11 Must visit places in Chicago, Ultimate Guide

Chicago is a vibrant city packed with world-class attractions, iconic landmarks, and a rich cultural scene. Whether you’re a first-time visitor or a seasoned traveler, the Windy City offers something for everyone, from breathtaking skyline views and historic architecture to award-winning restaurants and legendary museums.

On a recent trip, we explored some of the best things to do in Chicago, and I’m excited to share some of the best must-visit attractions that should be on every traveler’s list. If you’re planning your first trip, this guide covers the classic Chicago experiences, from the Skydeck at Willis Tower to the deep-dish pizza joints that define the city’s food scene.

Of course, one trip isn’t enough to see it all, so consider this your ultimate Chicago bucket list, with plenty of reasons to return for more!

Iconic Landmarks & Attractions

1. The Willis Tower Skydeck

It stands 103 stories tall. The Willis Tower (formerly Sears Tower) is the tallest building in Chicago and a true architectural icon. From 1974 to 1998, it held the title of the tallest building in the world, and today, it remains one of the most visit places in the Chicago.

The Skydeck on the 103rd floor offers 360-degree panoramic views of Chicago’s skyline. The most thrilling feature? The Ledge is a series of glass-floored balconies. It extends from the buildings, which allow visitors to look straight down for an unforgettable view.

Visiting the Skydeck was on my Chicago bucket list, especially after seeing countless breathtaking photos of The Ledge. Upon arrival, we explored a small exhibit that shows the architectural history of Chicago, complete with detailed replicas of the most famous buildings of the city. Afterward, a high-speed elevator took us to the observation deck, where we spent about 20 minutes taking in the stunning views. If you’re to visit places in Chicago for the first time, this is an experience you won’t want to miss!

2. Millennium Park & Cloud Gate (“The Bean”)

Millennium Park is one of the most famous green spaces in Chicago. It offers a scenic escape between the city and Lake Michigan. At its heart stands Cloud Gate, better known as “The Bean”. It is a massive, mirror-like sculpture that reflects the skyline, lake, and visitors, which creates a dynamic and interactive experience.

As one of the busiest attractions in Chicago, Cloud Gate is almost always packed with tourists. To avoid the crowds, we arrived at sunrise, capturing stunning, unobstructed photos as the morning light transformed the reflective surface. Whether you’re exploring the park’s gardens, fountains, or public art installations, Millennium Park is a must-visit places on any Chicago itinerary.

3. Navy Pier

It was originally built in 1916 as a shipping and recreation hub. Navy Pier has since evolved into one of the top attractions of Chicago. This spans over 50 acres. It offers a mix of public spaces, restaurants, family-friendly activities, and community events. A highlight is the Centennial Wheel, a towering 200-foot Ferris wheel built to celebrate the pier’s 100th anniversary in 2016.

We combined our Navy Pier visit with a walk along the Chicago Riverwalk, taking in stunning views of the city skyline and Lake Michigan. Though we arrived in the morning, before the rides opened, we enjoyed the lively atmosphere and scenic waterfront. If I return to Chicago, I’d love to visit in the evening when the pier comes alive with fireworks and illuminated skyline views and is one of the best visit places in the Chicago.

Visitor Tip: Check the Navy Pier events calendar before your visit! From live performances to seasonal celebrations, there’s always something happening at this iconic Chicago landmark.

4. The Art Institute of Chicago

It is located near Millennium Park. The Art Institute of Chicago is one of the most renowned art museums in the world and visit places in the Chicago.. Home to an extensive collection of masterpieces, it features works by van Gogh, Warhol, Seurat, and countless others.

We initially planned to explore the entire museum but quickly realized its massive size would require an entire day. Instead, we used the museum map to navigate directly to the exhibits we were most excited about. Even in just under two hours, we were able to admire some of the most famous pieces in art history.

Visitor Tip: If you’re short on time, plan ahead by checking the highlights of museum online and mapping out your must-see exhibits.

5. The Chicago Riverwalk

It stretches 1.25 miles along the Chicago River. The Chicago Riverwalk offers a picturesque blend of architecture, waterfront views, and relaxation spots. This pedestrian-friendly path is lined with restaurants, seating areas, and scenic overlooks. This makes it the perfect place to take a stroll, grab a bite, or simply admire the skyline of a city.

Throughout our three-day trip, we found ourselves returning to the Riverwalk, both as a destination and as a convenient route between attractions. No Chicago itinerary is complete without experiencing this beautiful riverside promenade.

Visitor Tip: For a unique perspective of the city, consider taking a Chicago architecture boat tour from the Riverwalk. It’s one of the best ways to see the skyline!

Cultural & Historical Attractions

6. The Field Museum

Step into the Field Museum. It is one of the top natural history museums in the world, and must visit places in the Chicago. and come face-to-face with Titanosaur, the largest creature ever discovered. Another must-see is SUE the T. rex, the most complete and best-preserved Tyrannosaurus rex fossil ever found.

With exhibits spanning dinosaurs, ancient civilizations, and rare gems. The Field Museum offers an immersive experience for history and science lovers alike.

Visitor Tip: Plan at least a few hours to explore. There’s so much to see beyond the dinosaurs which includes mummies, meteorites, and cultural artifacts from around the world.

7. Museum of Science and Industry

It is located just outside downtown Chicago. The Museum of Science and Industry (MSI) is a must-visit for those who love interactive exhibits and groundbreaking discoveries. With over 20 rotating exhibits, there’s something for every curiosity. Space exploration, human anatomy, weather phenomena, and more.

Though I wasn’t sure what to expect, I was pleasantly surprised by how engaging and immersive the museum was. Even without a deep science background, I found myself fascinated by the exhibits and spent over 2.5 hours exploring the museum. The general admission fee of $25 grants access to most displays, but some special exhibits and experiences may require an additional fee.

Visitor Tip: Plan your visit beforehand and check which special exhibits are available. You might get to experience a submarine tour, a tornado simulation, or even a space shuttle replica!

8. Shedd Aquarium

The Shedd Aquarium is one of the must visit places in the Chicago. It offers visitors a chance to explore the wonders of the deep sea, freshwater ecosystems, and marine life from worldwide. The aquarium is home to 32,000+ aquatic animals, from vibrant coral reefs and Amazonian creatures to playful sea otters and beluga whales.

A highlight of the visit is the Oceanarium, where you can watch dolphins leap and sea lions glide through the water. The immersive exhibits make it a great experience for both kids and adults.

Visitor Tip: Arrive early to avoid long lines, and consider purchasing a CityPASS to save on admission if you plan to visit multiple Chicago attractions.

Best Outdoor & Scenic Spots

9. Lincoln Park & Lincoln Park Zoo

Lincoln Park is not just the largest park of Chicago. It’s also a vibrant neighborhood packed with culture and attractions. Whether you’re strolling through lush gardens, visiting historic landmarks, or admiring stunning Lake Michigan views, Lincoln Park offers something for everyone.

A highlight of the park is the Lincoln Park Zoo. It is one of the oldest and last remaining free zoos in the U.S.. Home to lions, gorillas, penguins, and more, it’s a perfect family-friendly destination. Nearby, the Lincoln Park Conservatory showcases exotic plants in a stunning glass greenhouse, while the Chicago History Museum dives deep into the fascinating past of a city.

Visitor Tip: Take a walk along the Lakefront Trail for some of the best skyline views in Chicago, especially at sunrise or sunset!

10. The 606 Trail

The 606 Trail is a 2.7-mile elevated pathway that was once an old railway line, now transformed into a scenic urban trail. Stretching through four vibrant neighborhoods, this multi-use trail is perfect for biking, jogging, or a leisurely walk while enjoying public art, gardens, and skyline views.

Lined with murals, sculptures, and green spaces, the 606 connects Wicker Park, Bucktown, Humboldt Park, and Logan Square, offering a unique way to experience Chicago’s culture and architecture. Whether you’re a fitness enthusiast or just looking for a peaceful escape from the city’s hustle, this trail is a must-visit.

Visitor Tip: Visit at sunset for a stunning view of the Chicago skyline, and stop by one of the many cafés and breweries along the way for a post-walk treat.

11. Grant Park & Buckingham Fountain

Grant Park, which is often called “Chicago’s Front Yard”. It is a sprawling 319-acre green space in the city’s heart. This is home to some of the most famous landmarks of Chicago. This includes the Art Institute of Chicago, Millennium Park, and Buckingham Fountain. The park also hosts major events like Lollapalooza and the Taste of Chicago food festival.

At the center of Grant Park sits the iconic Buckingham Fountain. It is one of the largest fountains in the world. Inspired by the fountains of Versailles, it features dazzling water displays every hour, shooting water up to 150 feet in the air, with a spectacular light and music show at night.

Visitor Tip: Visit in the evening to see the illuminated fountain show, and take a scenic walk along the Lakefront Trail for stunning skyline views.

Food & Dining Hotspots

Deep-Dish Pizza: A Chicago Classic

No trip to Chicago is complete without indulging in deep-dish pizza. With its buttery crust, layers of cheese, and chunky tomato sauce, it’s a must-try for food lovers. Two of the most famous spots to grab a slice are:

• Lou Malnati’s: This is known for its crispy, buttery crust and fresh mozzarella. Lou Malnati’s serves a classic deep-dish experience.
• Giordano’s: It is famous for stuffed deep-dish pizza. Giordano’s offers an extra cheesy, hearty bite.

Chicago-Style Hot Dogs: A Local Favorite

A true Chicago-style hot dog is an all-beef frank topped with mustard, onions, relish, tomato slices, sport peppers, a pickle spear, and celery salt. All on a poppy seed bun (never ketchup!). The best place to grab one?

• Portillo’s: A Chicago institution serving authentic Chicago dogs, Italian beef sandwiches, and crinkle-cut fries.

Best Cafés & Brunch Spots

Chicago has an incredible café and brunch scene which is perfect for starting your day. Some must-visit spots include:

• Wildberry Pancakes & Café: It is known for fluffy pancakes, stuffed French toast, and signature omelets.
• The Allis at Soho House: Stylish spot offering craft coffee, tea, and decadent pastries.
• Big Shoulders Coffee: A local favorite for high-quality, freshly roasted coffee.

Visitor Tip: For the best deep-dish pizza experience, be prepared for a wait. Order ahead or go at off-peak hours!

Best Neighborhoods to Explore

Chicago is a city of diverse neighborhoods, each with its own unique charm, history, and must-see attractions. Whether you’re drawn to iconic architecture, trendy boutiques, cultural enclaves, or vibrant nightlife, there’s a neighborhood for you. Here are three of the best areas to explore which I like:

1. The Loop – Chicago’s Iconic Downtown

The Loop is the heart of Chicago. It is where you’ll find skyscrapers, world-class museums, and historic landmarks. This is the perfect place for first-time visitors to experience the city’s energetic urban vibe.

Top Things to Do in The Loop:

Millennium Park & Cloud Gate (The Bean): Snap a selfie with Chicago’s most famous sculpture.
The Art Institute of Chicago: It is home to masterpieces by van Gogh, Monet, and Warhol.
Willis Tower Skydeck: Step onto The Ledge for a thrilling glass-floor view of the city.
Chicago Riverwalk: A scenic promenade lined with restaurants, bars, and breathtaking views.

Insider Tip: Catch a Broadway show at the Chicago Theatre or explore the historic Cultural Center for free art exhibits!

2. Wicker Park & Bucktown – Chicago’s Hipster Haven

If you love trendy cafés, boutique shopping, street art, and a buzzing nightlife, head to Wicker Park & Bucktown. These neighborhoods are known for their artsy, eclectic vibe and some of the best bars and restaurants in the city.

Top Things to Do in Wicker Park & Bucktown:

Shop along Milwaukee Avenue: Find indie boutiques, thrift stores, and record shops.
Sip craft coffee at The Wormhole Café: It is an 1980s-themed coffee shop with a DeLorean inside.
Explore the 606 Trail: A converted rail line turned into an elevated walking and biking path.
Enjoy rooftop drinks at The Robey: The chic hotel with stunning skyline views.

Insider Tip: Love live music? Check out Subterranean or The Empty Bottle, two of the best indie music venues of Chicago!

3. Chinatown – A Taste of Authentic Culture

Chicago’s Chinatown is one of the most vibrant and historic in the U.S. It offers authentic Chinese cuisine, traditional shops, and cultural landmarks. It’s a must-visit for foodies and those looking to experience a different side of Chicago.

Top Things to Do in Chinatown:

Try Dim Sum at MingHin Cuisine: The local favorite for steamed dumplings and BBQ pork buns.
Visit Ping Tom Memorial Park: It is a peaceful green space with river views and Chinese-style gardens.
Shop for souvenirs on Wentworth Avenue: Find tea shops, bakeries, and specialty stores.
Explore Chinatown Square: Home to colorful murals and zodiac statues.

Insider Tip: Don’t leave without trying bubble tea from Joy Yee or hand-pulled noodles from Lao Sze Chuan!

Nightlife & Rooftop Bars

Chicago’s nightlife is as vibrant as its skyline. It offers everything from rooftop bars with stunning views (like Cindy’s Rooftop and LH on 22) to legendary live music venues (such as Kingston Mines for blues and Smart Bar for EDM). If you’re looking for a chic cocktail lounge, The Violet Hour in Wicker Park is a must-visit speakeasy, while The Underground in River North is perfect for dancing the night away.

Additional information

Best time to visit

The best time to visit Chicago depends on what you’re looking for! Summer (June to August) is perfect for warm weather, lakefront activities, and festivals like Lollapalooza. But it’s also the busiest and most expensive season.

Spring (April to May) and fall (September to October) offer pleasant temperatures, fewer crowds, and stunning seasonal colors. It is perfect for exploring the city’s parks and outdoor attractions.

If you don’t mind the cold, winter (November to March) has its own charm, with festive holiday lights, ice skating at Millennium Park, and lower hotel rates. No matter when you visit, Chicago has something amazing to offer!

Final Thoughts

Chicago offers an unforgettable mix of iconic landmarks, cultural attractions, and vibrant neighborhoods. Whether you’re exploring historic sites, enjoying scenic parks, or indulging in local cuisine, there’s something for everyone. For more travel inspiration, check out Hochatown and Salt Lake City, Utah for unique experiences beyond the Windy City.