magnificent city of Chicago, where adult adventurers find a playground of cultural richness, culinary delights, and endless entertainment.

As a dedicated traveler and explorer, I am thrilled to present a comprehensive guide to 35 captivating things to do in Chicago for adults.

This bustling metropolis offers a diverse range of experiences that cater to every taste and interest.

Whether you’re a local looking to spice up your weekends or a visitor seeking memorable moments, this guide will help you unlock the treasures of Chicago’s vibrant adult scene.

1. Art Institute of Chicago

Unearth the artistic gems at the Art Institute of Chicago. From renowned classics to contemporary works, this museum offers a captivating journey through the world of art.

The Art Institute of Chicago is a beacon of artistic brilliance, housing some of the greatest works ever created by humankind.

From antique masterpieces to modern-day innovations, this iconic museum boasts a collection that stirs the soul and enlightens the mind. 

Discover Renaissance paintings such as da Vinci’s Virgin and Child with Saint Anne, or take in the bold strokes of Claude Monet’s Sunflowers

2. Navy Pier

Explore Navy Pier, a bustling hub of entertainment. Enjoy rides, dine at waterfront restaurants, shop for souvenirs, and catch breathtaking lake views.

Navy Pier is Chicago’s premier waterfront destination, featuring a vibrant mix of shopping, dining, entertainment, and breathtaking lake views.

Visitors can soak in the atmosphere with a variety of rides, from family-friendly attractions to thrilling rollercoasters and Ferris wheels.

Those looking to relax can take in stunning vistas from atop the iconic Centennial Wheel or enjoy a leisurely stroll amidst endless shops and kiosks offering unique souvenirs and memorabilia.

3. 360 Chicago: Sky-High Thrills and Views

Take the elevator ride to 360 Chicago for unparalleled views of the city. Stand on “The Ledge,” a glass box extending from the building, for an adrenaline rush like no other.

If you’re looking for a thrilling experience with unbeatable views of the city, then 360 Chicago is the place for you.

This spectacular observation deck is located atop John Hancock Center in the heart of downtown Chicago. Take the elevator up 94 floors and be prepared for awe-inspiring sights from every angle.

Once you’ve reached the top, step outside onto The Ledge: four glass boxes resting atop the building that provide visitors with unobstructed views of the streets below. 

4. Lincoln Park Zoo

Embrace nature at Lincoln Park Zoo, a free attraction offering the chance to see exotic animals in a beautiful park setting.

The Lincoln Park Zoo is a wonderful opportunity to experience the wonder of nature in a unique and free setting.

Step inside this lush and beautiful park, and you’ll be surrounded by a vast array of exotic animals from all over the world.

5. Chicago Riverwalk

Stroll along the Chicago Riverwalk, where you can find charming cafes, river cruises, and art installations amidst stunning urban scenery.

The Chicago Riverwalk is an urban oasis that beckons visitors from near and far. Stretching along the Chicago River, the riverwalk features cafes, cruises, and art installations amidst a stunning backdrop of skyscrapers. It’s the perfect place to unwind and explore Chicago’s unique flavor.

Take a stroll to enjoy picturesque views of the iconic Willis Tower, or wander through popular attractions such as Marina City and the historic Water Tower Place.

You can also take advantage of the riverwalk’s convenient access to ships offering sightseeing tours and dinner cruises.

6. Wrigley Field: Catch a Cubs Game

Experience the thrill of a Chicago Cubs game at historic Wrigley Field. The atmosphere here is electric, making it a must for sports enthusiasts.

Wrigley Field is a place like no other. Steeped in history, this iconic baseball stadium has been home to the Chicago Cubs since 1914 and continues to attract sports fans from all over the world.

When you step through the gates of this legendary ballpark, you’ll be greeted by the thunderous roar of the crowd, the smell of popcorn and hotdogs, and the unmistakable feeling that you’ve stepped into something quite special.

Whether you’re a passionate fan or just looking for a fun way to spend an afternoon, catching a game at Wrigley Field guarantees a unique and unforgettable experience. From the ivy-covered walls to the handcrafted statues outside the park, every detail of this venue oozes with charm and nostalgia. But what really shines here is the vibrant atmosphere, created as much by the passionate fans as it is by the players on the field. So grab your tickets and join in the excitement — because watching the Chicago Cubs play at Wrigley Field is something you won’t want to miss.

7. Second City Comedy

Catch a comedy show at The Second City, a renowned improv and sketch comedy club that has produced some of the world’s most famous comedians.

The Second City is a renowned comedy club located in the heart of Chicago. Its unique blend of improv and sketch comedy has made it a favorite venue for many audiences, including those who enjoy classic theater and modern stand-up.

Founded in 1959 by Neil Levenson and Bernie Sahlins, The Second City has been a hotbed of comedic talent for over six decades.

8. Museum of Science and Industry

Delve into the wonders of science at the Museum of Science and Industry. Engaging exhibits cater to adults’ curiosity and fascination.

The Museum of Science and Industry is an incredible place to let your curiosity take flight. Visitors of all ages can explore the wonders of science through exciting exhibits, interactive demonstrations, and informative lectures.

9. The Magnificent Mile

Indulge in world-class shopping along The Magnificent Mile. From luxury boutiques to department stores, it’s a retail paradise.

Experience one of the world’s top shopping destinations — The Magnificent Mile! Here, you’ll find a range of retail options to explore.

From luxury boutiques featuring designer labels to stores offering more budget-friendly wares, there’s something for everyone.

10. Shedd Aquarium

Explore aquatic wonders at Shedd Aquarium. Get up close to dolphins, beluga whales, and countless other marine species.

Shedd Aquarium is a must-see destination for anyone looking to explore the fascinating undersea world. Here, you can get up close to dolphins, beluga whales, and countless other marine species in their natural habitats.

Observe exotic fish swim gracefully through towering coral reefs or take in live educational presentations about the conservation of endangered species.

11. Millennium Park

Visit Millennium Park for iconic attractions like Cloud Gate (The Bean) and free concerts at the Jay Pritzker Pavilion.

Millennium Park is one of Chicago’s most popular attractions, located in the heart of the city. Guests can explore a variety of attractions, such as Cloud Gate (The Bean), a 110-ton elliptical sculpture made of polished steel plates that reflects the skyline and creates an unforgettable landscape.

12. Chicago Symphony Orchestra

Enjoy the harmonious sounds of the Chicago Symphony Orchestra at Symphony Center, where world-class performances come to life.

The Chicago Symphony Orchestra is one of the foremost symphony orchestras in the world. Founded in 1891, the orchestra’s mission has been to bring great music to life through performance and education.

At Symphony Center, audiences can enjoy an evening of thrilling performances from some of the greatest musicians around.

13. Chicago Botanic Garden

Escape to the Chicago Botanic Garden for serene landscapes, stunning gardens, and a respite from urban life.

The Chicago Botanic Garden is the perfect destination for an escape from the hustle and bustle of the city. It offers a tranquil haven with breathtaking gardens, meandering trails, and lush green spaces.

Get lost in the natural beauty of the garden’s 25 immersive displays, including woodland, prairie, and aquatic gardens.

14. Historical Walking Tours

Partake in historical walking tours to discover Chicago’s rich history, from the Great Chicago Fire to the Prohibition era.

Discover the vibrant history of Chicago on a historical walking tour! Uncover tales of intrigue, scandal, and triumph as you traverse the footsteps of some of the city’s most renowned figures.

Trace the path of the Great Chicago Fire and visit sites where the Prohibition era was at its height.

15. Live Jazz at Green Mill

Savor live jazz performances at Green Mill Cocktail Lounge, a legendary venue steeped in musical history.

Green Mill Cocktail Lounge is an iconic jazz venue that has long been considered a hotspot for music lovers.

Located in Chicago, Green Mill has earned itself a reputation as one of the premier destinations to experience live jazz performances.

16. Chicago Theatre District

Experience Broadway-style shows and world-class performances in Chicago’s Theatre District. Welcome to the vibrant and exciting Theatre District in downtown Chicago!

Home to some of the best theaters in the country, the Theatre District is well-known for its spectacular shows and premier performances.

The theater district also has a great selection of restaurants, shops and other amenities to enhance your theatergoing experience.

So whether you’re here to see a show or just want to explore all that the district has to offer, plan a visit to Chicago’s Theatre District today!

17. Culinary Delights

Embark on food tours and tastings to savor the city’s diverse culinary scene, from deep-dish pizza to gourmet hot dogs.

Experience the best of Chicago’s culinary scene with a guided food tour! From deep-dish pizza to gourmet hot dogs, you’ll get to sample all the iconic eats the city has to offer.

Get ready for an adventure that will tantalize your taste buds and leave you wanting more.  

Our tours give you an inside look at the diverse flavors of Chicago, letting you explore the city through its cuisine.

18. Chicago Architecture Cruise

Take an architectural river cruise to learn about Chicago’s iconic skyscrapers and architectural history.

Explore the majestic skylines of Chicago with an architectural river cruise! Get up close and personal with some of the city’s most iconic skyscrapers and explore its rich architectural history.

19. Graffiti Art in Pilsen

Explore the vibrant street art scene in Pilsen, where colorful murals adorn the neighborhood’s walls.

Pilsen, a neighborhood on Chicago’s southside, is home to a vibrant street art scene that has been rapidly growing in popularity.

With its bright colors and unique styles, the innovative graffiti art found in this area is sure to draw the eye of any passerby.

From political murals advocating for justice and change to more whimsical works depicting wild animals or mythical creatures, the range of artwork on display here is truly remarkable. 

20. Chicago Cultural Center

Discover the Chicago Cultural Center’s beautiful architecture and ongoing cultural exhibitions and events.

The Chicago Cultural Center is a true testament to the city’s vibrant culture and history. Located in the heart of downtown, this impressive building is steeped in architectural grandeur, featuring stunning stained glass windows, custom-built mosaic floors, and intricate woodwork—all of which make it one of the most iconic landmarks in the Windy City. 

In addition to its architectural splendor, the Chicago Cultural Center houses numerous rotating exhibitions and events.

21. International Museum of Surgical Science

Uncover the history of surgical science at this intriguing museum housed in a historic mansion.

The International Museum of Surgical Science is located in a majestic building, originally built in 1909 by Potter Palmer. This museum offers visitors a unique chance to explore the history of surgical science and its many achievements over the centuries. 

At the museum, you can tour the galleries which feature a variety of exhibits that illustrate the evolution of medical tools and techniques over time.

22. Chicago River Kayak Tours

Paddle through the Chicago River on kayak tours, offering a unique perspective of the city’s architecture.

Life in Chicago can be a whirlwind of activities and sights, but why not slow down for a while and take in the city from an entirely different perspective?

Join us on one of our Chicago River Kayak Tours and uncover the beauty of the iconic skyline and historical architecture as you paddle through the heart of the city.

Our certified instructors will teach you basic kayaking techniques before heading out onto the river, leaving you fully prepared to explore the waterside parks, bridges, and landmarks that line the route. 

23. Chinatown Exploration

Immerse yourself in the rich culture of Chicago’s Chinatown with authentic cuisine and shopping.

Discover the vibrant culture of Chicago’s Chinatown, where ancient traditions mingle with modern lifestyles.

Taste delicious dishes from street vendors and restaurants alike, exploring the many flavors of Chinese cuisine.

24. Money Museum at the Federal Reserve: 

Learn about economics and currency at the Money Museum, where interactive exhibits shed light on financial matters.

The Money Museum at the Federal Reserve is the perfect place to explore the world of economics and currency.

With interactive exhibits, visitors can gain a better understanding of how money works and its role in today’s economy.

25. Chicago Distillery Tours

Explore local distilleries on guided tours and learn about the art of craft spirits production. Discover the fascinating world of craft spirits on a guided distillery tour in Chicago.

Our experienced guides will take you to some of the city’s most distinguished distilleries, giving you exclusive access to their renowned facilities as well as insight into their production process.

26. Jazz Showcase

Experience legendary jazz performances at the Jazz Showcase, a venue that has hosted jazz icons.

The Jazz Showcase has been a beacon for jazz enthusiasts since its inception in 1947. As one of the oldest and most iconic venues dedicated to the style, it is home to some of the most legendary jazz performances of all time.

27. City Parks

Enjoy picnics and relaxation in Chicago’s beautiful city parks, offering a peaceful escape. Chicago is home to many beautiful city parks, offering a peaceful outdoor escape for those looking to enjoy the city from a different perspective.

From sprawling green spaces like Humboldt Park and Grant Park to hidden urban oases such as Garfield Park Conservatory and Lincoln Park Zoo, each park offers its own unique atmosphere, whether you’re in the mood for a relaxing picnic or an afternoon of exploration.

28. Nightlife in River North

Discover the vibrant nightlife scene in River North, known for its bars, clubs, and entertainment.

Visitors to River North in Chicago will find a vibrant nightlife scene to explore. This neighborhood is renowned for its many bars, clubs, and other entertainment venues offering a variety of options for those with diverse interests. 

Whether you’re seeking a relaxed evening with friends or a more rowdy atmosphere, there is something here to fit any mood.

29. Ghost Tours

Take a ghost tour to explore Chicago’s haunted history and hear spine-tingling stories. Do you love the thrill of a good spooky story?

Are you eager to uncover the hidden secrets of Chicago’s past? If so, then a ghost tour is the perfect activity for you! On a ghost tour, you’ll delve into Chicago’s haunted history and learn about some of its most mysterious and spine-tingling tales.

30. Chicago Beaches

Relax at Chicago’s beaches along Lake Michigan, perfect for sunbathing and swimming.. For those looking for a peaceful escape from the hustle and bustle of the city, there’s no better option than the gorgeous beaches of Lake Michigan.

Located just a short drive away from Chicago’s downtown, these stunning beaches are perfect for sunbathers, swimmers, and anyone seeking to relax in the city’s refreshing lakeside atmosphere. 


I hope this comprehensive guide has inspired your journey through Chicago’s vibrant adult offerings. Whether you’re a local looking for new adventures or a visitor seeking to explore the city, Chicago’s diverse attractions cater to every taste.

Share your thoughts and experiences in the comments below, and encourage others to embark on their own adult adventures in the Windy City.