15 Things to do in Chicago: Travel Guide to Windy City’s Must-See Spots

Exploring Chicago feels like diving into an exciting mix of vibrant city life, impressive architecture, rich cultural scenes, and delightful culinary adventures. As a digital nomad who loves discovering new cities, Chicago captivated me instantly with its unique charm, bustling streets, and friendly locals.

Known as the Windy City, Chicago effortlessly blends modern sophistication with historical allure, creating an ideal destination for urban explorers and culture lovers.

Whether strolling along Lake Michigan’s scenic shoreline, sampling the city’s famous deep-dish pizza, or wandering through world-class museums, there’s something incredible for every traveler here. To help you experience the best this city has to offer, here’s my list of 15 unforgettable things to do in Chicago!

1. Take in the Views at Willis Tower Skydeck

Experience awe-inspiring views at the Willis Tower Skydeck, one of Chicago’s most iconic landmarks. Located on the 103rd floor, it offers a breathtaking panorama of the city skyline, stretching across four states on clear days.

If you’re brave, step onto The Ledge—glass balconies extending over four feet outside the building’s facade, providing exhilarating views directly beneath your feet. Ideal for memorable photos, especially at sunset when the city lights begin to sparkle, the Skydeck is an absolute must-visit attraction.

Expect queues during peak times; arriving early or booking tickets online can save time and make your experience smoother and more enjoyable.

2. Explore Millennium Park

Millennium Park is a vibrant urban oasis in downtown Chicago, perfect for leisurely strolls, picnics, or enjoying free outdoor events. Don’t miss the famous Cloud Gate sculpture, affectionately known as “The Bean,” where visitors take creative reflections selfies.

Nearby, the Crown Fountain displays animated faces spouting water—ideal for cooling off on a sunny day. The Jay Pritzker Pavilion hosts concerts, movie screenings, and festivals regularly. Enjoy beautifully landscaped gardens, art installations, and impressive architecture throughout the park.

Whether exploring solo or relaxing with friends, Millennium Park offers delightful experiences blending nature, art, and culture seamlessly into Chicago’s bustling heart.

3. Visit the Art Institute of Chicago

Art lovers must visit the Art Institute of Chicago, home to an extensive collection of masterpieces from famous artists like Monet, Van Gogh, and Picasso. This acclaimed museum houses over 300,000 artworks ranging from ancient artifacts to contemporary pieces.

Notable highlights include American Gothic by Grant Wood, Van Gogh’s Bedroom in Arles, and Monet’s iconic Water Lilies. Take your time exploring diverse exhibits spread across several floors, each offering a rich cultural journey through history and creativity.

Guided tours or audio guides enhance your understanding, providing interesting stories behind each artwork, making your visit both educational and visually inspiring.

4. Wander Around Navy Pier

Navy Pier is a lively entertainment hub along Lake Michigan, popular among both locals and visitors. Home to iconic attractions such as the Centennial Wheel, offering stunning lakefront and cityscape views, Navy Pier promises fun-filled experiences for everyone.

Explore charming shops, cafes, and eateries offering delicious local treats and international cuisines. Kids and adults alike will enjoy interactive museums, mini-golf courses, and frequent live music performances.

Firework displays, held regularly during summer evenings, provide an unforgettable visual spectacle. Whether taking a romantic evening stroll or spending a joyful family day, Navy Pier ensures endless entertainment and memories.

5. Indulge in Chicago’s Deep-Dish Pizza

Your trip to Chicago isn’t complete without savoring its famous deep-dish pizza. Chicago-style pizza is unique, featuring a thick buttery crust, generous amounts of cheese, chunky tomato sauce, and hearty toppings.

Popular spots like Lou Malnati’s, Giordano’s, or Pequod’s offer authentic deep-dish experiences. Be prepared for longer wait times as these pizzas are freshly baked to perfection—usually around 30-45 minutes.

It’s more than just a meal; it’s a delicious cultural experience that will surely become a favorite culinary memory. Make sure to come hungry; portions are delightfully generous!

6. Discover Chicago’s Riverwalk

Chicago’s Riverwalk is a picturesque walkway along the Chicago River, featuring delightful restaurants, cozy cafes, public art installations, and lush green spaces.

Ideal for leisurely strolls, cycling, or simply enjoying spectacular city views, this vibrant area invites visitors to relax and unwind amidst the urban landscape. Consider taking a scenic boat tour or a kayaking adventure to explore the city’s impressive architecture from a unique water-level perspective.

In warmer months, street performances, music events, and food festivals frequently occur along the Riverwalk, adding lively entertainment to your exploration. This area beautifully combines city charm with serene waterfront relaxation.

7. Stroll Through Lincoln Park Zoo

Lincoln Park Zoo, nestled within the lush Lincoln Park, is one of America’s oldest zoos and offers free admission year-round. Home to hundreds of animal species, including lions, giraffes, penguins, and gorillas, the zoo offers educational and engaging experiences suitable for all ages.

Explore beautifully designed exhibits mimicking natural habitats, ensuring ethical and enriching environments for wildlife. Regularly scheduled feeding sessions, interactive experiences, and informative talks by zookeepers enhance your visit.

After exploring the zoo, stroll through scenic Lincoln Park, enjoying gardens, conservatories, and picturesque lakeside trails, making it a perfect day out for nature lovers.

8. Catch a Game at Wrigley Field

Baseball enthusiasts shouldn’t miss the chance to experience a live game at the historic Wrigley Field, home to the Chicago Cubs. Built in 1914, Wrigley Field has retained its nostalgic charm, complete with iconic ivy-covered outfield walls and vintage scoreboard.

The electric atmosphere during game days, enthusiastic fans, and traditional ballpark food make attending a game here unforgettable. Even if you’re not a baseball fan, the vibrant neighborhood surrounding Wrigleyville is bustling with sports-themed bars, quirky shops, and lively entertainment venues, ensuring a memorable experience beyond the game itself.

9. Relax at North Avenue Beach

North Avenue Beach is a popular summertime destination offering golden sands, clear waters, and incredible city skyline views. It’s perfect for sunbathing, swimming, beach volleyball, or cycling along the lakeshore path.

The beach also hosts vibrant events like music festivals and volleyball tournaments throughout summer. Grab snacks or refreshments at nearby eateries or cafes lining the beachfront promenade. With ample amenities, including changing rooms, rental equipment, and lifeguards, it’s an ideal spot for a relaxing beach day amidst urban convenience.

10. Experience The Magnificent Mile

Chicago’s Magnificent Mile is a bustling shopping district stretching along Michigan Avenue. Home to upscale boutiques, luxury department stores, trendy retailers, and charming cafes, it offers a delightful shopping experience catering to all tastes.

Beyond shopping, admire historic buildings, contemporary architecture, and vibrant street scenes. Frequent events, street performances, and seasonal decorations enhance the experience, especially during the festive holiday period when the avenue sparkles with dazzling lights and decorations.

11. Visit Shedd Aquarium

Shedd Aquarium is a fascinating aquatic world housing over 32,000 marine animals from around the globe. Explore immersive exhibits featuring diverse species, including dolphins, beluga whales, penguins, sharks, and colorful coral reef fish.

Engaging presentations and interactive feeding demonstrations provide educational insights into marine life and conservation efforts. The aquarium’s architecture is equally impressive, beautifully situated along Lake Michigan, offering stunning views from its expansive outdoor terraces.

12. Explore the Field Museum

The Field Museum offers intriguing exhibitions on natural history and cultural anthropology, home to the famous Sue, the world’s largest T-Rex skeleton. Wander through expansive halls featuring dinosaur fossils, ancient Egyptian artifacts, precious gemstones, and wildlife displays.

Interactive exhibits and immersive multimedia presentations captivate visitors, providing enriching experiences suitable for all ages. It’s an educational and entertaining visit combining history, science, and culture seamlessly.

13. Admire Buckingham Fountain

Buckingham Fountain, located in Grant Park, is one of the largest fountains globally, beautifully illuminated with nightly water and light shows. The stunning fountain symbolizes Lake Michigan, showcasing captivating hourly water displays accompanied by synchronized music and lights.

Surrounded by lush gardens, walking paths, and impressive city views, it’s a perfect spot for romantic strolls, photography, or simply enjoying peaceful moments in the city.

14. Shop and Dine at Fulton Market

Fulton Market is Chicago’s trendy neighborhood, famous for chic boutiques, gourmet eateries, and vibrant nightlife. Renowned chefs operate award-winning restaurants featuring innovative cuisine, fresh ingredients, and creative dishes.

Explore boutique shops, galleries, and bustling markets offering unique goods and local products. The district buzzes with energy, attracting foodies, fashionistas, and art enthusiasts alike, making it an exciting area for dining and cultural exploration.

15. Enjoy Comedy at Second City

Second City, Chicago’s legendary comedy club, has launched numerous comedic talents like Tina Fey and Steve Carell. Experience hilarious live improv shows and sketch comedy performances showcasing top-notch comedic talent.

Offering laugh-out-loud entertainment, this iconic theater promises unforgettable evenings filled with laughter, witty humor, and interactive fun. It’s an essential experience for anyone seeking entertainment in Chicago’s rich cultural scene.