35 Things To Do in Chicago

By Janet Benoir – May 20, 2024

Welcome to Chicago, a city where towering skyscrapers meet the serene lakeside, creating a tapestry of architectural marvels and natural beauty. Chicago, often called the Windy City, offers a journey of discovery through its famous skyline and lively culture.

Let’s dive into the top 35 things to do in this magnificent city, each offering a unique slice of the Chicago experience.

Art Institute of Chicago

Begin your journey at the Art Institute of Chicago, a world-renowned museum where the halls echo with the whispers of artistic legends. This prestigious institution is not just a museum but a gateway to the worlds of countless artists, spanning centuries and continents. From the serene Impressionist paintings to the bold strokes of the Modernist era that challenge perception, the Art Institute is a visual feast that captivates and inspires.

Art Institute of Chicago

The museum’s commitment to education and public programs further enriches the experience, with lectures, workshops, and guided tours that invite deeper engagement with the art. Whether you’re a seasoned art aficionado or a curious newcomer, a visit to the Art Institute is a journey through the very heart of human creativity, where each piece tells a story waiting to be discovered.

Millennium Park and Cloud Gate

Stroll through Millennium Park, where art and nature blend seamlessly. This park is not just a green space; it’s a cultural meeting point where locals and tourists alike gather to experience the vibrancy of Chicago. From the enchanting Lurie Garden to the Jay Pritzker Pavilion, every corner of Millennium Park offers a unique experience.

Millennium Park and Cloud Gate

The centerpiece of Millennium Park is the Cloud Gate, an artistic marvel by the renowned British-Indian artist Anish Kapoor. This 110-ton elliptical sculpture mirrors the Chicago skyline and the clouds above in a way that seems almost surreal. Visitors are drawn to its 12-foot-high arch, allowing them to walk underneath and see their reflections in a funhouse mirror effect.

Chicago Architecture River Cruise

For a unique perspective of the city, embark on a Chicago River cruise. As you glide along the Chicago River, you’re greeted by an awe-inspiring panorama of architectural marvels. Each building tells its own story, from the majestic neo-Gothic design of the Tribune Tower to the soaring heights of the Willis Tower.

Chicago Architecture River Cruise

Witness the elegant Wrigley Building that lights up the riverfront, the historic Merchandise Mart once the largest building in the world by floor area, and the sleek contours of modern glass skyscrapers that reflect the sky and water. The guides provide engaging tales about the city’s past, from the Great Chicago Fire to the modern-day architectural renaissance.

Navy Pier

Navy Pier, a bustling hub of entertainment, extends into Lake Michigan like a welcoming arm. The centerpiece of the Navy Pier is the Centennial Ferris Wheel, an awe-inspiring structure that offers panoramic views of the city’s magnificent skyline and the vast lake. As you rise 200 feet above the ground in one of its gondolas, each turn provides a new perspective of Chicago’s architectural beauty and the shimmering lakefront.

Navy Pier

Shopaholics will delight in the myriad of stores and boutiques peppered along the pier, offering everything from unique souvenirs to high-end fashion. Navy Pier is also a cultural hotspot hosting an array of events throughout the year. From lively summer festivals to engaging winter activities and holiday celebrations, there’s always something happening at Navy Pier.

Willis Tower Skydeck

Elevate your Chicago experience, quite literally, at the Willis Tower Skydeck. As you journey upwards, the city’s streets and the bustle of urban life gradually shrink away, leaving you soaring amidst the clouds. The Willis Tower stands as a testament to the city’s architectural ingenuity and bold spirit. The Skydeck, located on the 103rd floor, provides an unparalleled 360-degree view of the cityscape, sprawling out in all its grandeur.

Willis Tower Skydeck

Upon stepping onto the Ledge, the Skydeck’s most thrilling feature, you’ll find yourself standing on a glass balcony extending out from the building’s façade. This heart-pounding experience gives you a clear, unobstructed view straight down, 1,353 feet to the streets below. It’s an exhilarating moment that blends fear and awe, as you float above the city like a bird in flight.

Shedd Aquarium

At the Shedd Aquarium, prepare to be captivated by a mesmerizing underwater universe. This aquatic haven is a sanctuary for over 32,000 marine animals, showcasing the incredible biodiversity of Earth’s waters. As you wander through the sprawling exhibits, you’ll encounter a stunning array of aquatic life – from the tiniest, vibrantly colored tropical fish darting through coral reefs to the imposing and graceful beluga whales.

Shedd Aquarium

What truly sets the Shedd Aquarium apart are its interactive and educational experiences designed to deepen your connection with the marine world. Engage in unique animal encounters where you can get up close with some of your favorite creatures. For those curious about what happens behind the scenes, the aquarium offers exclusive tours that provide a glimpse into the care and conservation efforts that go into maintaining this aquatic oasis.

The Field Museum

At The Field Museum, history comes alive. Here, the past is tangible, from the towering presence of SUE, the most complete Tyrannosaurus rex ever found, to the intricate details of life in ancient Egypt. Every exhibit is like a doorway to a different time and place, inviting you to explore the secrets of Earth’s and human history.

The Field Museum

The museum’s diverse exhibits cater to all curiosities, offering a glimpse into various realms of science and history. It’s a place where every corner reveals a new story, from the evolution of Earth’s biodiversity to the practices and beliefs of cultures long gone. This journey through time at The Field Museum is not just educational but a source of endless fascination and wonder.

Chicago Theatre

Step into the opulent Chicago Theatre for a night of entertainment. The theater, which opened in 1921, boasts a lavish French Baroque style, complete with elegant staircases, murals, and an exquisite lobby that harks back to the Roaring Twenties. A night here isn’t just about the show; it’s about immersing yourself in a piece of Chicago’s storied history.

Chicago Theatre

It’s here that legends of music, comedy, and drama have graced the stage, leaving audiences spellbound. The Chicago Theatre is a journey through time. Whether you’re catching a Broadway-caliber play, a stand-up comedy set, or a modern music concert, the magic of the past and the vibrancy of the present converge.

Lincoln Park Zoo

Lincoln Park Zoo is a verdant sanctuary nestled amidst the urban landscape of Chicago. This historic zoo, one of the oldest in the United States, invites you to a world where nature thrives amid the city. As you walk along the green paths, you’ll see a variety of animals, like impressive African lions and lively penguins, each living in areas made to look like their natural homes.

Lincoln Park Zoo

The beautifully landscaped grounds, complete with serene ponds and shaded groves, provide a perfect backdrop for a stroll or a family picnic. Throughout the year, the zoo hosts a variety of engaging events and programs, making every visit unique. Lincoln Park Zoo offers a delightful escape from the hustle and bustle of city life, free of charge, making it an ideal destination for visitors of all ages.

Chicago Riverwalk

The Chicago Riverwalk invites you on a tranquil journey amidst the bustling cityscape. Each step unveils stunning vistas of the city’s towering skyscrapers, mirrored in the gently flowing river. Art installations dot the walkway, offering a glimpse into Chicago’s vibrant art scene, while charming cafes beckon with the promise of a relaxing respite.

Chicago Riverwalk

This picturesque promenade is more than just a scenic route; it’s a hub of lively activity and cultural engagement. As the seasons change, so does the Riverwalk, offering ice sculptures in winter, blooming flowers in spring, and open-air dining in summer. It’s a place where locals and tourists alike gather to experience the pulse of Chicago in a uniquely beautiful setting.

Magnificent Mile

The Magnificent Mile on Michigan Avenue is a shopper’s dream, a vibrant stretch offering the essence of Chicago’s upscale shopping experience. Here, luxury and style converge with high-end boutiques and flagship stores from renowned designers and brands. You’ll find everything from the latest fashion trends to timeless classics, making it an ideal destination for those who seek a sophisticated shopping spree.

Magnificent Mile

Beyond shopping, the Magnificent Mile is an architectural marvel, boasting a blend of historic charm and modern splendor. The area’s gourmet restaurants and chic cafes offer delightful culinary experiences, perfect for refueling after a day of shopping. Whether it’s the allure of high fashion or the charm of historic landmarks, the Magnificent Mile offers an unforgettable experience that goes beyond mere retail therapy.

Wrigley Field

Sports enthusiasts can’t miss a visit to Wrigley Field, the legendary home of the Chicago Cubs. Feel the energy of passionate fans and catch a baseball game in this historic ballpark. Celebrated for its old-school charm, Wrigley Field, with its hand-operated scoreboard and distinctive red marquee, stands as a testament to the timeless allure of America’s pastime.

Wrigley Field

Immerse yourself in the game-day atmosphere that is as much about the experience as it is about the sport. Whether you’re a die-hard baseball fan or simply looking to enjoy a quintessential slice of the city’s culture, a visit to Wrigley Field is sure to be a home run. Witnessing the Cubs play is not just an activity but a memorable Chicago experience that resonates long after the last inning.

Adler Planetarium

Reach for the stars at the Adler Planetarium, where the cosmos comes alive in a spectacle of science and wonder. Situated on the scenic shores of Lake Michigan, this celestial haven offers a journey through the stars like no other. Step into the world of space exploration and experience the awe of the infinite universe, brought within your grasp.

Adler Planetarium

Inside the planetarium, interactive exhibits transport you across the galaxy. From touching a piece of the moon to navigating through distant galaxies, every exhibit is an opportunity to engage with the cosmos in a profound and personal way. The planetarium’s theaters, including the stunning Grainger Sky Theater, present awe-inspiring shows that blend cutting-edge science with storytelling magic.

Maggie Daley Park

Maggie Daley Park, nestled in the bustling heart of downtown Chicago, stands as a verdant oasis of joy and imagination. The park’s signature feature, a winding ice skating ribbon, offers a unique twist on traditional skating rinks. Skate along the winding path, enjoying the cool breeze, with the Chicago skyline in view.

Maggie Daley Park

The park’s playgrounds are a haven for children, with slides, swings, and climbing structures that inspire active play and imagination. For those seeking a peaceful retreat, the park’s numerous picnic spots and grassy knolls provide the perfect setting to relax and soak in the beauty of nature amidst the city’s dynamic energy.

Garfield Park Conservatory

The Garfield Park Conservatory, often referred to as “landscape art under glass,” is a verdant sanctuary nestled in Chicago’s urban landscape. Explore the conservatory’s eight rooms, each offering a unique environment – from the lush, tropical Palm House to the arid Desert House.

Garfield Park Conservatory

This is not just a visual delight; it’s an educational journey that tells the story of plants and their environments. Seasonal flower shows transform the Show House throughout the year, offering a kaleidoscope of colors and themes that celebrate the changing seasons. Additionally, the conservatory hosts various workshops and events, providing an interactive experience for visitors of all ages.

Chicago’s Lakefront Trail

Experience the allure of Chicago’s Lakefront Trail, a picturesque pathway that hugs the serene shores of Lake Michigan. This 18-mile trail is a blend of Chicago’s lively city scenes and peaceful nature. Ideal for cyclists, joggers, and walkers alike, each step or pedal along this trail offers a new perspective of the Windy City.

Chicago’s Lakefront Trail

The Lakefront Trail is where everyone comes to connect with the city uniquely. From bustling Navy Pier to the serene confines of the Promontory Point, the trail offers a diverse range of experiences, each a chapter in Chicago’s captivating story. Whether you’re seeking a vigorous workout or a tranquil stroll, the Lakefront Trail is a must-visit destination, inviting you to discover the heart and soul of Chicago.

The Green Mill

Step into the legendary Green Mill, a cornerstone of Chicago’s vibrant jazz scene, where history reverberates through its walls. This iconic jazz club offers more than just music; it’s a journey back in time. As you walk in, the vintage decor and dim lighting set the scene for an unforgettable night.

The Green Mill

As you settle into the plush seating, the world outside fades away, leaving only the rhythms of jazz to guide the evening. The lineup of performers ranges from seasoned pros to rising stars, each bringing their unique flair to the stage. Whether it’s a lively big band or a soulful solo act, the music here resonates with the heart of Chicago.

Museum of Science and Industry

The Museum of Science and Industry is where each exhibit unlocks a world of discovery and innovation. Imagine standing before a 40-foot tornado, feeling its power, yet safely exploring its mysteries. Here, each exhibit isn’t just to be seen but to be experienced. The museum is a playground for the mind, where interactive displays, from a mirror maze to a simulated tornado, make science an adventure.

Museum of Science and Industry

Each corner of the museum is a portal to a different time and place. It’s a place where the past meets the future, showcasing innovations that shaped the world and those that will shape tomorrow. The museum shows the amazing potential of the human mind, encouraging people to learn about science and imagine its future.

Chicago’s Comedy Scene

Chicago, known as the cradle of modern improvisational comedy, invites you to unravel your laughter in a city where comedy is a revered art form. Here, laughter echoes through historic halls where the likes of Tina Fey and Bill Murray honed their craft. It’s not just a show, it’s an experience where the vibrancy of Chicago’s spirit is encapsulated in every joke and jest.

Chicago’s Comedy Scene

As the spotlight hits the stage at the iconic Laugh Factory, prepare for an evening where chuckles turn into roaring laughter. Each performance is a mix of diverse comedic styles from observational humor to witty banter. In these hallowed spaces of hilarity, you’re not just an audience member. You become part of a community united by laughter, sharing the joyous essence of Chicago.

Deep-Dish Pizza

Deep-dish pizza is a must-try for food enthusiasts. With its thick, buttery crust, layers of cheese, and hearty tomato sauce, this pizza is an indulgent experience. Dive into a slice at one of the city’s legendary pizzerias and savor a taste of Chicago’s rich food culture. Each bite is a blend of flavors and textures, from the gooey mozzarella to the tangy sauce, all encased in a crispy, golden crust.

Deep-Dish Pizza

Whether you’re a pizza aficionado or a curious traveler, experiencing the rich, satisfying taste of Chicago-style deep-dish pizza is an unforgettable part of any visit to the Windy City. It’s not just food; it’s a piece of Chicago’s heart served on a plate.

Chicago’s Speakeasies

Venture into the heart of Chicago’s roaring twenties at its legendary speakeasies, where the spirit of Prohibition-era intrigue is very much alive. These hidden places, with their secret doors and entrances, take you back to a time of secret meetings. Once inside, you find a mix of old-fashioned charm and modern style.

Chicago’s Speakeasies

Whether it’s in a dimly lit, plush parlor or a cozy, jazz-infused nook, each speakeasy offers its unique twist on the allure of the past. Savor the flavors of carefully crafted drinks and soak in the atmospheric jazz melodies. In these hidden bars, you become part of the city’s vibrant, storied history.

Hot Tub Boat Cruise

Imagine cruising down the majestic Chicago River, the city’s towering skyscrapers looming above, while you’re nestled cozily in the warmth of a hot tub. As you embark on this one-of-a-kind journey, the chill of the Windy City is offset by the soothing warmth of the hot tub waters.

Hot Tub Boat Cruise

This hot tub cruise, a brainchild of The Chicago Electric Boat Company, transforms the river into a moving oasis of relaxation and luxury. Whether it’s a romantic evening, a unique celebration, or simply a new way to experience Chicago, the hot tub boat cruise promises an unforgettable adventure, blending the best of urban exploration with the ultimate in relaxation.

Pilsen Murals

Delve into the heart of Chicago’s Pilsen neighborhood, a vibrant street art that transforms every corner into a living gallery. This culturally rich enclave, known for its deep Hispanic roots, is an exhilarating explosion of color and expression. The art in Pilsen, with its impressive portraits of community figures and touching everyday scenes, strongly represents the neighborhood’s lasting legacy and impact.

Pilsen Murals

Artists here have turned the neighborhood into a dynamic forum, addressing issues close to their hearts and those of their community. These vibrant creations offer a unique perspective on the city’s character, reflecting the dreams and aspirations of generations. In Pilsen, every wall tells a story, making it a must-visit destination for anyone seeking to connect with the soul of Chicago.

Chicago’s Theater Scene

In Chicago’s theater scene, the stages come alive with performances ranging from Broadway smashes to cutting-edge experimental plays. Each theater reverberates with stories that captivate and inspire. As the curtains rise, audiences are transported into worlds of drama, comedy, and everything in between, showcasing the city’s rich tradition in the performing arts.

Chicago’s Theater Scene

The city’s deep-rooted theatrical history has bred generations of world-class talent. The Second City, a breeding ground for comedy legends, offers a night of laughter, showcasing the city’s unique brand of humor. Engage with thought-provoking pieces at the Lookingglass Theatre or get captivated by the innovative works at the Chicago Shakespeare Theater. No matter your taste, Chicago’s theater scene offers a window into the heart and soul of the city.

Chicago River

Kayaking on the Chicago River is not just an outdoor activity; it’s a journey through the lifeblood of Chicago. As you glide across the gentle currents, the river unfolds its story, showcasing the city’s architectural grandeur from an unmatched vantage point. The reflection of these impressive buildings on the river makes a captivating play of light and shadow, adding to the enjoyment.

Chicago River

This river adventure also reveals the city’s vibrant spirit. Along the banks, you’ll witness the hustle and bustle of urban life: joggers threading through riverside paths, locals enjoying a coffee break, and tourists capturing the moment. Whether it’s a sunny afternoon or a cool evening, kayaking on the Chicago River offers an intimate encounter with the heart of Chicago, making it an unforgettable experience for both visitors and locals alike.

360 CHICAGO Observation Deck

High above the streets, 360 CHICAGO offers panoramic views of the city and Lake Michigan. The deck is a gateway to the sky, offering an unparalleled perspective of the Windy City. The view from above changes constantly, showing Chicago in various colors during the day and night.

360 CHICAGO Observation Deck

Adding to the thrill is the TILT attraction, an adrenaline-pumping feature unique to 360 CHICAGO. Feel the rush as you tilt over the city, with only glass separating you from the scenes below. This exhilarating experience gives you a sense of flying, adding a dose of adventure to your sightseeing. It’s a moment where fear and awe blend seamlessly, offering a daring way to see the city.

The Loyalist

Nestled in the heart of Chicago, The Loyalist beckons food lovers with its reputation for serving one of the world’s best burgers. This culinary haven is an experience where the artistry of gourmet cuisine meets the comfort of classic American fare. As you step into this cozy, chic eatery, you’re greeted by an ambiance that is both welcoming and sophisticated, setting the stage for a memorable dining adventure.

The Loyalist

Crafted with the finest ingredients, these burgers feature a unique blend of innovative toppings and flavors that elevate them to a class of their own. This burger, with its delicious and well-cooked patty, fresh, high-quality buns, and a great mix of toppings, comes together to create a flavor that celebrates Chicago’s exciting food culture.

Chicago Cultural Center

The Chicago Cultural Center stands as a beacon of the city’s artistic heritage. This architectural marvel now dazzles visitors with its intricate mosaics, richly marbled halls, and the luminous glow of its two resplendent stained-glass domes. One of these, the Tiffany Dome, is the largest in the world and a masterpiece of design, casting a kaleidoscope of colors across the elegant interior.

Chicago Cultural Center

The center, much more than just a feast for the eyes, is a bustling hub of artistic and cultural activity. Whether it’s a thought-provoking lecture, a vibrant dance workshop, or a captivating film screening, the Chicago Cultural Center invites you to immerse yourself in the dynamic pulse of Chicago’s cultural heartbeat.

Chicago Botanic Garden

The Chicago Botanic Garden, a haven nestled away from the city’s hustle, stands as a testament to the beauty and diversity of nature. Spanning over 385 acres and home to 27 unique gardens and four natural areas, this living museum offers an enchanting escape.

Chicago Botanic Garden

Seasonal highlights like the stunning spring bulb display or the autumnal hues of the Maple Collection ensure that the Chicago Botanic Garden offers a fresh, breathtaking experience with every visit. Whether seeking solace, inspiration, or simply a day amidst the splendor of nature, the Chicago Botanic Garden is a jewel in Chicago’s crown, waiting to be discovered.

Buckingham Fountain

Nestled in the heart of Grant Park, this colossal structure, inspired by the Latona Fountain at Versailles, stands as an iconic representation of the city’s rich history and architectural prowess. As the water dances to the sky, reaching heights of 150 feet, the fountain becomes a living, moving piece of art. It’s a mesmerizing sight, especially during the evening.

Buckingham Fountain

During the warmer months, the fountain’s hourly water shows become a gathering spot for locals and tourists alike, making it a bustling hub of activity. Whether you’re basking in the spray on a sunny day or enjoying the illuminated spectacle at night, Buckingham Fountain offers a slice of Chicago’s charm and a moment of tranquility amidst the city buzz.

St. Patrick’s Day in Chicago

Experience the magic of St. Patrick’s Day in Chicago, a city that embraces the spirit of the Irish with a spectacle like no other. This special event is more than just honoring Irish culture; it’s a showcase of Chicago’s lively community and creativity. People, including locals and visitors, gather by the busy river to watch as environmentally friendly dye transforms the river into a bright green stream.

St. Patrick’s Day in Chicago

As the boats glide across the water, the river changes color right before your eyes, creating a perfect backdrop for photos and memories. This dazzling display is a symbol of the city’s ability to unite people from all walks of life in a shared moment of joy and wonder, solidifying it as one of Chicago’s most iconic and cherished traditions.

Lake Michigan Cruises

Set sail on the majestic Lake Michigan for an experience that marries tranquility with awe-inspiring views. Choose between a leisurely daytime excursion and a romantic evening sail under the stars. As the gentle waves carry you away from the hustle and bustle of the city, you’ll be treated to a stunning perspective of Chicago’s skyline.

Lake Michigan Cruises

On special occasions, the lake becomes a front-row seat to mesmerizing firework displays, painting the night sky with bursts of color. Whether you’re seeking a peaceful retreat or a romantic adventure, Lake Michigan Cruises provides a memorable and picturesque journey, encapsulating the essence of Chicago’s charm and elegance.

The Robie House

Located in the heart of Chicago, this iconic residence is more than just a building; it’s a manifestation of Wright’s groundbreaking approach to space, form, and light. The Robie House is celebrated for its horizontal lines that echo the flat, expansive Midwestern plains. The exterior, with its overhanging eaves and continuous ribbon of art glass windows, creates a stunning visual harmony with its surroundings.

The Robie House

The tour leads you through open, fluid interior spaces that break away from traditional Victorian compartmentalization, offering a glimpse into the future of modern architecture. Each room showcases creative design and forward-thinking, with features like overhanging balconies and detailed glass doors, blending living spaces with nature.

Rooftop Bars

Perched high above the bustling streets, Chicago’s rooftop bars are the epitome of urban elegance and style. Imagine sipping a finely crafted cocktail as the city’s iconic skyline sprawls beneath you, a panoramic view that stretches to the horizon. These rooftop havens are not just about the drinks; they are about the experience.

Rooftop Bars

As the sun sets, these chic venues come alive with ambient lighting, creating an atmosphere that’s both intimate and exhilarating. The city lights twinkle like stars below, setting the perfect backdrop for an unforgettable evening. Whether it’s a romantic date night or a lively gathering with friends, Chicago’s rooftop bars cater to every occasion.

Chicago Helicopter Tour

Soar above Chicago on a helicopter tour for a bird’s-eye view of the city. It’s an exhilarating adventure that showcases the beauty and scale of Chicago. Glide over iconic landmarks like Willis Tower, the shimmering waters of Lake Michigan, and the sprawling greenery of Millennium Park. As the helicopter sweeps across the cityscape, witness the architectural grandeur and urban energy of Chicago in a way that ground-level explorations can’t match.

Chicago Helicopter Tour

This helicopter tour is an unforgettable experience that captures the essence of Chicago’s magnificence. As the city unfolds below, each twist and turn reveals new wonders, from the intricate street patterns to the vast blue expanse of Lake Michigan. Whether bathed in the golden glow of sunset or sparkling with nighttime lights, Chicago’s skyline viewed from the skies is a sight to cherish.

Chicago, with its diverse attractions and vibrant culture, promises an unforgettable adventure. From its architectural marvels to its natural wonders, the Windy City offers a journey of discovery and excitement. Pack your bags and let Chicago’s charm and energy captivate your heart.