Header Notice

Winter is here! Check out the winter wonderlands at these 5 amazing winter destinations in Montana

25 Best Things To Do In Chicago, Illinois


Modified: January 3, 2024

by Nettie Crisp


Chicago, Illinois, is a vibrant and culturally diverse city that offers an endless array of activities and attractions for locals and visitors alike. From iconic landmarks to world-class museums, Chicago has something for everyone. Whether you’re a food lover, history buff, art enthusiast, or nature explorer, the Windy City has got you covered.

In this article, we will take a closer look at the 25 best things to do in Chicago. Whether you’re planning a weekend getaway or a longer stay, we have curated a list of must-see attractions and experiences that will make your trip unforgettable. So, get ready to embrace the hustle and bustle of the city, indulge in its mouthwatering cuisine, explore its rich history, and immerse yourself in its vibrant arts and culture scene.

Explore Millennium Park

One of Chicago’s most iconic landmarks, Millennium Park is a must-visit. Admire the famous Cloud Gate sculpture, also known as “The Bean,” take a leisurely stroll through the beautiful Lurie Garden, and catch a live concert at the Jay Pritzker Pavilion.

Visit the Art Institute of Chicago

Immerse yourself in the world of art at the renowned Art Institute of Chicago. Marvel at the vast collection of artworks, including masterpieces by famous artists such as Van Gogh, Monet, and Picasso.

Take an Architecture Boat Tour

Explore the city’s architectural wonders on a relaxing boat tour along the Chicago River. Learn about the history and significance of the city’s skyline while enjoying breathtaking views of iconic buildings like the Willis Tower and the Tribune Tower.

Indulge in Deep-Dish Pizza

A visit to Chicago wouldn’t be complete without trying the city’s famous deep-dish pizza. Head to one of the many renowned pizzerias and savor every gooey and cheesy bite of this iconic dish.

Enjoy Navy Pier

Navy Pier is a lively entertainment hub that offers a plethora of attractions, including rides, restaurants, shops, and even a Ferris wheel. Take a leisurely stroll along the waterfront and enjoy the stunning views of Lake Michigan.

Take in the Skyline from Willis Tower

Soar to the top of the Willis Tower, formerly known as the Sears Tower, and witness the breathtaking panoramic views of Chicago’s skyline. Step onto “The Ledge,” a glass observation deck that extends out from the building, for an exhilarating experience.

Explore the Magnificent Mile

Shopaholics rejoice! The Magnificent Mile is a shopper’s paradise, offering a wide array of luxury boutiques, department stores, and flagship brands. Take a leisurely stroll down this iconic stretch and indulge in some retail therapy.

Catch a Game at Wrigley Field

For sports enthusiasts, catching a game at Wrigley Field is a must. Cheer on the Chicago Cubs, one of the oldest baseball teams, and experience the electric atmosphere of this historic ballpark.

Discover the Shedd Aquarium

Dive into an underwater world at the Shedd Aquarium, home to a diverse range of aquatic species. Marvel at the magnificent beluga whales, watch playful dolphins, and learn about marine conservation efforts.

Experience the Field Museum

Embark on a journey through natural and cultural history at the Field Museum. Admire the impressive dinosaur skeletons, explore ancient Egyptian artifacts, and learn about different cultures from around the world.

Wander through Grant Park

Escape the hustle and bustle of the city by taking a leisurely stroll through Grant Park. Enjoy the tranquil surroundings, lush greenery, and picturesque views of Lake Michigan.

Dive into History at the Chicago History Museum

Uncover the fascinating history of Chicago at the Chicago History Museum. Explore interactive exhibits, learn about the city’s influential figures, and gain a deeper understanding of its cultural heritage.

Explore the Museum of Science and Industry

Ignite your curiosity at the Museum of Science and Industry, where hands-on exhibits and interactive displays bring science and technology to life. From space exploration to genetics, there’s something for everyone to enjoy.

Enjoy a Concert at Chicago Theatre

Experience the vibrant performing arts scene of Chicago by attending a concert or a theatrical performance at the iconic Chicago Theatre. With its stunning architecture and rich history, it’s a must-visit for any arts lover.

Discover the Chicago Riverwalk

Stroll along the scenic Chicago Riverwalk and soak in the picturesque views of the city’s skyline. Indulge in waterfront dining, enjoy live music performances, or simply relax and watch the boats go by.

Visit the Garfield Park Conservatory

Escape to a tropical paradise at the Garfield Park Conservatory. With its stunning botanical displays and lush gardens, it’s the perfect place to unwind and reconnect with nature.

Go on a Cubs Game Day Bar Crawl

Immerse yourself in the lively sports culture of Chicago by embarking on a Cubs Game Day Bar Crawl. Experience the excitement as fans gather to support their team while enjoying the city’s vibrant bar scene.

Explore the Lincoln Park Zoo

Spend a day in the company of exotic animals at the Lincoln Park Zoo. From lions and tigers to penguins and giraffes, this free zoo offers a memorable experience for visitors of all ages.

Enjoy a walk along the Riverwalk

Take a leisurely stroll along the scenic Chicago Riverwalk and enjoy the picturesque views of the city’s skyscrapers reflected in the water. It’s the perfect spot for a romantic sunset walk.

Visit the Chicago Cultural Center

Immerse yourself in art, music, and cultural events at the awe-inspiring Chicago Cultural Center. Admire the stunning architecture and explore the various galleries and exhibitions.

Try the Signature Chicago-Style Hot Dog

No visit to Chicago is complete without trying the city’s signature hot dog. Enjoy an all-beef hot dog served on a poppy seed bun and topped with mustard, onions, relish, pickles, tomatoes, and celery salt.

Experience the Adler Planetarium

Embark on a fascinating journey through space and astronomy at the Adler Planetarium. Explore immersive exhibits, attend captivating shows, and gaze at the stars through powerful telescopes.

Take a walk in Lincoln Park

Escape the city’s hustle and bustle with a leisurely walk in Lincoln Park. Enjoy the serene surroundings, lush greenery, and stunning views of Lake Michigan.

Discover the Museum of Contemporary Art

Immerse yourself in the world of contemporary art at the Museum of Contemporary Art Chicago. Explore thought-provoking exhibitions and witness the innovative works of both established and emerging artists.

Enjoy Live Music at The Green Mill

Step back in time at The Green Mill, a historic jazz club that has been entertaining audiences since Enjoy live music performances, sip on cocktails, and experience the vibrant atmosphere of Chicago’s jazz scene.

These are just a few of the 25 best things to do in Chicago, Illinois. With its rich culture, stunning architecture, and endless attractions, this city offers an unforgettable experience for every visitor. So, pack your bags and get ready to explore the wonders of the Windy City!


In conclusion, Chicago, Illinois is a vibrant city with a multitude of exciting things to do and see. From iconic landmarks to world-class museums, there is something for everyone in the Windy City. Whether you’re interested in exploring architecture, indulging in delicious food, or immersing yourself in the arts, Chicago has it all. Don’t miss the opportunity to visit famous attractions such as the Millennium Park, Navy Pier, and the Art Institute of Chicago. Take a stroll down the picturesque Magnificent Mile, catch a live comedy show, or experience the thrilling Navy Pier Ferris Wheel. Chicago truly has a unique charm and an incredible energy that will leave you with unforgettable memories. So pack your bags and get ready for an adventure-packed trip to the magnificent city of Chicago!


1. What are some must-visit attractions in Chicago?

Chicago offers a wide range of attractions, but some must-visit ones include Millennium Park, the Shedd Aquarium, Navy Pier, the Art Institute of Chicago, and the Willis Tower Skydeck.

2. Are there any free activities in Chicago?

Yes, there are plenty of free activities in Chicago. You can explore Millennium Park, visit the Lincoln Park Zoo, take a walk along the Lakefront Trail, or enjoy the street art in Wicker Park.

3. What are the best neighborhoods to explore in Chicago?

Chicago has many vibrant neighborhoods to explore. Some popular ones include the Loop, River North, Wicker Park, Lincoln Park, and the Gold Coast. Each neighborhood has its own unique character and offers a variety of dining, shopping, and cultural experiences.

4. What is the best time of year to visit Chicago?

The best time to visit Chicago is during the summer months (June to August) when the weather is warmer and many outdoor activities and festivals take place. However, spring and fall can also be great times to visit as the weather is mild and there are fewer crowds.

5. How can I get around Chicago?

Chicago has an extensive public transportation system including buses and trains, making it easy to get around the city. You can also use ride-sharing services, taxis, or rent a bike to explore the city.