Things to do in Chicago

Discover the top attractions, dining spots, and entertainment options with our comprehensive guide to the best things to do in Chicago.

12/26/20238 min read

Chicago, the bustling metropolis situated on the shores of Lake Michigan, offers a multitude of exciting experiences for both locals and visitors alike. From its architectural wonders to its renowned food scene, this city truly has it all. So, if you're wondering what to do in the Windy City, look no further. We've compiled a comprehensive guide to the best attractions, landmarks, cultural hotspots, dining spots, shopping destinations, and nightlife options that will ensure an unforgettable trip to Chicago.

Chicago, often referred to as the "Windy City," is a vibrant metropolis that offers a plethora of exciting activities and attractions for visitors to enjoy. From exploring its unique charm to immersing yourself in its rich history and culture, there is something for everyone in this bustling city. Let's dive into the top things to do in Chicago.

Exploring the Windy City: An Overview

Chicago is known for its distinct character and vibrant energy. As soon as you step foot in this city, you'll be captivated by its stunning architecture, world-class museums, and thriving arts scene. The unique blend of history and modernity makes Chicago a fascinating destination that never fails to leave a lasting impression.

But what truly sets Chicago apart is its unique charm. The city's iconic skyline, dominated by architectural marvels like the Willis Tower and the John Hancock Center, creates a jaw-dropping backdrop for your adventures. As you wander through the bustling streets, you'll find yourself surrounded by a vibrant mix of old and new, where historic buildings stand side by side with sleek skyscrapers.

One of the best ways to experience the charm of Chicago is by exploring its diverse neighborhoods. The Loop, with its bustling business district, is home to iconic landmarks like Millennium Park and Grant Park. Take a leisurely stroll along the Chicago Riverwalk and admire the stunning views of the city's skyline reflected in the water.

River North, known for its vibrant art scene, is a must-visit for art enthusiasts. Explore the numerous galleries and art studios that line the streets, showcasing a wide range of artistic styles and mediums. Indulge in the culinary delights of this neighborhood, with its plethora of trendy restaurants and chic cafes.

The Magnificent Mile, a stretch of Michigan Avenue, is a shopper's paradise. This world-renowned shopping district is home to luxury boutiques, department stores, and flagship stores of top fashion brands. Whether you're looking for high-end fashion, unique souvenirs, or the latest gadgets, you'll find it all on the Magnificent Mile.

The Rich History of Chicago

Chicago's charm is not only found in its architecture and neighborhoods but also in its rich history. The city has played a significant role in shaping the United States, from its early days as a trading post to its rise as a major industrial and cultural hub.

Step back in time and explore the historic sites that tell the story of Chicago's past. Visit the Chicago History Museum, where you can delve into the city's history through interactive exhibits and artifacts. Take a walk through the Prairie Avenue Historic District, home to some of the city's most beautiful mansions from the late 19th and early 20th centuries.

For a taste of Chicago's architectural heritage, take a guided tour of the Frank Lloyd Wright Home and Studio in nearby Oak Park. This iconic building showcases the early work of one of America's most renowned architects.

Chicago is also known for its role in the Prohibition era, when speakeasies and gangsters ruled the streets. Explore the hidden world of Chicago's underground bars and secret tunnels on a Prohibition-themed tour, where you'll learn about the city's notorious past.

As you explore Chicago's rich history, you'll gain a deeper appreciation for the city's unique character and the stories that have shaped it into the vibrant metropolis it is today.

Must-Visit Landmarks in Chicago

Architectural Marvels in the City

Chicago is a haven for architecture enthusiasts. Take a stroll along the Chicago Riverwalk and admire the unique blend of modern and historic buildings. Marvel at the towering skyscrapers that line the river, showcasing the city's impressive skyline. As you walk, you'll notice the intricate details and innovative designs that make Chicago's architecture truly remarkable.

Make sure to visit the breathtaking Millennium Park, a sprawling green space in the heart of the city. Here, you'll find the famous Cloud Gate sculpture, known affectionately as "The Bean." This iconic stainless steel structure reflects the city's skyline and provides a unique perspective for visitors. Take a moment to capture a selfie or simply sit and admire the surrounding beauty.

Don't miss the opportunity to embark on an architectural boat tour along the Chicago River. As you cruise along the water, you'll learn about the city's fascinating history and architectural heritage from expert guides. Marvel at the diverse range of architectural styles, from Gothic revival to modernist masterpieces. Gain a deeper understanding of how Chicago's skyline has evolved over time and appreciate the vision and skill of the architects who shaped the city.

Historical Sites Worth Your Time

To truly appreciate Chicago's rich history, make your way to the Chicago Cultural Center. This stunning landmark, housed in a historic building, is a hub for arts and culture. Explore the grand halls and marvel at the intricate mosaics, stunning stained glass windows, and ornate ceilings. The center hosts a range of art exhibitions, live performances, and cultural events, offering a glimpse into the vibrant arts scene of the city.

Continue your historical journey by visiting the iconic Navy Pier. This historic site, originally built as a shipping and recreation facility, has transformed into a popular tourist destination. As you stroll along the pier, take in the breathtaking views of Lake Michigan. Enjoy the lively atmosphere and explore the various entertainment options and attractions, including amusement rides, restaurants, and shops. Learn about the pier's fascinating history and its role in the city's development.

Immerse yourself in the stories of Chicago's past by visiting the Chicago History Museum. Located in the Lincoln Park neighborhood, this museum offers a comprehensive look at the city's history, from its early days as a trading post to its rise as a major metropolis. Explore the exhibits that showcase the city's diverse cultural heritage, significant events, and influential figures. Gain a deeper understanding of the city's past and how it has shaped its present.

Chicago's Vibrant Arts and Culture Scene

Chicago is a city known for its vibrant arts and culture scene, offering a plethora of experiences for visitors to explore. From world-class museums and art galleries to music and theater experiences, there is something for everyone to enjoy.

Top Museums and Art Galleries

Step into the world of art and culture by visiting the renowned Art Institute of Chicago. Located in Grant Park, the Art Institute is home to an extensive collection of masterpieces from around the world. Marvel at iconic works such as Grant Wood's "American Gothic" and Vincent van Gogh's "The Bedroom." The museum also features rotating exhibitions that showcase a diverse range of artistic styles and periods.

For those interested in contemporary art, the Museum of Contemporary Art is a must-visit destination. Located in the heart of downtown Chicago, this museum is a hub for cutting-edge exhibitions and immersive experiences. Explore thought-provoking installations and engage with contemporary artists pushing the boundaries of artistic expression.

Delve into Chicago's African American history and culture at the DuSable Museum of African American History. Located in the historic Hyde Park neighborhood, this museum offers a comprehensive look at the contributions and experiences of African Americans throughout history. Discover exhibits highlighting the achievements of notable figures like Barack Obama and explore the rich cultural heritage of the African American community.

Music and Theater Experiences

Chicago is a city that loves music and theater, with a thriving performing arts scene that attracts both locals and tourists alike. The Loop, Chicago's downtown district, is home to many world-class theaters where you can catch Broadway shows and other theatrical performances. From classic musicals to thought-provoking dramas, there is always a show to suit every taste.

Immerse yourself in Chicago's rich jazz heritage by visiting iconic venues like the Green Mill Cocktail Lounge. Located in the Uptown neighborhood, the Green Mill has been a staple of the city's jazz scene since the 1900s. Enjoy live performances by talented musicians while sipping on a classic cocktail in this historic setting.

Don't miss the opportunity to explore Chicago's Blues Trail, a musical journey that takes you through the city's rich blues history. From legendary clubs like Buddy Guy's Legends to hidden gems tucked away in neighborhood corners, you'll find yourself surrounded by the soulful sounds of the blues. Experience live performances by local musicians and feel the rhythm that has shaped Chicago's musical landscape.

Whether you're a lover of visual arts, theater, or music, Chicago's arts and culture scene offers a diverse range of experiences that will leave you inspired and entertained. Soak in the creativity and talent that permeates the city, and discover why Chicago is a destination beloved by art enthusiasts from around the world.

Outdoor Activities in Chicago

Parks and Recreation Areas

Escape the hustle and bustle of the city by visiting Chicago's beautiful parks and recreation areas. Millennium Park, with its stunning architecture and outdoor art installations, offers a serene oasis in the heart of the city. For nature lovers, Grant Park is a must-visit, with its expansive green spaces and breathtaking views of Lake Michigan.

Water-Based Adventures

With its prime location on the shores of Lake Michigan, Chicago boasts an array of water-based activities. Take a boat tour along the Chicago River and enjoy the city's stunning skyline from a different perspective. For a more adventurous experience, try kayaking or paddleboarding on Lake Michigan's crystal-clear waters.

Food and Drink Experiences in Chicago

Iconic Chicago Dishes to Try

No visit to Chicago is complete without indulging in its iconic dishes. Treat yourself to a classic Chicago-style deep-dish pizza or savor the city's famous Chicago-style hot dogs. Don't forget to try the mouthwatering Italian beef sandwich, a local favorite.

Best Local Breweries and Wineries

For beer and wine enthusiasts, Chicago offers a thriving craft beer scene and a variety of wineries to explore. Visit popular breweries like Revolution Brewing or Half Acre Beer Company to sample a wide range of unique and delicious brews. Wine lovers can embark on a tasting journey at Chicago's local wineries, such as City Winery or Lynfred Winery.

Shopping Destinations in Chicago

Famous Shopping Districts

Shopaholics will be in heaven when they visit Chicago. The Magnificent Mile, a bustling stretch of Michigan Avenue, is home to a plethora of luxury boutiques, department stores, and specialty shops. For a more unique shopping experience, head to neighborhoods like Wicker Park and Andersonville, where you'll find an array of local boutiques with one-of-a-kind treasures.

Unique Local Boutiques

If you're looking for unique, locally made souvenirs, be sure to explore the independent boutiques scattered throughout the city. From handmade jewelry to custom clothing, these boutiques offer a chance to support local artisans and take home something truly special.


In conclusion, Chicago is a city that is brimming with incredible attractions and activities for visitors of all interests. From exploring its architectural wonders to immersing yourself in its vibrant arts and culture scene, this city offers a multitude of experiences that will leave you inspired and captivated. So, pack your bags and get ready to embark on an unforgettable journey in the Windy City!

Start planning your trip to Chicago today and discover why it is one of the most exciting destinations in the United States!