Chicago, the Windy City, is a place brimming with culture, history, and iconic landmarks. Whether you’re visiting for a weekend or a longer stay, there is no shortage of activities that will make your trip unforgettable. From scenic lakefront views to deep-dish pizza indulgence, Chicago has something for everyone.

Here’s your ultimate guide to the best things to do in Chicago.

Navy Pier

Start your Chicago adventure at one of its most famous attractions: Navy Pier. Stretching out over Lake Michigan, this iconic pier offers a variety of activities. Ride the Centennial Wheel for panoramic views of the city skyline, visit the Chicago Children’s Museum. Navy Pier also features numerous dining options, shops, and often hosts festivals and live performances. It’s a perfect spot for a day of entertainment and exploration.

Chicago Architecture Boat Tour

One of the best ways to appreciate Chicago’s architectural marvels is from the water. The Chicago Architecture Boat Tour takes you along the Chicago River, where you can admire the city’s skyline, learn about its history, and get a closer look at the famous buildings that define the city. 

Chicago’s architectural story begins with a pivotal event: The Great Chicago Fire of 1871. This devastating blaze, which destroyed much of the city, forced architects and urban planners to rethink how buildings should be constructed. With most of the city in ruins, Chicago had an opportunity to rebuild with new materials and techniques that would ultimately reshape the city’s skyline.

As you embark on the boat tour, your knowledgeable guide will take you on a journey through this architectural revolution, pointing out famous landmarks. It’s an unforgettable way to see the city from a new perspective while learning about the forces that shaped its stunning skyline.

Millennium Park & The Bean

A visit to Millennium Park is a must when in Chicago. This urban park is home to the famous Cloud Gate sculpture (also known as “The Bean”). The shiny, reflective surface of the Bean creates a unique photographic opportunity, especially as it reflects the city skyline. 

Located in the heart of the city, Millennium Park is an 24.5-acre urban park offers a perfect blend of art, architecture, and green space. The park is home to a variety of attractions, but none more iconic than Cloud Gate, the sculpture commonly known as The Bean. The sculpture was designed by British artist Anish Kapoor, and its development was funded as part of a larger effort to revitalize Chicago’s downtown area. The Bean is a perfect example of how Chicago has long been at the forefront of architectural and artistic innovation. Cloud Gate’s reflective surface offers a stunning way to engage with the city’s architecture, as it mirrors the surrounding skyline, distorting and transforming iconic buildings.

Whether you’re visiting Millennium Park for the first time or revisiting an old favorite, the Bean remains one of Chicago’s most beloved and enduring landmarks. While you’re in the park, check out the Jay Pritzker Pavilion, a stunning outdoor concert venue, or enjoy the Lurie Garden, a peaceful oasis in the heart of the city.

Art Institute of Chicago

The Art Institute of Chicago is one of the world’s premier art museums and a must-see for culture lovers. Located just a short walk from Millennium Park, the museum boasts an impressive collection of works from renowned artists. If you only have time for one attraction in Chicago, I highly recommend visiting this iconic museum.

Chicago Museums

Chicago is a city rich in culture and history, and its museums are a testament to that legacy. Whether you’re an art enthusiast, history buff, or science lover, Chicago offers world-class institutions that provide engaging, educational, and awe-inspiring experiences for visitors of all ages. Many of these museums are located in Grant Park and the nearby Museum Campus, a designated cultural area along Lake Michigan, which has long been a hub for Chicago’s civic and cultural development.

Here’s a closer look at some of the city’s top museums and their historical significance:

Field Museum

Located along the picturesque lakefront, the Field Museum is one of Chicago’s most iconic institutions. Founded in 1893 for the World’s Columbian Exposition, the museum’s vast collection covers everything from ancient civilizations to the natural world. One of its most famous exhibits is Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered. Explore exhibits on ancient civilizations, gems and minerals, and the natural world. It’s an educational and awe-inspiring experience for all ages.

Shedd Aquarium

The Shedd Aquarium is another landmark of the Museum Campus, offering one of the most impressive aquatic experiences in the world. With exhibits that include everything from colorful coral reefs to beluga whales and sea otters, the aquarium offers an up-close look at aquatic animals from around the globe.

Museum of Science and Industry

The Museum of Science and Industry is one of the largest science museums in the world. It’s packed with interactive exhibits, including a U-505 submarine (the only German submarine in the U.S.), the Science Storms exhibit, and a fascinating display of the history of flight. The museum is ideal for both kids and adults.

Adler Planetarium

Located on the shores of Lake Michigan, the Adler Planetarium offers a stellar experience with interactive exhibits about space, the universe, and our place within it. The planetarium also features immersive sky shows that allow you to explore distant galaxies, planets, and stars.

Chicago Views

Chicago’s skyline is one of the most recognizable in the world, and there are several great spots to take in the views.

Skydeck Chicago

The Skydeck at the Willis Tower (formerly the Sears Tower) offers one of the best views in the city. Take an elevator ride up to the 103rd floor, where you can step out onto The Ledge, a glass-enclosed balcony that extends outside the building. The views of Chicago and Lake Michigan are breathtaking, especially at sunset.

360 Chicago

For another unforgettable view of Chicago, head to the 360 Chicago Observation Deck on the 94th floor of the John Hancock Center. This observation deck offers a 360-degree view of the city, and for an extra thrill, try the TILTexperience, which tilts you outward over the city for a heart-racing experience.

If you have to decide between Skydeck at Willis Tower and 360 Chicago, it ultimately comes down to the kind of experience you’re looking for. Both offer spectacular views, so it depends on whether you prefer the extra thrill or the iconic experience. Choose 360 Chicago’s TILT experience if you enjoy an adrenaline rush and Skydeck for an iconic Chicago experience with  incredible view.

Chicago Waterfronts

When visiting Chicago, exploring its waterfronts is a must, but whether you choose the Lakefront or the Riverwalk depends on the type of experience you’re looking for. Each offers a distinct way to enjoy the city’s natural beauty and vibrant atmosphere.

Chicago Lakefront

The Chicago Lakefront is perfect for those seeking tranquility and outdoor activities by the water. Stretching along Lake Michigan, it provides expansive views, peaceful beaches, and scenic walking and biking paths. The Lakefront Trail, which spans over 18 miles, is perfect for cyclists, joggers, and anyone looking to take a leisurely stroll while enjoying beautiful lake views. You can also explore the area on a guided Segway tour.

Chicago Riverwalk

On the other hand, the Chicago Riverwalk offers a lively and urban experience right in the heart of the city. Running along the Chicago River, the Riverwalk is a hub for dining, shopping, and cultural exploration. It’s lined with vibrant restaurants, cafes, and bars, making it a fantastic spot for lunch or a drink with a view of the city’s stunning architecture.

Grant Park

Make your way to Grant Park, often referred to as “Chicago’s front yard,” where you’ll find the beautiful Buckingham Fountain. The fountain is one of the largest in the world, and it puts on a spectacular light and water show in the evenings during the warmer months.

Chicago Theater

The historic Chicago Theater is a stunning venue for live performances, from Broadway shows to concerts and comedy acts. The marquee outside is iconic, and if you’re a theater buff, be sure to check out their schedule. Even if you’re not catching a show, the building itself is worth admiring for its opulent architecture.

Chicago Chinatown

Explore the vibrant heart of Chicago’s Chinatown, located just south of the Loop. This dynamic neighborhood offers a rich cultural experience with its blend of traditional and modern elements, from delicious restaurants to unique shops and cultural landmarks. One of the standout features is the Chinatown Gate, a stunning symbol of the community’s heritage, and the Chinese-American Museum of Chicago, which highlights the history and contributions of Chinese immigrants.

Another must-see is the Nine Dragon Wall, a stunning replica of the famous wall found in Beijing’s Beihai Park. This intricate wall, adorned with nine colorful, hand-crafted dragons, is not only a work of art but also a symbol of prosperity and protection for the neighborhood. The Nine Dragon Wall  is one of the only three such replicas outside of China making it rare and significant feature in Chicago Chinatown. 

For a relaxing retreat, head to Ping Tom Memorial Park, a peaceful green space that sits along the Chicago River. The park features beautiful gardens, a pond, and a traditional Chinese-style pavilion, making it an ideal spot to relax and enjoy the surroundings. It also offers stunning views of the city’s skyline and is a great place to unwind after exploring the neighborhood.

While you’re in the area, be sure to sample authentic Chinese food at local eateries. Chicago’s Chinatown offers a truly immersive experience that connects visitors to both the past and present of Chinese-American culture.

Try Deep-Dish Pizza & Hot Dogs

No trip to Chicago is complete without sampling the city’s iconic dishes.

Chicago is famous for its thick, cheesy, and hearty Deep-Dish Pizza. A must-try is Lou Malnati’s. Be sure to order it Chicago-style, with a buttery crust, mozzarella, tomato sauce, and all your favorite toppings.

A true Chicago Hot Dog is an art form. A classic comes with a poppy seed bun, mustard, onions, relish, tomato slices, peppers, and a pickle—no ketchup! You’ll find some of the best hot dogs at Portillo’s.

What is the Best Time to Visit Chicago?

Chicago is a vibrant city with something to offer year-round, but the best time to visit depends on what kind of experience you’re seeking. Here’s a breakdown of the best times to visit Chicago, depending on your interests.

• Winter (December to February): Holiday festivities, winter sports, and fewer tourists, but cold temperatures.
• Spring (April to June): Great weather, fewer crowds, outdoor festivals and some unique events.
• Summer (June to August): Warm weather, outdoor activities, and major festivals, but expect larger crowds.
• Fall (September to November): Mild temperatures, beautiful foliage, and a mix of outdoor and indoor activities.

Should you buy Chicago CityPASS ?

The Chicago CityPASS grants you access to five of the city’s top attractions, making it an ideal option for first-time visitors or those looking to explore the major sights. The CityPASS is valid for 9 consecutive days, starting from the date of your first use. The pass offers a great opportunity to save money if you plan on visiting most or all of the included attractions and are okay with the set options. Here’s what’s included:

Included Attractions:

1. Shedd Aquarium
2. Skydeck Chicago (Willis Tower)

Plus, you can choose any three from the following list:

• Shoreline Sightseeing Architecture River Tour (Weather dependent)
• Field Museum
• 360 CHICAGO Observation Deck (John Hancock Center)
• Museum of Science and Industry
• Art Institute of Chicago
• Adler Planetarium

When Should You Buy CityPASS?

CityPASS is a great deal if you intend to see several of the top attractions and can commit to visiting the specific sites listed. It’s especially worthwhile for those who are short on time and want to maximize their sightseeing.

When to Skip the CityPASS?

If you’re only interested in one or two of the attractions, or if you don’t plan to visit all the attractions within the 9-day window, it might be more cost-effective to purchase individual tickets instead.

Chicago is a city that blends history, culture, and modernity in the most exciting ways. Whether you’re cruising down the river on an architecture tour, exploring world-class museums, or indulging in deep-dish pizza, there’s no shortage of things to do and see. So pack your bags and get ready for an adventure in one of America’s most vibrant cities!

Don’t forget to pin this Chicago Guide to your Pinterest board for easy access while planning your trip! It’s the perfect reference to keep all your must-see spots and local tips in one place.