Imagine yourself exploring the vibrant streets of Chicago, experiencing a city that is bursting with excitement and enchantment. From breathtaking skyline views to mouthwatering deep-dish pizza, Chicago offers an array of unforgettable activities that will captivate your senses. Whether you’re looking to indulge in world-class art at the Art Institute, cheer on the Cubs at Wrigley Field, or dance the night away at one of the city’s lively jazz clubs, Chicago is a destination that promises to make memories that will last a lifetime. Get ready to embark on an unforgettable adventure as you discover the amazing activities that await you in the windy city.
Chicago, also known as the “Windy City,” is a bustling metropolis filled with endless opportunities for exploration and fun. From world-class museums to stunning views and mouthwatering local cuisine, there is something for everyone in this vibrant city. So pack your bags and get ready for an unforgettable adventure in Chicago!
Explore the World-Class Museums
The Art Institute of Chicago
The Art Institute of Chicago is a must-visit destination for art enthusiasts. With its extensive collection of over 300,000 artworks, including masterpieces by renowned artists such as Van Gogh, Monet, and Picasso, you will be immersed in a world of creativity and beauty. Whether you prefer Renaissance paintings, contemporary sculptures, or ancient artifacts, this museum has it all. Don’t forget to check out their special exhibitions and events for a truly enriching experience.
Museum of Science and Industry
Get ready to unleash your inner scientist at the Museum of Science and Industry. This interactive museum offers a wide range of exhibits that will educate and entertain visitors of all ages. From exploring a U-505 submarine to experiencing a simulated tornado, you will embark on a hands-on journey through various scientific wonders. Be sure to catch a show at the Omnimax Theater for a truly immersive cinematic experience.
Field Museum
Travel back in time at the Field Museum, where you can discover the wonders of natural history. Get up close and personal with Sue, the most complete Tyrannosaurus Rex skeleton ever found, and explore ancient civilizations in their Egyptian and Native American exhibits. With over 30 million artifacts and specimens, including the world-famous Evolving Planet exhibit, this museum is a treasure trove of knowledge and discovery.
Shedd Aquarium
Dive into an underwater paradise at the Shedd Aquarium. Housing over 32,000 animals from around the world, including dolphins, sharks, and penguins, this aquarium offers a mesmerizing glimpse into the wonders of marine life. From interactive exhibits to live shows, you will leave with a newfound appreciation for the ocean and its inhabitants. Don’t forget to catch a behind-the-scenes tour for a truly unforgettable experience.
Adler Planetarium
Embark on a journey through the cosmos at the Adler Planetarium. As America’s first planetarium, this iconic institution offers a wide range of exhibits and shows that will transport you to the outer reaches of the universe. Explore the wonders of space, learn about the latest discoveries, and even take a virtual trip to the moon. Whether you’re a space enthusiast or just curious about the cosmos, the Adler Planetarium is a must-visit destination.
Enjoy Spectacular Views from Skydeck Chicago
The Ledge
Get ready for an adrenaline rush at The Ledge, a glass box extending from the 103rd floor of the Willis Tower. Step inside and experience the breathtaking views of Chicago from 1,353 feet above the ground. Feel your heart race as you take in the panoramic vistas of the city skyline and Lake Michigan beneath your feet. Be sure to snap a photo for an unforgettable keepsake of your visit.
360 Chicago Observation Deck
If you’re looking for stunning views without the adrenaline, head to the 360 Chicago Observation Deck. Located atop the John Hancock Center, this observation deck offers a 360-degree view of the city. Enjoy a leisurely stroll around the deck and marvel at the beauty of Chicago from a different perspective. For an even more immersive experience, try TILT, a moving platform that tilts at an angle over the city for an unparalleled view.
Willis Tower Skydeck
No visit to Chicago is complete without a trip to the Willis Tower Skydeck. Ascend to the 103rd floor and prepare to be amazed by the cityscape sprawling before you. Step out onto The Ledge, a glass balcony that extends from the tower, and feel like you’re walking on air. With sweeping views of the city and beyond, this iconic attraction will leave you in awe of Chicago’s breathtaking skyline.
Cruise Along the Chicago River
Architectural Boat Tour
Discover the architectural wonders of Chicago on an exhilarating boat tour along the Chicago River. Cruise past iconic skyscrapers and historic landmarks, while knowledgeable guides provide fascinating insights into the city’s rich architectural heritage. From the towering Willis Tower to the iconic Wrigley Building, you’ll gain a deeper understanding of Chicago’s unique skyline.
Chicago’s First Lady Cruises
Experience the beauty of the Chicago River aboard Chicago’s First Lady Cruises. Glide along the water and take in the stunning views of the city’s architectural gems. With knowledgeable guides narrating the tour, you’ll learn about the history and significance behind each building. Don’t forget to bring your camera to capture the picturesque scenery that unfolds before your eyes.
Wendella Boats
For a truly immersive experience, hop aboard a Wendella Boat and cruise along the Chicago River. Whether you choose an architectural tour or opt for a sunset cruise, you’ll be treated to spectacular views of the city’s skyline. As you navigate the waterways, enjoy the gentle breeze and admire the towering buildings that have shaped the city’s landscape. Sit back, relax, and let the beauty of Chicago unfold before you.
Indulge in the Local Food Scene
Deep Dish Pizza
No trip to Chicago would be complete without indulging in the city’s famous deep-dish pizza. Sink your teeth into a thick, cheesy slice of this Chicago-style staple. With its buttery crust, chunky tomato sauce, and generous toppings, this pizza is a culinary delight that will satisfy even the heartiest of appetites. Whether you prefer classic toppings or adventurous combinations, there’s a deep-dish pizza for everyone to enjoy.
Chicago-style Hot Dogs
For a quick and delicious snack, grab a Chicago-style hot dog. This iconic street food is a true Chicago specialty, with its steamed poppy seed bun, all-beef frankfurter, and an array of toppings including mustard, relish, onions, tomatoes, pickles, and celery salt. It’s a flavor explosion in every bite. Head to one of the city’s many hot dog stands and experience this culinary delight firsthand.
Italian Beef Sandwiches
Sink your teeth into a mouthwatering Italian beef sandwich and experience a true Chicago classic. Thinly sliced roast beef is piled high on a crusty roll and topped with flavorful giardiniera or sweet peppers. Don’t forget to dip your sandwich in the savory au jus for an extra burst of flavor. Whether you enjoy it dipped or dry, this local favorite is sure to satisfy your taste buds.
Garrett Popcorn Shops
Satisfy your cravings for a sweet and savory treat at Garrett Popcorn Shops. This Chicago institution has been serving up delicious popcorn since 1949. Choose from their famous combination of caramel and cheese popcorn, or opt for other delectable flavors like butter, almond caramel crisp, and more. With its irresistible aroma and mouthwatering taste, Garrett Popcorn is a must-try snack in the Windy City.
Portillo’s
For a taste of Chicago’s culinary history, head to Portillo’s, a local favorite since 1963. Indulge in their famous Italian beef sandwiches, Chicago-style hot dogs, and mouthwatering burgers. Be sure to save room for dessert and treat yourself to their decadent chocolate cake or creamy milkshakes. With its retro atmosphere and delicious comfort food, Portillo’s is a beloved institution in Chicago.
Shop ’til You Drop on the Magnificent Mile
Michigan Avenue
Experience a shopper’s paradise on Michigan Avenue, also known as the Magnificent Mile. This iconic street is lined with a plethora of luxury boutiques, department stores, and renowned designer brands. From high-end fashion to exquisite jewelry, you’ll find everything you need for a stylish shopping spree. Take a leisurely stroll along this vibrant strip and indulge in some retail therapy amidst a backdrop of magnificent architecture.
Water Tower Place
For a one-stop shopping extravaganza, head to Water Tower Place. This multi-level mall offers a diverse range of shops and boutiques, from well-known brands to unique specialty stores. Whether you’re in search of fashion, beauty products, or home décor, you’re sure to find something that catches your eye. Take a break from shopping and grab a bite to eat at one of the many restaurants and cafes within the mall.
The Shops at North Bridge
Discover an unparalleled shopping experience at The Shops at North Bridge. With over 50 stores, including luxury retailers and trendy boutiques, this upscale mall offers a wide range of options for fashion enthusiasts. From designer clothing to accessories and cosmetics, you’ll find everything you need to elevate your style. After a day of shopping, unwind with a delicious meal at one of the mall’s fine dining establishments.
Catch a Live Performance at the Theater District
Broadway in Chicago
Experience the magic of theater at Broadway in Chicago. With multiple theaters showcasing a variety of shows, from Broadway hits to musicals and plays, you’re in for a night of entertainment like no other. Immerse yourself in the world of drama, comedy, and music as talented actors and performers take to the stage. Check the schedule for upcoming shows and make sure to book your tickets in advance for a memorable evening.
The Chicago Theatre
Step inside the iconic Chicago Theatre and prepare to be dazzled by its grandeur and history. Known as the “Wonder Theatre of the World,” this opulent venue has hosted legendary performances for over a century. Catch a live concert, comedy show, or theatrical performance in this architectural gem, and be transported to a world of entertainment and wonder.
Steppenwolf Theatre Company
For a unique and immersive theater experience, head to the Steppenwolf Theatre Company. Known for its innovative and boundary-pushing productions, this acclaimed theater company is a cornerstone of Chicago’s vibrant arts scene. From thought-provoking plays to daring performances, you’ll be captivated by the talent and creativity on display. Immerse yourself in the world of theater and witness the power of storytelling come alive.
Explore Navy Pier’s Entertainment and Attractions
Centennial Wheel
Discover breathtaking views of Chicago’s skyline and Lake Michigan aboard the Centennial Wheel at Navy Pier. As one of the city’s most iconic attractions, this towering Ferris wheel offers a bird’s-eye perspective of the city. Take a leisurely ride and marvel at the beauty that surrounds you. Whether you choose a daytime excursion or a romantic sunset ride, the Centennial Wheel guarantees a memorable experience.
Navy Pier IMAX Theatre
Immerse yourself in a larger-than-life cinematic experience at the Navy Pier IMAX Theatre. With its massive screen and state-of-the-art sound system, this theater promises an unforgettable movie-watching experience. Sit back and enjoy the latest Hollywood blockbusters or educational documentaries in stunning clarity and detail. From action-packed adventures to immersive nature films, there’s something for everyone at the Navy Pier IMAX Theatre.
Chicago Children’s Museum
For a fun-filled day with the little ones, head to the Chicago Children’s Museum at Navy Pier. With hands-on exhibits and interactive activities, children can engage in imaginative play and learning. From exploring a construction site to creating art masterpieces, there’s plenty to keep young minds entertained and engaged. Watch their faces light up as they embark on a journey of discovery and exploration.
Pepsi Wave Swinger
Experience the thrill of soaring through the sky on the Pepsi Wave Swinger at Navy Pier. This classic amusement ride takes you high above the ground, offering breathtaking views of Lake Michigan and the Chicago skyline. Feel the wind in your hair as you swing back and forth, creating unforgettable memories and laughter-filled moments. Whether you’re a thrill seeker or just seeking a fun experience, the Pepsi Wave Swinger is a must-try attraction.
Take a Stroll in Millennium Park
Cloud Gate (The Bean)
No visit to Millennium Park is complete without a visit to Cloud Gate, affectionately known as “The Bean.” This iconic sculpture, created by artist Anish Kapoor, is a mesmerizing reflection of the city skyline. Get up close and personal with this mirrored masterpiece and capture stunning photos as you see your reflection against the backdrop of Chicago’s skyscrapers. It’s a truly unique and unforgettable experience.
Lurie Garden
Escape the hustle and bustle of the city and immerse yourself in the tranquility of Lurie Garden. This enchanting oasis, located within Millennium Park, offers a respite from the urban landscape. Take a leisurely stroll through its lush greenery and vibrant blooms, and admire the intricate design that pays homage to Chicago’s natural landscape. Whether you’re looking for a moment of peace or a place to reconnect with nature, Lurie Garden is the perfect spot.
Jay Pritzker Pavilion
Experience live music and performances at the Jay Pritzker Pavilion, an architectural marvel nestled within Millennium Park. This outdoor amphitheater hosts a variety of concerts, festivals, and cultural events, offering a unique blend of nature and art. Pack a picnic and enjoy a free concert on the Great Lawn or reserve a seat for a ticketed event. From classical orchestral performances to contemporary music, this venue showcases a diverse range of talent.
Crown Fountain
Cool off on a hot summer day at the Crown Fountain, a playful water feature in Millennium Park. Designed by artist Jaume Plensa, this interactive installation features two 50-foot towers that project images of Chicagoans’ faces. As water cascades down the towers, visitors can gather around and splash in the shallow reflecting pool below. It’s a favorite spot for locals and tourists alike to relax, have fun, and beat the heat.
Attend Sporting Events in the Windy City
Chicago Cubs at Wrigley Field
Experience the excitement of America’s favorite pastime at Wrigley Field, home of the Chicago Cubs. Join thousands of passionate fans as you cheer on the team and soak up the electric atmosphere of the ballpark. From singing “Take Me Out to the Ball Game” during the seventh-inning stretch to enjoying classic ballpark snacks, a Cubs game is a quintessential Chicago experience that you won’t want to miss.
Chicago Bulls at United Center
Basketball fans won’t want to miss the opportunity to watch the Chicago Bulls at the United Center. Catching a game at this iconic arena is an exhilarating experience, from the pregame festivities to the thrilling action on the court. Join the sea of red and black as you cheer on the Bulls and witness the incredible athleticism of some of the NBA’s top players. Get ready for a night of high-flying dunks, impressive three-pointers, and passionate fans.
Chicago Blackhawks at United Center
For hockey enthusiasts, a Chicago Blackhawks game is a must-see event. Head to the United Center and witness the skill and speed of some of the NHL’s top players as they battle it out on the ice. From the thrilling sound of the puck hitting the net to the deafening cheers of the crowd, attending a Blackhawks game is an unforgettable experience that will make you feel like a part of the action.
Immerse Yourself in Chicago’s Music Scene
Chicago Symphony Orchestra
Indulge in the rich sounds of classical music with a performance by the renowned Chicago Symphony Orchestra. With its world-class musicians and captivating repertoire, this orchestra will transport you to the heart of the music. From symphonies by Beethoven and Mozart to contemporary compositions, their performances evoke a range of emotions and showcase the incredible talent of the musicians. Prepare to be moved by the power and beauty of live orchestral music.
Jazz and Blues Clubs
Chicago has long been hailed as the birthplace of jazz and an epicenter of the blues. Immerse yourself in the city’s vibrant music scene by visiting one of its legendary jazz and blues clubs. From intimate venues to lively bars, you’ll find the sounds of soulful melodies and toe-tapping rhythms filling the air. Watch as talented musicians captivate audiences with their improvisation skills and heartfelt performances. Whether you’re a jazz aficionado or a blues enthusiast, Chicago is the place to experience the magic of live music.
House Music History
Chicago has played a pivotal role in the evolution of house music, a genre that originated in the city’s nightclubs. Immerse yourself in the history and culture of this iconic genre by visiting clubs and venues that celebrate its legacy. From dance floors pulsating with infectious beats to DJ sets that keep the party going all night long, you’ll experience the energy and passion that make house music a cornerstone of Chicago’s nightlife. Dance to the rhythm of the city and let the music move your soul.
With its world-class museums, stunning views, delectable cuisine, and vibrant arts and music scene, Chicago offers a multitude of amazing activities that will leave you with unforgettable memories. From exploring the cultural treasures of its museums to indulging in local culinary delights, you’ll discover a city that is rich in history, creativity, and excitement. So grab your itinerary, pack your bags, and get ready to immerse yourself in all that Chicago has to offer.
