Top Attractions

Chicago's top attractions reflect a city that takes its architecture, art, and public spaces seriously. These are the must-see destinations that define the city.

Millennium Park & Cloud Gate

Millennium Park is the crown jewel of Chicago's public spaces. The iconic Cloud Gate sculpture — affectionately known as "The Bean" — is the most photographed spot in the city. In summer, catch free concerts at the Jay Pritzker Pavilion, designed by Frank Gehry. The Lurie Garden and Crown Fountain are equally worth exploring.

Art Institute of Chicago

Consistently ranked among the best art museums in the world, the Art Institute of Chicago houses an extraordinary collection that includes Georges Seurat's "A Sunday on La Grande Jatte," Grant Wood's "American Gothic," and Edward Hopper's "Nighthawks." The Modern Wing, designed by Renzo Piano, is stunning in its own right.

Willis Tower Skydeck

Take the elevator to the 103rd floor of the Willis Tower (formerly Sears Tower) and step onto The Ledge — a glass balcony extending 4.3 feet from the building, 1,353 feet above the street. On a clear day, you can see four states: Illinois, Indiana, Wisconsin, and Michigan.

Chicago Architecture River Cruise

Board a boat on the Chicago River for a 90-minute narrated tour past more than 40 notable buildings. The Chicago Architecture Foundation Center River Cruise is widely considered one of the best tours in any American city. You will see masterworks by Mies van der Rohe, Daniel Burnham, and Jeanne Gang.

Food & Dining Scene

Chicago is a serious food city with iconic dishes that have earned national fame and a thriving restaurant scene that goes far beyond deep-dish.

Must-Try Chicago Foods

  • Deep-Dish Pizza: Lou Malnati's and Giordano's are the two heavyweight contenders. For a lesser-known gem, try Pequod's in Lincoln Park, famous for its caramelized cheese crust that forms a crispy ring around the edge.
  • Chicago-Style Hot Dog: An all-beef frankfurter on a poppy seed bun topped with yellow mustard, relish, onion, tomato, pickle, sport peppers, and celery salt — never ketchup. Portillo's and Superdawg are institutions.
  • Italian Beef: Al's #1 Italian Beef on Taylor Street serves the definitive version — thinly sliced seasoned beef on Italian bread, dipped in jus, with hot giardiniera peppers. Order it "dipped" for the full experience.
  • Garrett Popcorn: The Chicago Mix — a blend of caramel and cheese popcorn — is an addictive local obsession available at Garrett Popcorn Shops throughout the city.

Neighborhood Food Crawls

Pilsen is the heart of Chicago's Mexican-American community, with outstanding taquerias and panaderias along 18th Street. Chinatown on the South Side offers authentic dim sum at MingHin Cuisine and hand-pulled noodles at Lao Sze Chuan. Devon Avenue on the Far North Side is a corridor of Indian, Pakistani, and Middle Eastern restaurants and grocery stores.

Outdoor Activities

Chicago's 26 miles of lakefront trail and 600-plus parks make it one of the greenest big cities in America.

Lakefront Trail

The 18.5-mile Lakefront Trail runs along Lake Michigan from Edgewater to the South Side, passing beaches, harbors, parks, and museums. It is perfect for running, cycling, or a leisurely walk. North Avenue Beach and Oak Street Beach are popular summer hangouts with skyline views.

Lincoln Park

This 1,200-acre park stretching along the North Side lakefront contains the free Lincoln Park Zoo, the Lincoln Park Conservatory, and miles of jogging paths. The Alfred Caldwell Lily Pool is a hidden oasis of native prairie plantings and a National Historic Landmark.

Kayaking the Chicago River

Paddle through the heart of downtown on a guided kayak tour of the Chicago River. Urban Kayaks and Wateriders offer tours that let you see the city's famous architecture from water level — a perspective few visitors experience.

Nightlife & Entertainment

Chicago's nightlife scene is legendary, rooted in blues, jazz, and comedy traditions that have shaped American culture.

Blues & Jazz

Kingston Mines in Lincoln Park is Chicago's premier blues club, with two stages running music until 4 AM on weekends. Buddy Guy's Legends in the South Loop is owned by the legendary guitarist himself. For jazz, the Green Mill Cocktail Lounge in Uptown — a former Al Capone haunt — hosts live jazz seven nights a week in a beautifully preserved Art Deco space.

Comedy

The Second City in Old Town launched the careers of Tina Fey, Steve Carell, and Bill Murray. Their mainstage and e.t.c. shows blend scripted sketches with improv. iO Theater and the Annoyance Theatre round out Chicago's legendary comedy scene.

Craft Beer

Chicago is a craft beer powerhouse. Revolution Brewing in Logan Square is the city's largest independent brewery. Half Acre Beer Company in North Center and Maplewood Brewery in Bucktown are excellent taproom destinations.

Hidden Gems

The 606 Trail

Chicago's answer to New York's High Line, the 606 is an elevated trail built on a former rail line running 2.7 miles through the neighborhoods of Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a fantastic urban walk with public art installations and neighborhood views that most tourists never discover.

Promontory Point

This man-made peninsula jutting into Lake Michigan in Hyde Park offers arguably the best skyline view in the city. Locals gather on the limestone steps for picnics and swimming. It is far from the tourist crowds and beloved by South Siders.

The Signature Room at the 95th

While tourists pay to visit the John Hancock Observatory, savvy locals head to the women's restroom at the Signature Room one floor below for equally stunning views — completely free. The bar serves cocktails with a 360-degree panorama that rivals any paid observation deck in the city.