Excited for Chicago but not sure where to start? Fear not, travelers! This guide unveils Chicago’s Top Tourist Landmarks—the crown jewels you can’t miss. But wait, there’s more! We’ll also sprinkle in some under-the-radar delights for those seeking an escape from the typical tourist trail.

This bustling metropolis is a treasure trove of must-see destinations, from the iconic Navy Pier to the historic Wrigley Building. Whether it’s your first visit or you’ve been here before, get ready to be amazed by the fascinating history and lively culture that make these famous places so special. 

So, gear up and get ready to immerse yourself in the rich tapestry of culture, history, and architectural wonders that define the essence of Chicago’s top tourist landmarks.

Let’s dive in and discover the magic of the Windy City!

Chicago’s Top 10 Tourist Landmarks 

Yearning for breathtaking skylines and iconic sights? Then dust off your walking shoes because Chicago’s top 10 tourist landmarks are calling your name. This dynamic metropolis promises an unforgettable adventure, from architectural marvels to artistic treasures.

So, strap in and prepare to be dazzled as we unlock the Windy City’s hidden gems and must-see wonders. Dive into Chicago’s top tourist landmarks and let the Windy City work magic. Don’t let this opportunity slip away—get your hands on the Chicago Travel Guide today!

1. Millennium Park

Millennium Park - Chicago's Top Tourist Landmarks
Millennium Park, Chicago


Michigan Ave, Columbus Dr, & Monroe St border Downtown Heart.

Overview of Millennium Park

Millennium Park, a must-visit for any Chicago tourist, boasts iconic art, stunning gardens, and year-round events. Snap a distorted selfie under “The Bean,” cool off at Crown Fountain’s interactive spouts, and catch a free concert on the Great Lawn. Be aware of construction around “The Bean” until spring 2024.

Entry Fee

Good news! It’s completely free to enter Millennium Park.

Key attractions 

Millennium Park is home to a variety of key attractions, including:

  • Cloud Gate (The Bean): A stainless steel sculpture by Anish Kapoor, Cloud Gate is one of the most popular tourist attractions in Chicago. The sculpture’s reflective surface allows visitors to see themselves and the city skyline in a distorted way.
  • Crown Fountain: A video sculpture by Jaume Plensa, Crown Fountain consists of two 50-foot-tall glass towers that project images of water-spouting faces. Visitors can walk through the water in the fountain’s reflecting pool on hot days.
  • Jay Pritzker Pavilion: A free outdoor concert venue designed by Frank Gehry, the Jay Pritzker Pavilion hosts a variety of musical performances throughout the year.
  • Lurie Garden: A two-acre public garden designed by Piet Oudolf, Lurie Garden features a variety of native plants and flowers. The garden is a popular spot for visitors to relax and enjoy the outdoors.
  • BP Bridge: A pedestrian bridge designed by Frank Gehry, the BP Bridge connects Millennium Park to Maggie Daley Park, another popular park in the Loop neighborhood.

2. Cloud Gate

Cloud Gate - Chicago's Top Tourist Landmarks
Cloud Gate, Chicago

Chicago’s iconic Cloud Gate, affectionately nicknamed “The Bean,” beckons. But before you strike a pose, here’s the latest lowdown:


Nestled within Millennium Park, bordered by Michigan Ave, Columbus Dr, & Monroe St.

Overview of Cloud Gate

Cloud Gate weighs 110 tons and measures 66 feet long, 33 feet high, and 42 feet wide. The sculpture’s mirror-like surface is regularly polished to maintain its flawless reflection. Beneath the sculpture, you’ll find a concave chamber known as the “omphalos,” which offers an intriguing perspective of the underside of The Bean. While Cloud Gate is undergoing construction until spring 2024, there’s still plenty to experience in Millennium Park, a top Chicago landmark! Cloud Gate’s unique reflection magic can still be experienced from surrounding areas.

Entry Fee

Entry to Millennium Park and to view Cloud Gate from afar is completely free!

Key attractions 

  • Mirror Mania: Distorted reflections of Chicago’s skyline & yourself below the Bean’s polished surface.
  • Funhouse Fun: Crawl under the arch for warped selfies & playful interactions with your reflection.
  • Iconic Status: A beloved symbol of Chicago & must-see for any Windy City visitor.
  • Park Paradise: Surrounded by greenery & art in Millennium Park for a pleasant atmosphere.
  • Free & Fun: Enjoyable for all ages without costing a dime.

3. The Magnificent Mile

The Magnificent Mile Chicago
The Magnificent Mile, Chicago

Dive into the dazzling world of Chicago’s Magnificent Mile, a must-visit on any Windy City adventure. But before you whip out your credit card, here’s the insider scoop:


Spanning North Michigan Avenue from Oak Street to Chicago River 

Overview of Magnificent Mile

The Magnificent Mile caters to every whim, from luxury shopping sprees to cultural explorations and mouthwatering meals. It’s more than just a shopping haven; it’s a vibrant artery of Chicago’s heart, offering something for everyone. Plus, its proximity to Millennium Park allows you to seamlessly blend art, nature, and retail therapy into your itinerary.

Entry Fee

Exploring the Magnificent Mile itself is completely free! 

Key attractions of Magnificent Mile

Chicago’s Magnificent Mile pulsates with iconic landmarks, world-class fashion, and enough dazzling experiences to fill your Windy City adventure. Prepare for key attractions:

  • Luxury heaven: Indulge in iconic brands like Cartier, Chanel, and Prada lining the prestigious Michigan Avenue.
  • Architectural marvels: Snap pics of the neo-Gothic Tribune Tower and the terracotta-clad Wrigley Building.
  • Unique finds: Explore boutiques and flagship stores for one-of-a-kind souvenirs and local designs.
  • Masterpiece magnet: Dive into the Art Institute of Chicago, housing Van Gogh’s “Starry Night” and countless other treasures.
  • Modern muse: Wander through the Museum of Contemporary Art Chicago, showcasing innovative exhibits and installations.
  • Performance passion: Catch a world-class show at the historic Chicago Theatre, hosting Broadway hits and renowned artists.
  • Michelin magic: Savor award-winning cuisine at restaurants like Roister or Alinea, pushing culinary boundaries.
  • Deep-dish dream: Dive into Chicago’s iconic deep-dish pizza at Gino’s East or Lou Malnati’s.
  • Global flavors: Embark on a culinary adventure with diverse options, from Ethiopian cuisine to trendy sushi spots.
  • Sky-high thrills: Soar 1,033 feet above the city with breathtaking views at 360 Chicago.
  • River cruise charm: Take a scenic cruise along the Chicago River for a unique perspective of the city skyline.
  • Holiday magic: Witness the dazzling Magnificent Mile Lights Festival, transforming the avenue into a winter wonderland.

4. Skydeck Chicago—Willis Tower

Willis Tower Chicago's Top Tourist Landmarks
Willis Tower, Chicago

Towering over the Windy City, Willis Tower (formerly Sears Tower) isn’t just Chicago’s Top Tourist landmark—it’s a skyscraper legend! ️


233 S Wacker Dr, Chicago, IL 60606, USA. You can easily reach it using public transportation or taxis.

Overview of Willis Tower

This architectural marvel is 110 stories tall and boasts breathtaking 360° views spanning four states. Daredevils, step out onto the iconic Ledge, with glass boxes jutting 4 feet out on the 103rd floor! (Not for the faint of heart!) New in 2022: Catalog, an immersive art experience showcasing Chicago’s vibrant neighborhoods.

Entry Fee

  • General admission costs $32 for adults and $26 for kids (3–11 years old).
  • The Ledge experience adds $19-$25 to your ticket.

Key attractions of Willis Tower

Look no further than Willis Tower, one of Chicago’s top tourist landmarks and an architectural masterpiece that promises an unforgettable experience. Ready to:

  • Soar to new heights: Ascend 1,033 feet to the Skydeck, the highest public observation deck in the US, offering breathtaking views spanning four states.
  • Step out into the void: Challenge your courage on The Ledge, with glass balconies extending four feet from the building, perfect for capturing vertigo-inducing selfies.
  • Explore interactive exhibits: Learn about the tower’s fascinating history and engineering marvels through engaging displays and multimedia experiences.
  • Dine with a view: Savor a delicious meal at The Skydeck Cafe, featuring panoramic vistas and a menu highlighting local flavors.
  • Catch a sunset spectacle: Witness the city bathed in golden light during a magical sunset experience on the Skydeck.

5. 360 Chicago Observation Deck

360 Chicago Observation Deck
360 Chicago Observation Deck

Ready to experience Chicago’s iconic skyline like never before? 360 Chicago, atop the Magnificent Mile, offers panoramic views and a unique thrill you won’t find at other of Chicago’s top tourist landmarks!


875 N Michigan Ave, Chicago, IL 60611

Overview of 360 Chicago Observation Deck

360 Chicago Observation Deck Unparalleled views from 1,000 feet up, stretching across four states. See iconic landmarks like Millennium Park and the Navy Pier in stunning detail from the 360 Chicago Observation Deck. TILT, a moving glass platform, will have you leaning out into the open air—not for the faint of heart. New interactive exhibits showcase Chicago’s diverse neighborhoods.

Entry Fee

  • General Admission starts at $30 for adults and $20 for kids (3-11 years).
  • TILT experience adds $16-$20.

Key attractions of 360 Chicago Observation Deck

Look beyond ordinary observation decks and ascend to the 94th floor of the iconic John Hancock Center, home to the 360 Chicago Observation Deck. Buckle up for an experience that’s:

  • Panoramic Perfection: Witness breathtaking 360° views stretching across the cityscape, encompassing Lake Michigan’s glistening blue expanse and iconic landmarks like Millennium Park and Navy Pier.
  • Thrill Seeker’s Paradise: Don’t miss TILT, a moving glass balcony tilting you outward 1,000 feet above the Magnificent Mile – get ready for unforgettable chills and Instagram-worthy snaps!
  • Interactive Journey: Immerse yourself in the interactive exhibits showcasing Chicago’s vibrant history and diverse neighborhoods, fueling your exploration beyond the skyline.
  • CloudBar Chill: Unwind at CloudBar, the highest bar in the city, and sip on handcrafted cocktails while soaking in the breathtaking panorama.
  • Special Events: Elevate your visit with unique experiences like 360 Sky Yoga, offering mindful practice with stunning backdrops, or seasonal events like the festive holiday light show.

6. Chicago Riverwalk

Chicago Riverwalk
Chicago Riverwalk

Forget museums (for a bit!), unwind and explore one of Chicago’s top FREE delights: the Chicago Riverwalk! ️


The south bank of the Chicago River stretches 1.25 miles from Lake Michigan to Lake Street.

Overview of Chicago Riverwalk

The Chicago Riverwalk, a 1.25-mile scenic path snaking along the south bank of the Chicago River, is more than just a walkway. It’s a vibrant tapestry woven with stunning architecture, delectable bites, exciting activities, and breathtaking natural beauty, offering a unique perspective of the Windy City’s soul.

Entry Fee

FREE to access! Just bring your walking shoes, camera, and sense of adventure.

Key attractions of Chicago Riverwalk

Dive into the Chicago Riverwalk, a hidden gem offering unique experiences and breathtaking views. Here’s a taste:

  • Urban Oasis: Wander along a scenic path lined with lush greenery, public art installations, and interactive fountains, offering a welcome escape from the city bustle.
  • Waterfront Delights: Rent a kayak or join a cruise to explore the city from a unique perspective, gliding under iconic bridges and admiring the magnificent architecture.
  • Foodie Paradise: Savor delicious meals al fresco on charming patios overlooking the river, offering everything from casual bites to upscale dining with stunning backdrops.
  • Festival Fun: Join in the vibrant energy of year-round events, from summer concerts and art fairs to festive holiday light displays, transforming the Riverwalk into a lively hub.
  • Hidden Gems: Seek out secret spots like the hidden gardens under bridges or the stunning Riverwalk Playhouse, which hosts intimate performances and cultural events.

7. Navy Pier

Navy Pier Chicago's Top Tourist Landmarks
Navy Pier, Chicago

Craving lakefront chills, dazzling cityscapes, & endless fun?  Set sail for Chicago’s iconic Navy Pier!


600 E Grand Ave, Chicago, IL 60611, USA.

Overview of Navy Pier

Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan, located in the Streeterville neighborhood of the Near North Side community area in Chicago, Illinois, United States. It is one of the most popular tourist destinations in the city, attracting over 9 million visitors each year. The pier was originally built in 1916 as a shipping and recreation facility. However, it fell into decline in the mid-20th century. In the 1980s, the city began a major redevelopment project, and the pier reopened in 1995 as a mixed-use entertainment complex.

Entry Fee

FREE to access! Just bring your walking shoes, camera, and sense of adventure.

Key attractions of Navy Pier

Here are the key attractions of the iconic Navy Pier:

  • Iconic Ferris Wheel: Take a spin on the iconic Navy Pier Ferris Wheel, offering stunning views of the city skyline and Lake Michigan.
  • Entertainment Galore: Enjoy a variety of entertainment options, including the Chicago Shakespeare Theater, live music performances, and outdoor movies.
  • Family Fun: Engage in family-friendly activities such as the Navy Pier Park, featuring rides, mini-golf, and the whimsical Children’s Museum.
  • Waterfront Exploration: Stroll along the picturesque waterfront, explore the scenic gardens, and embark on boat tours to discover the beauty of Chicago’s skyline from the water.
  • Year-Round Events: Experience the excitement of year-round events, including seasonal festivals, fireworks displays, and cultural celebrations, ensuring there’s always something new to discover at Navy Pier.

8. Wrigley Field

Wrigley Field - Chicago's Top Tourist Landmarks
Wrigley Field, Chicago

Baseball fans, rejoice! Today, we’re going to the iconic Wrigley Field, home of the Chicago Cubs. Whether you’re a die-hard Cubs supporter or a baseball enthusiast, Wrigley Field offers an unforgettable experience.


Wrigley Field is located in the heart of Chicago’s North Side, at 1060 W Addison St, Chicago, IL 60613.

Overview of Wrigley Field

Step back in time and soak up the atmosphere of one of baseball’s most iconic stadiums. Wrigley Field, nicknamed “The Friendly Confines,” has been the home of the Chicago Cubs since 1916. With its ivy-clad outfield walls, hand-operated scoreboard, and unique bleachers, it offers an unparalleled baseball experience. Wrigley Field is the second-oldest Major League Baseball stadium in the United States, after Fenway Park in Boston. It was designated a National Historic Landmark in 2020. The stadium is known for its friendly atmosphere and its die-hard Cubs fans.

Entry Fee

Tickets can range from around $50 for bleacher seats to over $500 for premium seating behind home plate.

Key attractions of Wrigley Field

Chicago’s iconic Wrigley Field, where baseball is more than just a game, it’s an experience! Here’s why you shouldn’t just dream of catching a fly ball but book your tickets now:

  • Ivy-clad magic: Witness the iconic green walls, a Major League Baseball rarity, and feel the electric atmosphere, especially during Cubs games.
  • Rooftop revelry: Snag a ticket to a rooftop bleacher for panoramic views, lively crowds, and a unique perspective on the game (or just the Chicago skyline!). ️
  • History comes alive: Take a stadium tour to explore hidden nooks, learn about legendary moments, and even peek into the press box.
  • Beyond baseball: Enjoy free movie nights, concerts, and fitness classes on Gallagher Way Plaza, or grab a bite at trendy nearby restaurants.
  • Winter wonderland: Don’t miss the Christkindlmarket during the holidays for festive cheer, unique gifts, and delicious treats.

9. Art Institute of Chicago

Art Institute of Chicago
Art Institute of Chicago

Journey through centuries of art at this iconic museum, boasting 300,000+ works from across the globe.


111 S Michigan Ave, Chicago, IL 60603

Overview of Art Institute of Chicago

Founded in 1879, the Art Institute of Chicago is one of the world’s oldest and largest art museums. Its collection spans over 5,000 years of art history, encompassing over 300,000 works of art from across the globe.

Entry Fee 

  • Adults: $32
  • Seniors (65+): $26
  • Students (college/university with ID): $26
  • Teens (14-17): $26
  • Children (under 13): Free

Key attractions of the Art Institute of Chicago

Forget the tourist traps, art lovers!  The Art Institute offers an immersive journey across continents and centuries, all under one magnificent roof. Here’s a taste of what awaits:

  • Iconic masterpieces: Gaze upon Van Gogh’s swirling “Bedroom,” Hopper’s hauntingly familiar “Nighthawks,” and Monet’s serene “Water Lilies.” ️
  • Global treasures: Explore ancient Egyptian sarcophagi, marvel at Japanese woodblock prints, and get lost in the vibrant hues of Islamic art.
  • Modern marvels: Witness contemporary masterpieces like Alma Thomas’s “Starry Night and the Astronauts,” pushing the boundaries of artistic expression.
  • Special exhibitions: Catch the ongoing “Picasso: Drawing from Life” to see the master’s intimate sketches, or delve into “Canova: Sketching in Clay” for a sculptor’s perspective. 
  • More than just art: Relax in the stunning Ryerson & Burnham Libraries, indulge in a gourmet lunch at the museum cafe, or browse unique gifts in the museum shop. 

10. Museum of Science and Industry

Museum of Science and Industry
Museum of Science and Industry

Have you ever dreamt of stepping into a real-life submarine, piloting a Boeing 727, or even exploring the depths of a coal mine? Well, at the Museum of Science and Industry in Chicago, you can do all that and more!


The Museum of Science and Industry, Chicago, is at 5700 S DuSable Lk Shr Dr, Chicago, IL 60637, USA.

Overview of the Museum of Science and Industry

The Museum of Science and Industry in Chicago is a renowned institution featuring interactive exhibits on science, technology, and industry. It offers immersive experiences, including a U-505 submarine tour and a recreated coal mine. The museum continues to engage visitors with new displays and educational programs, highlighting advancements in STEM fields.

Entry Fee 

  • Adult (ages 12 and up): $18
  • Child (ages 3-11): $14
  • Member (all ages): $9 (Annual Fund: FREE)

Key attractions of the Museum of Science and Industry

Unleash your inner scientist at the Museum of Science and Industry in Chicago. Uncover mind-blowing exhibits and iconic displays—we’re talking:

  • The actual Apollo 8 spacecraft: Blast off and walk beneath this lunar legend.
  • Colleen, the world’s largest steam locomotive: See this behemoth up close and feel the power of innovation.
  • Science Storms: Ride a simulated tornado, create lightning, and defy gravity—all in one place.
  • Fab Lab: Get hands-on and invent something awesome using laser cutters, 3D printers, and more.
  • Featured exhibit: Future Energy Chicago: Explore new solutions for a sustainable tomorrow.

Tips for visiting Chicago’s Top Tourist Landmarks

Ready to feel the thrill of travel in Chicago? Book your luxurious vacation rental and experience the city in comfort and style. This guide offers insider tips to maximize your Windy City experience.

Here are the tips:

  • Public Transportation: Utilize the efficient “L” trains and buses.
  • Weather Preparedness: Chicago experiences varying weather; bring layers.
  • Exploring Neighborhoods: Venture beyond downtown for diverse cultural experiences.
  • Dining Diversity: Indulge in Chicago’s renowned food scene, from deep-dish pizza to Michelin-starred restaurants.
  • Safety Awareness: Stay alert in tourist areas and be mindful of your surroundings.
  • City Passes: Consider purchasing a Chicago CityPASS for discounted access to top attractions.
  • Events Calendar: For added excitement, check for festivals and events during your visit.
  • Lakefront Activities: Enjoy parks, beaches, and recreational opportunities along Lake Michigan.


In wrapping up our exploration of Chicago’s Top 10 Tourist Landmarks, it’s evident that this city holds a treasure trove of iconic sites waiting to be uncovered. From the historic Navy Pier to the picturesque views atop the John Hancock Center, each landmark offers a glimpse into the vibrant essence of Chicago. 

As we conclude our journey, let’s remember to cherish the memories created amidst these architectural wonders. Now, it’s your turn to embark on your adventure through Chicago’s top tourist landmarks. So pack your bags, gather your companions, and set forth to create unforgettable experiences. 

Have a safe trip, and may your journey be filled with joy and discovery!


Q1. What are the best times to visit Chicago for sightseeing?

Fall (Sept-Oct) or spring (April-May) offers mild weather, fewer crowds, & sightseeing deals. Consider your interests for specifics.

Q2. Where can I stay near Chicago’s top tourist landmarks?

Consider the Loop/Millennium Park area for the Cloud Gate & Art Institute, Magnificent Mile for shopping & museums, or River North for nightlife and the Navy Pier.

Q3. What if I have limited time to visit Chicago?

If you have limited time to visit Chicago, prioritize Millennium Park, Navy Pier, and Willis Tower.

Q4. What’s the best way to get around Chicago?

The best way to get around is through public transportation (CTA), which is convenient and affordable.

Q5. Where can I find more information about Chicago?

You can find more information about Chicago.