A Comprehensive Guide to Things to Do in Chicago

Chicago, known as the Windy City, is a vibrant metropolis that offers a diverse array of activities and attractions for all interests. Here’s a guide to help you make the most of your visit.

Must-Visit Attractions

Millennium Park

Millennium Park is one of Chicago’s top bucket list contenders. Here, you can admire the stunning architecture, sculpture, and landscape design. Key highlights include:

  • Cloud Gate (The Bean): A polished steel sculpture that reflects the city skyline.
  • Crown Fountain: Features towering faces of Chicagoans and an interactive water display.
  • BP Bridge: A 935-foot-long winding walkway offering spectacular views of the Chicago skyline[1][4][5].

Grant Park

Located nearby, Grant Park is a 319-acre green space that houses several notable attractions:

  • Buckingham Fountain: One of the largest fountains in the world, known for its dazzling water displays and evening light shows[1][5].

Museum Campus

This 57-acre park by Lake Michigan is home to several world-class museums:

  • Shedd Aquarium: Features a variety of marine life and interactive exhibits.
  • Field Museum of Natural History: Known for its extensive collection of natural history specimens and artifacts.
  • Adler Planetarium: Offers stunning views of the city and interactive astronomy exhibits[2][4][5].

Outdoor Activities

Maggie Daley Park

This park is a vibrant oasis in the heart of the city, offering:

  • Rock Climbing: Walls for all skill levels with the Chicago skyline as a backdrop.
  • Tennis Courts and Picnic Groves: Perfect for a leisurely day out.
  • Expansive Play Areas: Including mini golf and skating rinks[3][4].

The 606 (Bloomingdale Trail)

This elevated linear park is a unique outdoor space:

  • Walking, Running, and Cycling: Offers a perspective on Chicago’s neighborhoods, art installations, and nature.
  • Community Activities: Includes bird watching and community yoga sessions[3][4].

Chicago Riverwalk

The Riverwalk is a great place to enjoy the city’s architecture, public art, and dining venues:

  • Kayaking: Paddle past iconic landmarks like the Willis Tower and Merchandise Mart.
  • Art on the Mart: A digital art projection visible between May and December[3][4].

Cultural and Historical Experiences

Art Institute of Chicago

One of the oldest and largest art museums in the country, featuring a vast collection of art from around the world[1][4].

Chicago Cultural Center

This historic building offers free exhibitions, concerts, and events. It is also a great place to start your exploration of the city’s cultural scene[1].

Chicago Architecture Center

Located near the river, the Chicago Architecture Center offers:

  • Skyscraper Models and City Models: Detailed models of Chicago’s iconic buildings and a large-scale model of the city.
  • Architecture River Cruises: Led by knowledgeable docents, these cruises provide a deep dive into Chicago’s architectural history[1][4].

Entertainment and Nightlife

Rooftop Dining and Drinks

Enjoy panoramic views of the city from rooftops like:

  • Cindy’s Rooftop: Located in the Chicago Athletic Association Hotel, offering fresh seasonal produce and a great cocktail menu.
  • J. Parker: Atop Hotel Lincoln in Lincoln Park, providing full meals and skyline views[4].

Navy Pier

This popular attraction offers:

  • The Centennial Wheel: A Ferris wheel with enclosed gondolas.
  • Shopping, Dining, and Entertainment: Museums, theaters, and live performances[4][5].

Jazz and Blues Clubs

Chicago is renowned for its jazz and blues scene. Spend an evening listening to local legends at various clubs around the city[1].

Sports and Recreation

Lincoln Park Zoo

A free zoo located in Lincoln Park, offering a blend of nature and wildlife in an urban setting[2][3].

Wrigley Field

For sports fans, Wrigley Field, the home of the Chicago Cubs, is a must-visit. It is surrounded by the bustling bars and restaurants of Wrigleyville[4].

Other Notable Attractions

Willis Tower (Skydeck Chicago)

For a panoramic view of the city from above, visit the Skydeck on the 103rd floor of the Willis Tower[2][4].

The Magnificent Mile

This famous stretch along Michigan Avenue is known for its upscale shopping, dining, and entertainment[5].

Most Important Facts About Things to Do in Chicago

  • Millennium Park: Home to iconic landmarks like Cloud Gate (The Bean) and Crown Fountain.
  • Grant Park: Features Buckingham Fountain, one of the largest fountains in the world.
  • Museum Campus: Includes the Shedd Aquarium, Field Museum of Natural History, and Adler Planetarium.
  • Maggie Daley Park: Offers rock climbing, tennis courts, picnic groves, and expansive play areas.
  • The 606 (Bloomingdale Trail): An elevated linear park for walking, running, and cycling.
  • Chicago Riverwalk: Perfect for kayaking, public art, and dining venues.
  • Art Institute of Chicago: One of the oldest and largest art museums in the country.
  • Chicago Architecture Center: Offers detailed models and architecture river cruises.
  • Rooftop Dining: Enjoy panoramic views at Cindy’s Rooftop and J. Parker.
  • Navy Pier: Features The Centennial Wheel, shopping, dining, and entertainment.
  • Willis Tower (Skydeck Chicago): Offers panoramic views of the city from the 103rd floor.
  • Wrigley Field: The home of the Chicago Cubs, surrounded by Wrigleyville’s bars and restaurants.

Whether you’re interested in art, architecture, outdoor activities, or entertainment, Chicago has something for everyone.