Best Things to Do in Chicago: Top Attractions to Visit

Home to legendary sports teams, classic art museums, and stunning architecture, Chicago is a vibrant destination with a rich industrial history. Whether you’re a history buff, a nature seeker, or a partygoer, Chicago is full of culture and activities to keep you busy day and night. Not sure where to start? This guide will help you discover the best things to do in Chicago.

Iconic Attractions

You’ve all seen pictures. Every day visitors flock to attractions like Millennium Park’s Cloud Gate, the Willis Tower Skydeck, the city’s scenic river cruises, and more. Not sure where to start your tour of the windy city? We’re going to break down the city’s rich art museums, architecture, and other Chicago tourist attractions.

Visit Millennium Park

Millennium Park is a must for anyone exploring downtown Chicago. Known for Cloud Gate or “The Bean,” the park’s beautifully landscaped grounds are also home to free outdoor art installations and sculptures—not to mention the lesser-known Cloud Fountain.

💡 Did you know there’s even a hidden secret garden? With its unique blend of nature and its urban location, this hidden gem is a refreshing spot to recharge and explore. Don't miss this one-of-a-kind oasis!

Discover Navy Pier

The Navy Pier is one of Chicago's top attractions for family entertainment, featuring rides like the Centennial Wheel, along with dreamy views and boat tours of the lake. Perfect for a day of fun the whole family can enjoy. You might even discover your next favorite food vendor!

Admire the Art Institute of Chicago

Since the city is rich in history and cultural relevance, it’s no surprise that The Art Institute of Chicago is home to the work of some of the world’s most famous artists. Their world-class collection includes iconic masterpieces from Picasso and Vincent van Gogh. Perfect for art lovers, the museum is one of many must-see attractions in Chicago.

Experience Willis Tower

Experience panoramic skyline views from Willis Tower, one of the best ways to take in the entire city from above. The building is known for the iconic Skydeck or “The Ledge,” a treat for both fans of architecture and those trying to get the perfect Instagram shot of the skyline.

Walk Along the Magnificent Mile

The Magnificent Mile is a famous Chicago hotspot for shopping, chic restaurants, and anything else your heart may desire. Want a little more from your downtown dining experience? Try one of the many unique culinary experiences with top chefs, enjoy High Tea at the Astoria, or sign up for a wine tasting.

Natural Beauty

Chicago’s natural beauty is there for you to discover with serene rivers, parks, and nature for you and the family to explore. The best part? These leisurely activities are available for free.

💡 Did you know that Chicago has one of the largest urban parks in the U.S.? The city boasts over 8,800 acres of green space, including 600 parks, making it a haven for outdoor enthusiasts.

Relax by Lake Michigan

Why not spend the day at the beach? Lake Michigan’s lakes, beaches, and scenic walking trails highlight Chicago’s natural beauty. You can also rent a boat to take out on the lake at one of the many outposts.

Explore the Chicago River

The Chicago River flows through beautiful city skylines, passing some of the city’s renowned architecture. Another choice for a cultural experience is the Riverwalk, featuring multiple cafes, art installations, and restaurants for you to explore, making this exploration a truly unique thing to do in Chicago.

Visit Lincoln Park Zoo

Lincoln Park Zoo happens to be free for the entire family. Not only are the grounds home to a variety of animal species, but they are also a hub for family education with demonstrations to showcase animals’ cognitive abilities, the Houston Family Play Treehouse, Wild Sapling Play Forest, and a farm where kids can help care for animals.

Stroll Through Grant Park

Grant Park is Chicago’s pastoral hub where visitors and residents alike flock for a relaxing stroll along its many trails and gardens. The perfect place for an impromptu picnic, the park is also home to one of the largest fountains in the world, Buckingham Fountain.

Discover the Chicago Botanic Garden

The Chicago Botanic Garden is the perfect city hideaway for nature lovers, with an array of rare, vibrant flowers as well as lesser-known plants and trees. Seasonal displays are put on throughout the year to correspond with nature’s ever-changing beauty.

Cultural and Historical Sites

Chicago’s cultural and historical sites are a great way to learn more about the city’s rich history. The city’s renowned architecture and cultural institutions offer a variety of unique opportunities to learn more about art, natural history, and science.

Tour the Field Museum

The Field Museum is home to a variety of educational exhibits and programs, helping bring natural history to life for people of all ages. Touring the museum, you’ll visit Ancient Egypt, Volcanos, their dazzling gem collection, not to mention…dinosaurs.

Learn at the Shedd Aquarium

At the Shedd Aquarium, families can explore a variety of exhibits and interactive experiences featuring the Wild Reef, the ecosystems of the Amazon River, a jellyfish light display, and the Oceanarium—home to dolphins, sea lions, and beluga whales.

Ready to make a new friend? Stop by the touch pools to meet with real sea stars and sting rays.

Explore the Adler Planetarium

The Adler Planetarium’s educational shows and exhibits are bound to please any aspiring space explorer. Learn the science behind the stars, black holes, and the rest of the galaxy through a variety of interactive exhibits.

💡 Did you know that the Adler Planetarium was the first planetarium in the Western Hemisphere?

Attend a Show at the Chicago Theatre

A historic landmark since 1921, the Chicago Theatre is known for its stunning architecture, with its iconic marquee serving as one of the city’s most sought-after historical landmarks for photos. You can attend classic and contemporary Broadway productions as well as comedy shows and other special performances.

Visit Wrigley Field

Attend a game or sign up for a tour of the iconic Wrigley Field. You will experience the classic open-air stadium with its historic scorecard that is still hand-operated! A great place to visit for both sports enthusiasts and those looking to soak in the history of one of Chicago’s classic landmarks.

Must-Try Culinary Delights

Whether you're a devoted foodie or just hungry for something special, Chicago has your table waiting. Check out some of Chicago's top restaurants for an unforgettable (and maybe even photo-worthy) culinary experience.

The city has something for every foodie, whether you’re looking for a world-class dining experience or the charm of a local eatery.

Dine at Top Restaurants

Enjoy a multi-course tasting menu at Alinea, a self-described multi-sensory dining experience with an emphasis on artistic presentation methods—Michelin-starred, of course. If you’re looking for sustainable ingredients, seasonal, locally sourced tasting menus are available at Smyth, another restaurant devoted to unique food presentation.

Enjoy Local Food Tours

Ready to explore some of Chicago’s local specialties? A Chicago Pizza tour will not only include some of the best pizzerias, but you’ll also learn the history behind the city’s most famous dish. Want a little extra? Many companies offer citywide tours featuring all the classic dishes.

Explore the City's Diverse Cuisine

Chicago’s diverse food scene offers something for everyone. Not only will you find classic staples like deep-dish pizza and Chicago-style hot dogs, but also a wide blend of international, cultural favourites.

Family-Friendly Activities

Whether you want to make a splash at the aquarium, gaze upon the stars at the planetarium, or get grounded by learning about the earth’s natural history, there are multiple attractions for family fun.

Visit Family Attractions

Both the aquarium and the Field Museum offer hands-on interactive activities that combine entertainment and education. Places like Millennium Park and the Chicago Botanical Garden are also low-cost options for families to enjoy.

Enjoy Outdoor Parks

Chicago’s outdoor parks have been invested in significantly as part of a continued commitment to outdoor green spaces within the city. Both Millennium Park and Maggie Daley Park are examples of this investment, with the addition of art installations and interactive activities for the family.

Participate in Educational Tours

Both the Chicago Children’s Museum and the Chicago History Museum offer interactive tours and exhibits. Kids can participate in activities that range from learning about building structures to exploring a pirate ship.

Vibrant Nightlife

Exploring Chicago’s world-class nightlife venues is a must while visiting the city. Head downtown to enjoy popular spots like Smart Bar or to take in some jazz at the historic Green Mill Cocktail Lounge.

Explore Downtown Chicago

The city’s downtown core comes to life at night with the illumination of many iconic Chicago landmarks. From lively bars to late-night hotspots, the city’s dynamic nightlife is just steps away, ready for you to hit the dance floor!

Need a break? You can stroll past Millennium Park’s lit-up Crown Fountain or walk along the Chicago Riverwalk for stunning views of the glittering skyline.

Attend Music Shows

Why not take in a jazz and blues show at The Green Mill or Buddy Guy’s Legends? The city is also home to music festivals like Lollapalooza and the Chicago Blues Festival, both attractions that draw crowds from all over the world.

Discover Nighttime Attractions

Chicago nighttime views are taken to a whole new level from the 360 Chicago Observation Deck at John Hancock Center. Millennium Park’s lit-up landmarks and the Riverwalk’s gentle illumination are other popular Chicago experiences.

Unique Neighborhoods

Chicago neighborhoods are what gives the city its unique charm. Here’s your guide to these Chicago hotspots.

Explore the North Side

Chicago’s North Side is a must-visit area for sightseeing. You can head to Andersonville for eclectic dining and independent storefronts, or explore Old Town for its historic architecture. While in the north part of the city, you can visit the historic Wrigley Field or stop by the Lincoln Park Zoo for free.

Discover the West Side

Visit Pilsen for its colorful murals and other street art, authentic Mexican restaurants, not to mention the National Museum of Mexican Art. The West Loop is known for the trendy restaurants on Randolph Street—a vibrant atmosphere for the perfect evening out.

Walk Through Historic Downtown

Chicago’s downtown core is known for its architectural landmarks. Buildings like the Wrigley Building, Tribune Tower, and the Chicago Board of Trade each come with a rich history incorporated into their design.

Architectural Wonders

With iconic buildings like the Willis Tower and the John Hancock Center, the Chicago skyline is a must-see attraction for design enthusiasts and casual visitors alike.

Admire Iconic Buildings

Did you know the Willis Tower was once the tallest building in the world? Nearby, the Wrigley Building catches the eye with a remarkable, bright white façade, while the Aqua Tower impresses with its flowing balconies and sustainable features. These landmarks are just the beginning—explore our blog to discover more about the tallest buildings in Chicago!

Learn About Chicago's Architecture

The Chicago Architecture Center offers a variety of exhibits for all ages, helping visitors dive deeper into the city’s rich history. Their rotating exhibitions help architecture enthusiasts understand what goes into the construction of iconic buildings.

Take Architectural Tours

Want to see it all? Why not take a boat tour along the Chicago River to learn more about the design planning for significant buildings or an architecture tour of Chicago?

The Chicago Architecture Center also offers guided walking tours where you can explore stories behind the city’s most famous structures.

Planning Your Adventure

The key to every great vacation is planning! Make the most of your Chicago adventure by using this guide to prioritize the attractions that mean the most to you. You can explore travel options like river cruises, walking tours, or public transit to save money and make the most of your time.

Find the Best Travel Options

Chicago’s transportation system and rideshare services are great options for those on a budget. Hop on the CTA—Chicago’s robust public transit system—offering buses and trains. Prefer a more private ride?

Rideshares are everywhere, ready to whisk you to your next stop. For accommodations in Chicago, choose from numerous downtown hotels or a cozy Airbnb in one of Chicago’s trendy neighborhoods.

Check Out Seasonal Events

In the summer, Chicago is known for music festivals like the Chicago Blues Festival in June, and Lollapalooza in August. In the winter, there are a variety of Christmas activities like the Christkindl market. Make sure to check out local listings for more events and seasonal activities that might be happening.

Discover Hidden Gems

Chicago is filled with hidden gems you must see. Make time to discover the charming magical performances at the Chicago Magic Lounge or deepen your science and history knowledge at the International Museum of Surgical Science. There are plenty of options for a more intimate and off-the-beaten-path Chicago adventure.

Chicago: A City of Endless Possibilities

Looking for another unique experience to add to your trip? Why not check out our shows in Chicago? Our performances mirror the vibrance of the city’s culture with their own homage to theatre, artistry, and live music. In a city full of endless possibilities, it’s the perfect opportunity to explore new horizons.