Landmarks in Chicago: 12 You Don’t Want to Miss

With an abundance of landmarks in Chicago just waiting to be explored, it’s all too easy to feel lost and overwhelmed. It’s a challenge that can dampen the excitement and leave you second-guessing your choices.

Follow along as we unveil the 15 must-visit landmarks in the Windy City.

Prepare to be captivated, inspired, and awestruck as you immerse yourself in the vibrant tapestry of Chicago’s rich history and culture. Allow the Paris of the Prairie to steal your heart all over again. Or ignite a flame of love for the first time.

First, lace up those comfy kicks. Then, grab a slice of deep-dish pizza to fuel your journey. And finally, dive headfirst into a whirlwind of fun, discovery, and jaw-dropping sights! Let’s make every moment count!

Embark on an Extraordinary Journey through Chicago’s Landmarks

Millennium Park

Immerse yourself in the dynamic atmosphere of Millenium Park, where you’ll encounter a plethora of exhibits, outdoor artworks, captivating tours, and sensational concerts. This park is the beating heart of Chicago’s cultural scene, hosting an array of free events, activities, and festivals that are sure to leave you in awe.

Photo Alert: Grab your camera, strike a pose, and let the magic of “The Bean” unfold before your lens. Officially named “Cloud Gate,” the sleek, reflective surface and unique shape of this sculpture make it a photographer’s dream. Say cheese!

Delve deeper into the allure of Millennium Park by embarking on our Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck. With your own knowledgeable guide, you’ll explore famous Chicago landmarks including Millennium Park, while enjoying the panoramic vistas from the 360 Observation Deck.

It’s a tailored experience designed to make your visit to Chicago truly special. Trust us, you won’t want to miss it!

ground view of people walking past cloud gate bean in Millennium Park in Chicago, Illinois, USA
phot credit: Cloud Gate via Facebook

Willis Tower

Experience the thrill of standing atop the tallest building in Chicago, formerly known as the Sears Tower, now named Willis Tower. This towering icon once held the title of the tallest building in the world and continues to capture the imagination of visitors from around the globe.

Get ready to have your jaw drop as you ascend to the Skydeck Chicago, perched on the 103rd floor of Willis Tower. From this lofty vantage point, soak up the breathtaking panoramic views of the magnificent Chicago skyline that will leave you speechless.

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But hold onto your hats, because the excitement doesn’t stop there! Brace yourself for a heart-stopping moment as you step out onto “The Ledge,” an exhilarating feature of the Skydeck. This daring glass box extends 4.3 feet from the tower, giving you the sensation of floating in thin air.

It’s a thrilling adventure that allows you to witness the city sprawled beneath your feet, creating memories that will stay with you forever.

View looking up at The Willis Tower - Chicago, Illinois, USANavy Pier

Navy Pier is a cherished jewel along the shores of Lake Michigan, nestled between Illinois Avenue and Grand Avenue. This iconic Chicago landmark is a hub of endless fun, entertainment, and events, catering to visitors of all ages and interests.

At the heart of the Navy Pier stands the incredible Centennial Wheel, a symbol of adventure and awe. Step into one of the spacious enclosed gondolas and feel the anticipation build as you rise higher and higher.

From this elevated vantage point, you’ll witness the vast expanse of Lake Michigan sparkling beneath you and the city’s architectural marvels stretching into the horizon. Take in the sights and sounds of Navy Pier below, where laughter, music, and the joyful energy of visitors fill the air.

To fully appreciate the majesty of this landmark, don’t miss out on our Shoreline Sightseeing Boat Tour. Explore Lake Michigan’s scenic beauty, discover the endless wonders of Navy Pie, and learn about stories that whisper Chicago’s past.

view of Chicago skyline from lake Michigan with Navy Pier in Chicago, Illinois, USAChicago Riverwalk

Embark on a memorable journey along the scenic Chicago Riverwalk, a snap-worthy promenade stretching from Lake Shore Drive to Franklin Street. This picturesque pathway is a beloved destination known as the “Second Lakefront” among locals, offering a plethora of enticing attractions.

Marvel at the glistening waters of the Chicago River and the architectural wonders that line its shores. The riverwalk’s lush greenery provides a tranquil escape from the bustling city.

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Savor culinary delights, explore local artisans and stylish boutiques, embark on boat rentals for a tranquil cruise, and catch fun cultural events, including free concerts and exciting festivals.

Book our Chicago Riverwalk: Birthplace of Chicago Guided Tour to make the most of your visit to this landmark. Led by knowledgeable guides, this tour takes you on an interesting journey through time, unraveling the stories and secrets that make the riverwalk the birthplace of Chicago.

night view of lights on bridge in along riverwalk in Chicago, Illinois, USA
resized image

Wrigley Field

Step into baseball history at Wrigley Field, the cherished home to the Chicago Cubs. As one of the oldest MLB stadiums, Wrigley Field has witnessed countless legendary events, innovations, and traditions that have shaped the fabric of baseball history.

Fun Fact: In a remarkable recognition of its significance, Wrigley Field earned the prestigious designation of a National Historic Landmark in 2020. This rare honor, bestowed upon only a select few sites across the nation, solidifies Wrigley Field’s place in our country’s collective story.

Uncover more hidden gems and join our Scenic Chicago – North Side Tour. Discover the fascinating stories behind this iconic stadium and explore other historical Chicago landmarks that define the charm and allure of this city.

exterior view of wrigley field with crowd of people standing outside in Chicago, Illinois, USAJohn Hancock Building

John Hancock Building is a towering architectural gem in Chicago’s Magnificent Mile district. Standing at 1,128 feet and spanning 100 stories, this iconic supertall skyscraper, also known as 875 North Michigan Avenue, is a true Chicago landmark.

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Recognized for its architectural innovation, the John Hancock Building, affectionately called “Big John,” holds a special place in the city’s skyline and captures the hearts of its residents. With its mix of apartments, shops, offices, hotels, restaurants, and art galleries, it embodies the colorful spirit of Chicago.

While marveling at this architectural masterpiece is a must, why not take your Chicago experience to the next level? Embark on our Urban Adventure Cruise, where you can immerse yourself in the city’s energy while cruising along its iconic waterways.

Field Museum

Travel through time and space at the Field Museum, renowned as one of the premier natural history museums in the world. Immerse yourself in the wonder of more than 25 million historical artifacts, spanning the realms of dinosaurs, ancient civilizations, and beyond.

Among its prized treasures, the Field Museum proudly houses Sue, the largest and most complete Tyrannosaurus Rex ever discovered. You’ll never forget the first time you came face-to-face with a T.rex!

Pro Tip: If you plan to visit the Field Museum, make sure you have plenty of time in your schedule. With so much to see and experience at the museum, you do not want to rush through the exhibits.

People Walking up the steps to the Entrance of the Field Museum - Chicago, Illinois, USAAdler Planetarium

Explore the vast expanse of the universe and unravel the mysteries of the cosmos at the Adler Planetarium. This celestial haven is home to intriguing exhibits, state-of-the-art planetarium shows, and engaging interactive displays.

Step into the footsteps of astronomers and explorers who have shaped our understanding of the universe, and uncover the cutting-edge research and discoveries that continue to propel our knowledge forward.

Whether you’re a seasoned astronomer or a curious novice, the Adler Planetarium promises a truly enriching and one-of-a-kind adventure into the realms beyond our Earthly domain.

Combine the thrill of discovery at the Adler Planetarium with the panoramic views and expert commentary with our Big Bus Chicago Sightseeing Tours + Art Institute of Chicago Ticket Combo. It’s a comprehensive experience that encapsulates the essence of Chicago’s rich history, culture, and scientific marvels.

Cosmic wonder at adler planetariumShedd Aquarium

Dive into the underwater world of over 30,000 animals at the Shedd Aquarium. With its designation as a National Historic Landmark and unique architectural features, such as the Georgia marble-clad exterior, the aquarium exudes a sense of grandeur and timeless beauty.

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As one of Chicago’s most popular attractions, Shedd Aquarium welcomes over 2 million visitors each year. It offers an array of intriguing exhibits and experiences that cater to both young and old such as:

  • Stingray Touch
  • Amazon Rising
  • Wild Reef
  • Polar Play Zone
  • Caribbean Reef
  • Underwater Beauty
  • and Waters of the World

Beyond the exhibits, Shedd Aquarium offers an array of engaging activities. Take part in unforgettable animal encounters! Interact with fascinating sea creatures like penguins, beluga whales, or sea otters.

Consider purchasing the Go City Chicago All-Inclusive Pass to make the most of your Chicago adventure. This convenient pass grants you access to multiple landmarks in the city, including Shedd Aquarium. Providing a seamless and cost-effective way to explore the best of Chicago’s attractions.

Art Institute of Chicago

Experience the colorful world of art at the renowned Art Institute of Chicago. Located in the heart of downtown Chicago, the museum’s prime location invites visitors to indulge in the city’s rich cultural offerings.

With over 300,000 works of art, the Art Institute of Chicago boasts a vast and diverse collection. From paintings and sculptures to prints, drawings, and photographs. Every corner of the museum houses masterpieces that span different eras and genres.

Iconic works like:

  • Grant Wood’s American Gothic
  • Georges Seurat’s A Sunday on La Grande Jatte
  • Edward Hopper’s Nighthawks

grace the museum’s walls, enthralling visitors with their timeless beauty.

Whether you’re a family seeking an educational outing or someone simply interested in exploring the intersection of art and Chicago’s history. Book our Art Institute of Chicago Skip-the-Line Guided Tour! Make the most of your time and delve straight into the world-class art collection.

Wide shot of a group of women looking at the portraits of the Obama's at the Art Institute of Chicago in Chicago, Illinois
photo credit: Art Institute of Chicago via Facebook

Buckingham Fountain

As you stroll through Grant Park, witness the mesmerizing beauty of the Clarence F. Buckingham Memorial Fountain. This iconic landmark is a stunning tribute built in the 1920s. And was funded by Kate Buckingham in honor of her brother Clarence. Now, the Buckingham Fountain stands as a testament to their love for art and philanthropy.

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Marvel at the powerful jets of water shooting up to an impressive height of 150 feet. Creating a spectacle that will leave you in awe. And if you have the chance to visit in the evening, you’ll be treated to a magical sight as the water dances in sync with a dazzling light show. Adding an extra touch of enchantment to your experience.

Discover the allure of Buckingham Fountain. Along with other highlights that make Chicago truly extraordinary with our Best of Chicago Tour. Your expert guide will take you on a journey through the city’s most iconic landmarks and hidden gems. Showcasing the best of what Chicago has to offer.

outdoor of buckingham fountain in Chicago, Illinois, USA
The Buckingham Fountain was featured in the opening credits of the “Married…With Children” TV show.

Lincoln Park Zoo

Have you noticed that the landmarks in Chicago all seem to have a rich history? The Lincoln Park Zoo is no exception. Established in 1868, this beloved landmark stands as one of the oldest zoos in the United States.

The best part? From playful armadillos to majestic polar bears, you’ll have the opportunity to immerse yourself in the wonders of the animal kingdom for FREE. That’s right—entrance to this amazing attraction won’t cost you a dollar!

The Lincoln Park Zoo is not just a place to observe wildlife; it’s an opportunity to connect with nature. Learn about conservation and foster a deeper appreciation for the remarkable creatures that share our planet.

Pssst…wanna explore Chicago without breaking the bank? Who doesn’t? Introducing our exclusive Chicago Explorer Pass Package, your ticket to experience the best of the Windy City while enjoying incredible savings.

With this package, you’ll gain access to a handpicked selection of the city’s most popular attractions and landmarks at a discounted price. Whether you’re interested in exploring world-class museums, taking architectural tours, or immersing yourself in cultural experiences, this pass is all that you need.

Lions in the Lincoln Park Zoo in Chicago, Illinois, USA
photo credit: Lincoln Park Zoo via Facebook

Start Crafting Your Perfect Chicago Adventure Today

Plan your Chicago Illinois getaway now with Tripster’s Hotels, Attractions, and Vacation Packages. Creating a personalized itinerary that reflects your unique taste.

Whether you’re yearning for Millennium Park’s captivating allure, the Adler Planetarium’s cosmic wonders, or the wild adventures at Lincoln Park Zoo, we’ve got you covered every step of the way.

So, why wait? Grab your sense of adventure! Pack your bags! And let Tripster be your guide to the enchanting world of Chicago landmarks. The Chi-town is calling, and your perfect adventure awaits!

Tell us, What Landmark Chicago Did We Miss?

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Written by Archie Villaflores

Over the years, he has won numerous national contests for news and editorial writing, but he has recently discovered that his true passion...

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