Top 15 Things to Do in Chicago: Attractions, Dinning, Nightlife, Live Events, and More

Experience Chicago’s energy, from iconic landmarks to hidden gems, there’s always something to do in the Windy City.

Discover Chicago through its many attractions, shopping, dining, and downtown scene. Whether you’re a local or a visitor, there’s always something new to experience in Chicago. Located on the shores of Lake Michigan, Chicago is a bustling metropolis known for its stunning architecture, rich history, and diverse neighborhoods like Andersonville and Lake View. From the towering skyscrapers of the Loop to the historic charm of Wicker Park, the Windy City offers a unique blend of old and new. Visitors can explore world-renowned museums, indulge in delicious cuisine, and enjoy a variety of festivals and events that showcase the city’s dynamic spirit. With its lively music and nightlife scene, scenic parks, and shopping districts, Chicago has something new for anyone to enjoy.

So whether you are searching for apartments in Chicago, homes for sale, or are already a local, this Redfin article will be your guide. Here’s a list of the top 15 things to do in Chicago, for both newcomers and long-time locals alike.

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Tours and Attractions

1. The Art Institute of Chicago

Visit the Art Institute of Chicago to explore a vast collection of art from around the world, including iconic works like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.” This renowned museum offers both permanent exhibits and rotating special exhibitions, making each visit unique. Located in the heart of Grant Park, it’s easily accessible and a must-see for art enthusiasts.

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2. Willis Tower Skydeck

Experience breathtaking views from the Willis Tower Skydeck, where you can step onto “The Ledge,” a glass balcony extending four feet outside the 103rd floor. This iconic skyscraper provides panoramic views of Chicago’s skyline and beyond, perfect for photography and sightseeing. Be sure to visit during sunset for an unforgettable visual experience.

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3. Chicago River Architecture Tour

Discover Chicago’s architectural marvels with a guided tour along the Chicago River. This boat tour offers an insightful look at the city’s most famous buildings, their history, and the architectural styles that define Chicago. It’s an educational and scenic way to appreciate the city’s skyline from a unique perspective.

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Shopping and Dining

4. The Magnificent Mile

Explore The Magnificent Mile, Chicago’s premier shopping district, featuring over 460 stores, from high-end boutiques to popular retail chains. This bustling area also boasts a variety of dining options, ranging from quick bites to upscale restaurants, ensuring a satisfying shopping and culinary experience. Don’t miss the historic Water Tower Place for a mix of shopping and entertainment.

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5. Eataly Chicago

Immerse yourself in Italian culture at Eataly Chicago, a vibrant marketplace offering a variety of Italian foods, wines, and culinary products. You can dine at one of their many in-house restaurants, take a cooking class, or shop for gourmet ingredients to create your own Italian feast at home. It’s a food lover’s paradise located in the heart of the city.

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6. West Loop’s Randolph Street

Head to Randolph Street in the West Loop for a culinary adventure through Chicago’s renowned restaurant row. This area is packed with trendy eateries, from Michelin-starred establishments to casual cafes, offering a diverse range of cuisines. Make a reservation at one of the top spots to enjoy a gourmet meal and a vibrant dining atmosphere.

Music and Nightlife

7. The Green Mill Cocktail Lounge

Experience Chicago’s jazz scene at The Green Mill Cocktail Lounge, a historic bar that has hosted legendary musicians since the 1900s. Enjoy live jazz performances in a cozy, speakeasy-style setting, complete with classic cocktails and an intimate ambiance. This Uptown gem is a must-visit for music lovers.

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8. House of Blues Chicago

Catch a live performance at House of Blues Chicago, a vibrant venue known for its eclectic mix of musical acts, from rock and blues to hip-hop and country. Located in the historic Marina City complex, it also features a restaurant serving Southern-inspired dishes, making it a perfect spot for dinner and a show.

9. Smart Bar

Dance the night away at Smart Bar, one of Chicago’s premier nightclubs known for its cutting-edge electronic music scene. Located in the basement of Metro, this club features top local and international DJs, providing an energetic atmosphere for dance music enthusiasts. It’s a staple of Chicago’s nightlife, perfect for those looking to experience the city’s club culture.

Festivals and Events

10. Chicago Blues Festival

Celebrate Chicago’s rich musical heritage at the Chicago Blues Festival, the largest free blues festival in the world. Held annually in Millennium Park, this event features performances by top blues artists, both legendary and contemporary. It’s a great opportunity to enjoy live music in a scenic outdoor setting.

11. Taste of Chicago

Savor the diverse flavors of the city at Taste of Chicago, an annual food festival held in Grant Park. This event showcases a variety of local restaurants and food vendors, offering everything from deep-dish pizza to international cuisine. It’s a food lover’s dream, complete with live music and friendly activities.

12. Chicago Air and Water Show

Witness thrilling aerial displays and water stunts at the Chicago Air and Water Show, held along the city’s lakefront. This free event attracts millions of spectators and features performances by the U.S. Navy Blue Angels and other military and civilian pilots. It’s a spectacular showcase of aviation and maritime skills, perfect for a summer outing.

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Outdoor Activities and Parks

13. Millennium Park

Stroll through Millennium Park, home to iconic attractions like Cloud Gate (The Bean), Crown Fountain, and the Jay Pritzker Pavilion. This urban oasis offers lush green spaces, public art installations, and cultural events throughout the year. It’s a perfect spot for a walk, a picnic, or attending a free concert.

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14. Lincoln Park Zoo

Visit the Lincoln Park Zoo, one of the oldest zoos in the country and free to the public. Located in the scenic Lincoln Park neighborhood, it houses a diverse range of animals and offers educational programs and friendly activities. The zoo’s beautiful gardens and historic architecture add to its charm.

15. Lakefront Trail

Enjoy a scenic bike ride or walk along the Lakefront Trail, a 18-mile path that stretches from Ardmore Avenue on the North Side to 71st Street on the South Side. This trail offers stunning views of Lake Michigan and the Chicago skyline, with plenty of beaches, parks, and attractions along the way. It’s an ideal route for outdoor enthusiasts looking to explore the city’s waterfront.

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