40 Best Things to Do in Chicago, From Iconic Sights to Can't-miss Museums

Iconic Chicago Landmarks

No trip to Chicago is complete without experiencing its most famous landmarks. These architectural marvels and historical sites are quintessential Chicago.

• Millennium Park: Home to the iconic Cloud Gate ("The Bean") and the Crown Fountain, Millennium Park is a must-see.
• Navy Pier: Enjoy stunning lake views, amusement rides, and a variety of entertainment options at this popular pier.
• Willis Tower (formerly Sears Tower): Ascend to the Skydeck for unparalleled panoramic views of the city.
• John Hancock Center: Another skyscraper offering breathtaking views, including the "Tilt" experience.
• Wrigley Building: Admire the stunning architecture of this iconic building on Michigan Avenue.

World-Class Museums

Chicago boasts an impressive collection of museums, covering everything from art and science to history and culture. Prepare to be amazed by the diverse exhibits and collections.

• Art Institute of Chicago: Home to masterpieces like Grant Wood's "American Gothic" and Edward Hopper's "Nighthawks."
• Field Museum: Explore natural history exhibits, including Sue, the largest and most complete Tyrannosaurus rex fossil ever found.
• Museum of Science and Industry: Engage with interactive exhibits covering science, technology, engineering, and math.
• Shedd Aquarium: Discover a diverse array of aquatic life, from beluga whales to colorful coral reefs.
• Chicago History Museum: Learn about the rich history of Chicago, from its early days to the present.

Exploring Chicago's Neighborhoods

Each of Chicago's neighborhoods has its unique character and charm. Venture beyond downtown to discover hidden gems and local favorites.

• River North: Known for its art galleries, upscale restaurants, and vibrant nightlife.
• Lincoln Park: Home to Lincoln Park Zoo (free!), beautiful parks, and charming boutiques.
• Wicker Park/Bucktown: A trendy neighborhood with independent shops, live music venues, and delicious restaurants.
• Pilsen: A historically Czech and Mexican neighborhood with colorful murals, authentic cuisine, and a thriving arts scene.
• Hyde Park: Home to the University of Chicago and the Museum of Science and Industry, this neighborhood offers a mix of intellectual and cultural experiences.

Outdoor Activities and Recreation

Take advantage of Chicago's beautiful lakefront and parks for outdoor adventures.

• Lakefront Trail: Bike, walk, or run along this scenic trail that stretches along Lake Michigan.
• Chicago Riverwalk: Stroll along the riverwalk, enjoy outdoor dining, and take in the city views.
• Lincoln Park Zoo: A free zoo offering a diverse collection of animals.
• Kayaking on the Chicago River: Experience the city from a unique perspective by kayaking on the Chicago River.
• Beach Day at North Avenue Beach: Relax on the sand, swim in the lake, and enjoy the vibrant atmosphere.

Food and Drink Adventures

Chicago is a foodie paradise, offering a wide range of culinary experiences. Don't miss out on these iconic Chicago foods and drinks.

• Deep-Dish Pizza: Indulge in a classic Chicago deep-dish pizza.
• Chicago-Style Hot Dog: Try a hot dog topped with mustard, relish, onions, tomatoes, sport peppers, a pickle, and celery salt (no ketchup!).
• Italian Beef Sandwich: Savor a delicious Italian beef sandwich, dipped in au jus.
• Craft Beer Scene: Explore Chicago's thriving craft beer scene, with numerous breweries and brewpubs.
• Fine Dining Restaurants: Experience world-class cuisine at one of Chicago's many fine dining restaurants.

Arts, Culture, and Entertainment

Chicago is a hub for arts, culture, and entertainment. From live music to theater performances, there's something for everyone.

• Broadway in Chicago: Catch a Broadway show at one of Chicago's historic theaters.
• Second City: Experience improvisational comedy at the legendary Second City theater.
• Live Music Venues: Discover a diverse range of live music venues, from intimate clubs to large concert halls.
• Chicago Theatre: Admire the stunning architecture of the Chicago Theatre and catch a show.
• Grant Park Music Festival: Enjoy free classical music concerts in Grant Park during the summer.

Unique Experiences

Looking for something a little different? Check out these unique experiences in Chicago.

• Architectural Boat Tour: Learn about Chicago's architectural history on a boat tour of the Chicago River.
• Gangsters and Ghosts Tour: Explore Chicago's history of gangsters and ghosts on a guided tour.
• Chicago Greeters: Take a free walking tour led by a local volunteer.
• Garrett Popcorn Shops: Sample the famous Garrett Mix popcorn (cheese and caramel).
• Shopping on Michigan Avenue (Magnificent Mile): Browse the high-end shops and department stores on Michigan Avenue.

Chicago at a Glance: Top Activities by Category

Here's a quick overview to help you prioritize your Chicago itinerary:

With so much to see and do, Chicago is a city that will leave you wanting more. Whether you're interested in history, culture, food, or outdoor adventures, the Windy City has something for everyone. Start planning your trip today and discover the magic of Chicago!