30 Things to Do in Chicago
Chicago, the vibrant metropolis on the shores of Lake Michigan, impresses visitors with its stunning architecture, world-class museums, passionate sports culture, and legendary food scene. Planning your trip involves seeking out iconic architectural tours Chicago offers, hunting down the best deep dish pizza Chicago is famous for, exploring diverse neighborhoods, and discovering the many fantastic free things to do in Chicago, like relaxing in Millennium Park or strolling the lakefront. This city offers a dynamic blend of Midwestern friendliness and big-city excitement.
From gazing down from towering skyscrapers to laughing at legendary comedy clubs and savoring local flavors, Chicago delivers a rich array of experiences. This guide presents 30 distinct activities, combining famous landmarks with beloved local traditions and neighborhood explorations. Use these suggestions to build your Chicago itinerary and dive into the energetic spirit of the “Windy City.”
Iconic Landmarks and Lakefront Views
Step out onto The Ledge at Skydeck Chicago in Willis Tower for thrilling views from glass boxes extending out from the 103rd floor. See unparalleled perspectives of the cityscape stretching out below you.
Experience TILT at 360 CHICAGO atop the former John Hancock Center, where you can tilt outwards over Michigan Avenue from 1,000 feet up. The observation deck itself offers stunning lake and skyline views.
Take a selfie with Cloud Gate (The Bean) in Millennium Park, Anish Kapoor’s iconic, mirror-like sculpture reflecting the city skyline. Walk around and under it to see the distorted reflections change.
Watch the spectacular water display at Buckingham Fountain in Grant Park (seasonal, typically May-October). Its impressive evening light and music shows are a classic Chicago experience.
Ride the Centennial Wheel at Navy Pier for fantastic views of the Chicago skyline and Lake Michigan. The pier itself offers entertainment, dining, boat tours, and seasonal events.
Stroll or bike along the Lakefront Trail, stretching 18 miles along Lake Michigan’s shore. Enjoy beautiful views of the water, parks, and city skyline, accessing beaches and harbors along the way.
Walk the scenic Chicago Riverwalk, a pedestrian path along the south bank of the main branch of the Chicago River downtown. Find restaurants, bars, boat tour docks, and public art installations.
Take an Architecture River Cruise, widely considered a must-do Chicago activity. Knowledgeable guides narrate the history and design of the city’s famed skyscrapers lining the river.
World-Class Museums and Culture
Explore the vast collections of the Art Institute of Chicago, one of the world’s top art museums, housing masterpieces from Impressionism to modern art. Plan several hours to appreciate highlights like works by Monet, Renoir, and Seurat’s “A Sunday on La Grande Jatte”.
Meet SUE the T. rex and explore exhibits on natural history and world cultures at the Field Museum. Discover ancient Egyptian tombs, gemstones, and exhibits covering biology and anthropology.
Engage with interactive exhibits covering physics, transportation, weather, and more at the Museum of Science and Industry. Explore a German U-boat, a coal mine replica, and countless hands-on displays.
Look to the stars at the Adler Planetarium, America’s first planetarium, located on the Museum Campus jutting into Lake Michigan. Enjoy sky shows and exhibits on astronomy and space exploration, plus great skyline views.
Discover the aquatic world at the Shedd Aquarium, home to thousands of species from oceans, rivers, and lakes around the globe. See beluga whales, dolphins, penguins, and vibrant coral reef exhibits.
Visit the Chicago History Museum in Lincoln Park to learn about the city’s past, from its founding to major events like the Great Chicago Fire. Explore exhibits on politics, culture, and influential figures.
Parks and Green Escapes
Relax in Millennium Park, home to The Bean, Crown Fountain, Lurie Garden, and the Jay Pritzker Pavilion. Enjoy public art, free concerts and events (seasonal), and beautiful landscaping downtown.
Explore Grant Park, often called “Chicago’s front yard,” stretching along the lakefront and encompassing Millennium Park, Buckingham Fountain, and several major museums. It hosts large events like Lollapalooza.
Visit the Lincoln Park Zoo, one of the oldest and last free-admission zoos in the country, located within the sprawling Lincoln Park. See animals from around the world in naturalistic habitats.
Play at Maggie Daley Park, adjacent to Millennium Park, featuring imaginative playgrounds, climbing walls, and a unique skating ribbon (ice in winter, roller/scooter in summer). It’s fantastic fun for families.
Escape into tropical warmth year-round at the Garfield Park Conservatory, one of the largest conservatories in the US. Wander through stunning indoor gardens showcasing thousands of plant species under glass.
Foodie Favorites
Indulge in Chicago’s famous deep-dish pizza at iconic spots like Lou Malnati’s, Pizzeria Uno/Due, or Giordano’s. Prepare for a thick crust, layers of cheese, toppings, and sauce served in a pan.
Try an authentic Chicago-style hot dog, typically an all-beef frankfurter “dragged through the garden” with yellow mustard, chopped onions, bright green relish, tomato slices, sport peppers, a pickle spear, and celery salt on a poppy seed bun. Ketchup is famously frowned upon.
Sample Garrett Popcorn’s “Garrett Mix” (formerly Chicago Mix), a signature blend of caramel crisp and cheese corn. Find their shops downtown and prepare for potentially long, but worthwhile, lines.
Savor a classic Italian Beef sandwich, featuring thinly sliced seasoned roast beef simmered in jus, served on Italian bread, often dipped (“wet”) and topped with sweet peppers or spicy giardiniera. It’s a messy but beloved local specialty.
Take a Chicago food tour exploring specific neighborhoods like the West Loop or River North. Sample various local specialties while learning about the city’s culinary history.
Neighborhood Exploration and Shopping
Shop designer boutiques and major department stores along The Magnificent Mile, a prestigious stretch of North Michigan Avenue. Enjoy the upscale atmosphere, beautiful architecture, and people-watching.
Explore the trendy neighborhoods of Wicker Park and Bucktown, known for independent boutiques, vintage shops, record stores, art galleries, and hip restaurants. Wander Damen Avenue and Milwaukee Avenue to soak in the vibe.
Visit Wrigleyville, the neighborhood surrounding historic Wrigley Field, especially vibrant on game days for the Chicago Cubs. Experience the lively sports bars and unique baseball atmosphere.
Explore the charming Lincoln Park neighborhood beyond the zoo and park itself. Stroll Armitage Avenue or Halsted Street for boutiques, cafes, and beautiful brownstone-lined streets.
Walk through The Loop, Chicago’s central business district, to admire iconic architecture, public art (like the Picasso sculpture), and the bustling energy of downtown. Look up to appreciate the skyscraper details.
Discover the vibrant murals and rich Mexican-American culture in the Pilsen neighborhood. Explore the National Museum of Mexican Art (free admission) and enjoy authentic cuisine.
Arts and Entertainment
See a Broadway show or pre-Broadway production in Chicago’s vibrant Theater District located in the Loop. Find historic venues like the Cadillac Palace Theatre or the Nederlander Theatre.
Laugh out loud at a comedy show at The Second City in Old Town, the legendary improv theater known for launching the careers of countless famous comedians. Book tickets in advance for this popular spot.
Listen to authentic live blues music at legendary clubs like Buddy Guy’s Legends or Kingston Mines. Experience the genre deeply rooted in Chicago’s musical heritage.
