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.
This 24.5-acre park might be one of the most popular gathering spots in the city, known for its free concerts, famous public art installations and its proximity to the Loop. The centerpiece of Millennium Park is the Jay Pritzker Pavilion, a flowing Frank Gehry-designed structure that hosts some of the city’s biggest outdoor festivals and concerts. You’ll also find the serene Lurie Garden, al fresco dining destination the Park Grill and pedestrian bridges that lead to the Art Institute and Maggie Daley Park. Welcome to the hub of Chicago’s front yard.
Guarded by an iconic pair of bronze lions, the Art Institute of Chicago houses a permanent collection of more than 300,000 artworks, displayed in a sprawling complex of galleries and halls. You’ll find everything from Japanese prints to ancient Greek sculptures among the pieces housed in the museum’s central galleries, where classic paintings such as Edward Hopper’s Nighthawks and Grant Wood’s American Gothic are also located. For something a bit more contemporary, head for the Modern Wing—a Renzo Piano-designed addition that displays the museum’s architecture and design collection as well as 20th and 21st century art.
Even when the Cubs aren’t playing baseball, there’s plenty to do at this legendary stadium in Wrigleyville. Fans can tour the Friendly Confines, explore the Park at Wrigley, eat and drink the day away from the stands and so much more. Whatever the occasion, there’s no such thing as a boring day at Wrigley Field.
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.
See some 1,200 animals—from apes to zebras to flamingos—at one of the last free zoos in the country. The 35-acre attraction connects visitors with animals from all over the world, and a variety of seasonal events and special programming keep locals coming back again and again.
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.
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.
If you’re looking for breathtaking views of some of Chicago’s most gorgeous architecture, take a stroll along the Riverwalk, which hugs the main branch of the Chicago River and provides a continuous walkway with restaurants, bars and urban attractions at every turn. Clever design features throughout offer areas to lounge around and enjoy the city from a stellar angle.
Housing 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.
Anchoring the aquatic offerings at this Chicago institution are enduring favorites such as piranhas, frogs and snakes of the Amazon; rays, turtles and moray eel of the Caribbean; frightening predator sharks, mesmerizing jellies, adorable penguins and marine mammals like sea lions and otters.
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.
You’ll have to travel to the outermost tip of Museum Campus to visit the Adler Planetarium, but the journey seems appropriate considering this institution’s focus on out of this world experiences. Astronomy and astrophysics take the spotlight at the Adler, which features permanent exhibitions like “Mission Moon,” which documents the history of U.S. space exploration, and “The Universe: A Walk Through Time,” which posits theories on how the galaxy was started. Visitors can also look through the telescope in the Doane Observatory or take in Chicago skyline views outside of the museum on Northerly Island.
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.
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.
Head for the Chicago Cultural Center’s Preston Bradley Hall to see the building’s architectural crown jewel: a stain glass Tiffany dome that’s 38 feet in diameter. Made up of 30,000 individual panes of glass, the dome was renovated in 2008 to allow the dizzying display to once again be lit with natural light. If you’re up for more neck craning, walk to the nearby Grand Army of the Republic Hall, which boasts a neo-classical stained glass dome.
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.
This tourist hot spot features shops, eateries, an IMAX cinema and a bevy of sightseeing boat tours. Pier Park is home to a 200-foot-high Ferris wheel, a beer garden and public art exhibitions galore. You’ll also find the Chicago Children’s Museum, Chicago Shakespeare Theater and a rotating roster of live entertainment on the Family Pavilion Stage. Most offerings may not turn locals on, but the seasonal events, indoor activities and great people-watching provide plenty of entertainment, no matter what the weather.
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.
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.
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.
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