It’s no surprise that Chicago is one of the biggest tourist destinations: we have miles of beaches, world-class museums, and some of the friendliest city-dwellers out there. But in such a gigantic city, it can be tough for visitors to know what’s really worth visiting. So whether you’re an out-of-towner or a Chicagoan planning a staycation, we’ve assembled the 25 must-see sites and attractions in Chicago for your touring convenience. Oh, and if you’re feeling decadent, cap off your day of sightseeing with a meal at one of Chicago’s best restaurants.
Best attractions in Chicago
This 24.5-acre park features Frank Gehry's Pritzker Pavilion and serpentine bridge; sculptor Anish Kapoor's 110-ton Cloud Gate (a.k.a. “The Bean”); and Jaume Plensa's Crown Fountain, with its ever-changing array of locals' faces spewing water very five minutes in the summer months. The Lurie Garden wows with year-round flower displays and monthly garden walks.
You could spend the next four years getting to know this encyclopedic institution, which owns more than 300,000 artworks and artifacts from all over the world and every era from antiquity to the present. Our favorite pieces include the Japanese prints, fragments of local buildings by Frank Lloyd Wright and the Thorne Miniature Rooms. We’re also in love with Renzo Piano’s light-filled Modern Wing, which is the perfect place to enjoy the Art Institute’s architecture and design collection, modern and contemporary art, and gorgeous views of Millennium Park.
Even when baseball’s not in season, there’s plenty to do at this legendary stadium, erected in 1914 and reinvigorated by an ownership change in 2009. Seasonal tours offer an insider peek at the Friendly Confines when the Cubs are on the road or away for spring training.
Formerly known as the John Hancock Observatory, 360 Chicago offers dining, sights and an interactive tour far above the city streets. From 1,000 feet up on the 94th floor, you can see up to 55 miles out and four states—you'll feel as if you're along for the ride as you watch airplanes whiz by. A recent addition is the Tilt attraction, which allows visitors to step onto an enclosed platform that extends from the building at a 30 degree angle.
Even if you know nothing about improv, chances are you've heard of Second City. This is the place that put both sketch and improvised comedy on the map while launching the careers of many distinguished comics including Bill Murray, Tina Fey, Chris Farley, John Belushi, Joan Rivers, Stephen Colbert and Steve Carell. Mainstage revues are occasionally stodgy, but most shows are still top-notch.
Founded to house the biological and anthropological collections assembled for the World’s Columbian Exposition of 1893, this massive natural history museum still packs ’em in with more than 30 permanent exhibitions covering 300,000 square feet. Inside the permanent displays, you can see glowering dinos, marvel at ancient artifacts from a royal Egyptian tomb, check out artifacts in the Cyrus Tang Hall of China or take a stroll through the newly rehabbed Halls of Gems and Jade.
Described as “landscape art under glass” when it opened in 1908, the conservatory, while being one of the largest in the world, also boasts revolutionary architecture. With the building’s haystack shape and walls of stratified stonework, landscape architect Jens Jensen considered the Fern Room in particular, with its “prairie waterfall”—a stone and water element within a glass structure—to be one of his greatest achievements. About 120,000 plants representing some 600 species occupy the conservatory’s 1.6 acres, and four times a year flower shows premiere to herald the change in seasons.
Housing of one of the largest collections of modern art in the nation, the Museum of Contemporary Art also hosts major touring exhibits, film screenings and performing artists. When they're not browsing the extensive galleries, visitors can grab a bite to eat at the on-site restaurant or take a stroll through a picturesque sculpture garden. Don't forget to exit through the gift shop—it boasts one of the city's best selections of offbeat tchotchkes.
See some 1,200 animals, from apes to zebras, at the oldest and one of only a few free zoos left in the country. It is small, only 35 acres, but attractions like the Kovler Lion House and the Regenstein Center for African Apes pack a big punch. The newest feature: The Regenstein Macaque Forest, where snow monkeys swing through trees and relax in a hot tub.
A formerly abandoned stretch of elevated railway track that runs through Logan Square, Humboldt Park, Wicker Park and Bucktown has found new life as the 606. Named after the first three digits in every Chicago zip code, the 2.7-mile path provides a quick way to travel east and west on the North Side, connecting several parks and public art installations. Prepare to dodge strollers, bicycles and residents out for a very slow jog on this popular throughway.
If you’re into exhibits loaded with interactive bells and whistles, this expansive Hyde Park locale is your ticket. The museum’s focus is broad, with permanent displays that include the popular mirror maze in the "Numbers in Nature"exhibit, the whiz-bang "Science Storms," plus the old faves: a restored U-505 German submarine, a simulated coal mine and a vintage diesel-electric train.
Though it’s staffed by world-class researchers at the forefront of their field, the museum’s real draw will always be the virtual-reality trips through time and space in the Sky Theater, which features the "highest resolution and quality possible." Themes usually center around the known and unknown universe and how humans have engaged with it throughout history. The recently renovated "Mission Moon" exhibit allows visitors to see the Gemini 12 capsule and learn more about the early days of the space race.
You don't have to look any further than Pilsen to find one of the largest Latino cultural organizations in the U.S. Visit the National Museum of Mexican Art and explore a 6,000-piece permanent collection, rotating exhibits, performing-arts showcases and educational programming that represents an illustrious Mexican culture.
This 1973 landmark put the city in an uproar when insurance broker Willis Group Holdings Ltd acquired the Sears Tower naming rights in 2009. That doesn't change the fact that the building occupies two city blocks and stretches 1,454 feet high, making it the second-tallest building in the U.S. Skydeck views from the 103rd floor allow you to see as far as 50 miles out. While you’re up there, learn about the city’s landmarks from a multilingual computer program and about its history from wall exhibits. If the Skydeck’s newest feature, The Ledge sounds like a horror movie, there’s a reason for that: Crawl into the glass cube structure, and you’re suspended 1,353 feet off the ground.
Anchoring the aquatic offerings at this 75-year-old institution are enduring favorites such as piranhas, frogs and snakes of the Amazon; rays, turtles and moray eel of the Caribbean; frightening predator sharks and, the most storied of them all, a 100-plus-year-old Australian lungfish believed to be the longest-living fish in any aquarium in the world. A 2009 rehab of the Oceanarium gave Shedd a lifelike river and tide-pool, a reworked otter habitat, and an attempt to revamp its daily mammal presentations with choreography.
For movie lovers who don't care for traditional Hollywood blockbusters, there's no better theater than the Music Box, a two-screen cinema that shows the latest art-house films and documentaries. It's gorgeous, and the main theater regularly hosts director Q&A's as well as weekly midnight screenings of cult classics. Also, the concession stand here tops its popcorn with real butter.
On the one hand, the BOKA Restaurant Group’s year-round rooftop bar is unlike any other in the city: It boasts destination-themed cocktails, seasonal small-plates and sweeping, mesmerizing, breathtaking views of Lincoln Park from the 13th-floor roof of the Hotel Lincoln. On the other hand, it’s still a rooftop bar, which means you might need to sacrifice your first-born just to get a seat.
This tourist hot spot features shops, eateries, an IMAX cinema and a bevy of sightseeing boat tours. Pier Park is home to a 150-foot-high Ferris wheel, plus an old-fashioned swing ride and 18-hole mini-golf course. You'll also find the Chicago Children's Museum and a rotating roster of live entertainment on the Family Pavilion Stage. Most offerings may not turn locals on, but the seasonsal events, indoor activities and great people-watching provide plenty of entertainment, no matter what the weather.
From prairie and river ecosystems to the biology of Ice Age–mammals, nature and its conservation, the focus at this Lincoln Park museum situated alongside a lagoon is vast and varied. Hands-on interactive displays on marsh and river ecosystems engage kids, while the thousand fluttering beauties of the 2,700-square-foot Judy Istock Butterfly Haven appeal to all ages.
The newest jewel in the Chicago music scene, this antique concert hall in Pilsen was rehabbed and reopened by Empty Bottle owners Bruce Finkelman and Craig Golden, in the grand space above their restaurant and bar—Dusek's Board and Beer and Punch House. A balcony wraps around the room and opera boxes hang above the stage, and you can sit inside them for a price during select shows. The bookings lean a little City Winery, a little Empty Bottle (of course)—ranging from Americana to psychedelic.
Since being converted to the Cultural Center in 1991 (it used to be the Chicago Public Library), this city-block-wide institution now offers free classical concerts Mondays, Wednesdays and Sundays. Most of the center’s classical offerings take place in Preston Bradley Hall on the second floor near the Washington Street entrance, but the Claudia Cassidy Theater (named for the Tribune’s venom-penned theater and music critic from the ’40s) on the Randolph Street side is used for experimental concerts, too. Concerts are always free.
Al Capone and other gangsters used to hang here in the 1920s, but these days it’s all about the music. Owner Dave Jemilo, who returned the club to its original luster in the 1980s, books smart bebop and free jazz with a discriminating ear. Check out the weekly variety series Paper Machete on Saturday afternoons or drop in for a set or two from the city's top jazz players.
Not so long ago this vibrant museum was the stodgy ol' Chicago Historical Society, which let you cull through thousands of archived photographs and curio. Well, that library still exists, but joining it are several permanent and temporary exhibits, the largest of which is "Chicago: Crossroads of America," a treasure trove of historical objects, including a chunk of the original Fort Dearborn. Other exhibits include “Sensing Chicago” (kids swarm around the giant Chicago hot dog) and revolving displays showing off one of the world's largest costume collections.
Designed by William Le Baron Jenney in the mid-1800s and enhanced several years later by Jens Jensen, Humboldt Park was once the nation’s greatest public park, boasting acres of Prairie-style gardens, grazing animals and a meandering river scene. Though the animals are long gone, the park still offers extensive rose beds as well as tennis courts, an inland beach, baseball fields and bike paths.