Whether this is your first time in the Windy City or you’re aching to get beyond the basics, here’s where to go.
The Midwest’s largest city bridges high design and culture with good old-fashioned hospitality—especially come summer when outdoor concerts in Millennium Park, walking tours, boat rides, games at Wrigley Field, and more celebrate the longer days of sunlight. This is not to say that you should rule out wintry days and nights in Chicago because the craft-beer scene, museums like the Art Institute of Chicago and the Field Museum, and comedy institution Second City are great spots to hole up indoors.
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Walk Through Millennium Park
Without a doubt, one of the most popular selfie sites in Chicago at the moment is “the Bean,” a stainless-steel mirrored art sculpture by Anish Kapoor (its official name is “Cloud Gate”). It’s in Millennium Park, a 25-acre public green space filled with art and right on North Michigan Avenue in the Loop. Also in the park is the Frank Gehry-designed Pritzker Pavilion, which hosts free concerts in the summer months; and Crown Fountain, a reflecting pool bookended by two towers that screen video images.
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Expand Your Mind on Museum Campus
Three of Chicago’s most notable museums, all dedicated to the natural sciences, sit inside this 57-acre park on Lake Michigan. At the Field Museum, say hello to Sue, the gigantic T. rex, before immersing yourself in this extraordinary museum’s collection of anthropological and paleontological artifacts and animal dioramas. The dinosaurs are the thing here, but surprising collections of Tibetan Buddhist altars, mummies, and re-creations of famous gems may entice you to linger for hours. The Shedd Aquarium’s fantastically colored fish, as well as dolphins and whales, are completely mesmerizing. Don’t miss the Wild Reef exhibit, where stingrays slide quietly under the Plexiglas at your feet. Taking you on a journey through the stars to unlock the mysteries of our galaxy and beyond, the Adler Planetarium tells amazing stories of space exploration through high-tech exhibits and immersive theater experiences. Interactive elements and real space artifacts bring these fascinating tales of space and its pioneers down to earth.
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Feel Like You're on Top of the World at the Willis Tower Skydeck
Take the ear-popping ride to the 103rd floor of the Willis Tower (née the Sears Tower) to get to Skydeck Chicago, where on a clear day you can see as far as Michigan, Wisconsin, and Indiana. At the top, interactive exhibits feature notable Chicagoans; kids love Knee-High Chicago, a four-foot-high exhibit that has cutouts of Chicago sports, history, and cultural icons at a child’s eye-level. Fearless folks can step out onto the Ledge, twin glass boxes extending 4.3 feet from the Skydeck and suspended a dizzying 1,353 feet above the city. Security is very tight, so figure in a little extra time for your visit.
Shop Till You Drop Along the Magnificent Mile
Exclusive shops, department stores, and boutiques line the northern half of swanky Michigan Avenue, better known as the Magnificent Mile. Even better, the concentration of prestigious stores in vertical malls means you can get a lot of shopping done in winter without venturing into the bluster outside. Originally designed by 19th-century architect Daniel Burnham, this famous section of Michigan Avenue is a potpourri of historic buildings, upscale boutiques, department stores, and posh hotels. Among its jewels are the Tribune Tower, the Wrigley Building, the John Hancock Center, the Drake Hotel, and the Historic Water Tower, one of the few structures that survived the Great Chicago Fire.
Admire World-Class Art at the Art Institute of Chicago
From one of the world’s largest collection of French impressionist paintings (including Claude Monet’s waterlilies and haystacks) to a blockbuster exhibition every year it seems, the Art Institute of Chicago—the country’s second-largest art museum, after the Metropolitan Museum of Art—is a must-not-miss for art lovers. Nearly a decade ago, the Modern Art Wing was unveiled; it now houses the 40-piece collection acquired in 2015 that includes pieces by Andy Warhol, Jeff Koons, Cindy Sherman and Jackson Pollock.
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Sail the Chicago River
There are many ways to get out on the water in downtown Chicago. You could take a boat cruise—and even then, the options range from a narrated 90-minute Chicago Architecture Foundation River Cruise to a two-hour wine and cheese cruise—or rent a kayak or canoe from Wateriders. Not sure how steady you’d be in your own vessel? Book a guided theme tour, such as this two-hour Ghosts and Gangsters tour.
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Have Some First-Rate Laughs at Second City
An institution since 1959, Second City has served as a launching pad for some of the hottest comedians around. Alumni include Dan Aykroyd, Tina Fey, Amy Poehler, and the late John Belushi. It’s the anchor of Chicago improv. The revues on the company’s main stage and in its smaller e.t.c. space next door are actually sketch comedy shows, but the scripts in these pre-rehearsed scenes have been developed through improvisation and there’s usually a little time set aside in each show for the performers to demonstrate their quick wit. Most nights there is a free improv set after the late show, featuring cast members and invited guests (sometimes famous, sometimes not, never announced in advance). It’s in Donny’s Skybox upstairs that you’re more likely to see one of Chicago’s many fledgling improv comedy troupes making their first appearance working together on freshly penned material in public.
Cheer on the 2016 World Series Champions Chicago Cubs at Wrigley Field
The Cubbies have always been a draw but even more so now after their historic World Series win in 2016. Wrigley Field—built in 1914—is in the heart of Chicago’s Wrigleyville neighborhood, a section of the city teeming with new entertainment and lodging, including the new Hotel Zachary, a boutique hotel with 12 restaurants and bars (even a Jeni’s scoop shop), perfect for bunking down during a series.
See a Shakespeare Play at Navy Pier
To avoid the tourist traps at Navy Pier—but still say you’ve been there, because it really is neat to be on a pier that juts out into Lake Michigan—get tickets to the Chicago Shakespeare Theater. Performances are at the pier. Last year the theater unveiled The Yard at Chicago Shakespeare, an additional performing-arts space and also at the pier. Traveling to Chicago during the summer? Chicago Shakespeare in the Park hosts pop-up productions around the city.
See the Animals at Lincoln Park Zoo
At this urban enclave near Lake Michigan, you can face off with lions outside the Kovler Lion House, watch about two dozen gorillas and chimpanzees in the sprawling Regenstein Center for African Apes, and see animals both slithery (pythons) and strange (sloths) in the glass-dome Regenstein Small Mammal and Reptile House. Inside the Lincoln Park Zoo, the big guys (hippos, giraffes, and black rhinos) are in the Regenstein Animal Journey, and bird lovers should make a beeline to the McCormick Bird House, containing extremely rare birds, some of which are extinct in the wild. The children’s zoo, Farm-in-the-Zoo (farm animals and a learning center with films and demonstrations), and LPZoo Children’s Train Ride appeal to youngsters.
Hang on the Oak Street Beach
Chicago is rarely associated with “beach days,” as might be the case in Santa Monica or Miami, but that’s a secret only locals know. And these are not just stretches of sand. You can sit down to a quality meal at the beach, too, including Oak Street Beach at Oak Street Beach and Shore Club at North Avenue Beach, with its whitewashed interior and bed-sized chaises.
Take in the View Over Drinks at the Signature Room
Here’s a tip about getting the best view (for a great price) at the former John Hancock Center (as of early 2018, now called 360 Chicago) along the Mag Mile on North Michigan Avenue. Skip the expensive entrance fee ($21) to this 100-story marvel for a cocktail on the skyscraper’s 96th floor, where your money goes toward supporting either a local craft brewer or a creative mixologist via a beer or cocktail ($10-$17.50) at the Signature Lounge at the 96th.
STAY: The Willows Hotel
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Sample Deep-Dish Pizza at Pequod’s
You likely already know that Chi-town’s signature pizza style is super-thick, composed of layers of sauce and cheese. And if that’s not indulgent enough for you, opt for a stuffed version. But don’t go where tourists eat (Giordano’s, Lou Malnati’s, Pizzeria Uno or Gino’s East—cue long wait times). Stray off the path to a locals’ favorite, like Pequod’s, with a location in Lincoln Park and another in Morton Grove (a suburb). The weekday lunch special runs a rock-bottom $4.95.
Listen to Live Jazz and Blues
Chicago’s rep as a jazz and blues destination hasn’t hit a bad note–ever. Today you can listen to live jazz at Green Mill any night of the week (on the North Side) or head to blues legend Buddy Guy’s namesake club (Buddy Guy’s Legends) firmly planted in the South Loop since 1989. In town during the summer? Check out the Chicago Blues Festival in Millennium Park, held in early June and the largest free blues festival in the world.
Celebrating the city’s Hispanic heritage in many ways, Pilsen (West of the Loop) includes the National Museum of Mexican Art (offering free admission) and a myriad of Mexican eateries, including 5 Rabinitos, with a Rick Bayless protégé at the helm. Don’t leave the area without admiring the artist-created murals along 16th and 18th streets.
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President Obama’s former stomping grounds are worth some space in your Chicago itinerary. This handsome neighborhood is home to the incredible Museum of Science and Industry; the scenic, man-made peninsula called Promontory Point; Frank Lloyd Wright’s Robie House; and the Gothic-style campus of the University of Chicago.
Have Drinks in Logan Square
One of the city’s hippest corners is Logan Square, where you can have a fun night out eating and drinking at some of the neighborhood’s buzziest spots. Start with dinner at beloved Lula Cafe, and then stop into Revolution Brewing for craft beers. Afterward, hit atmospheric cocktail dens like Longman & Eagle or Billy Sunday.
Wander Through the Chicago Cultural Center
Totally free to enter, this stunningly beautiful building in the Loop dating back to 1897 celebrates all types of art, from Chamber Mondays (jazz and strings music the 1st and 4th Mondays of the month) to rotating art exhibits. Be sure to look up and view the world’s largest Tiffany stained-glass dome, fresh off a 2008 restoration.
Tour Frank Lloyd Wright-Designed Properties
Illinois’ most famous architect—Frank Lloyd Wright—is widely known for the Prairie style of architecture he spawned. While most people have been to his birthplace (the suburb of Oak Park), you can also tour a home he designed in the city proper.
Emil Bach House, on Chicago’s North Side, even takes overnight reservations for the ultimate deep dive into Wright’s work; otherwise, tour on Tuesday and Wednesday afternoons from May through September.
Dine on Dim-Sum in Chinatown
The perfect lazy Saturday or Sunday in Chicago? Brunching on dim-sum in Chinatown.
Dolo Chicago is a rare Chinatown restaurant with a full bar (sweet!) and classy décor (think walls back-lit in purple, sleek light fixtures and half-moon-shaped booths). Come summer, the patio is open. Pro tip: Limited on time or desperate to tick off a visit to one of Chicago’s Top Chefs? Stephanie Izard’s Duck Duck Goat serves dim sum on Saturdays and Sundays only; it’s in the Fulton Market District.
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Bicycle or Walk the 606
Similar to New York City’s High Line, this abandoned elevated rail line—open since 2015—is now a fun place to walk and take in art all at once. The edgy, splashy and bright murals are depicted along the 2.7-mile route, which you can access by hopping on the CTA’s Blue Line and getting off at the Western or Damen stops. Ahead of your visit, check out this interactive map for further orientation. The route runs through the Wicker Park, Humboldt Park, Bucktown and Logan Square neighborhoods.
Visit the Museum of Contemporary Art Chicago
Tucked into the tony Gold Coast neighborhood, the Museum of Contemporary Art Chicago—a younger (and considerably smaller, not to mention more provocative) cousin of the Art Institute of Chicago—specializes in contemporary art, whether it’s the permanent collection (featuring such notable artists as Francis Bacon, Alexander Calder and Andy Warhol) or a rotating show. In 2017, Marisol debuted, where the interior mirrors the museum’s modern-art collection and inventive items (like fried quail and miso-butterscotch pudding) are served for brunch, lunch and dinner are served; chef Jason Hammel is widely known in Chicago for his other eatery, Lula Café.
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Take in the View From a Rooftop Bar at the J. Parker
Within the last five years, the number of rooftop bars in Chicago has exploded—and they’re not just downtown. The J. Parker on top of Hotel Lincoln boasts a stunning view of Lincoln Park while Raised’s view is that of the Chicago River from its perch on Wacker Drive. Both serve foodie-approved cocktails and snacks, are open year-round, and are high on design—for example, Raised turned greenhouse structures into chic cabanas.
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Sample Chicago's Craft Beer at Half Acre
Up until recently Goose Island Beer Co. was considered the dominant player in Chicago’s craft-beer scene. Now, however, there are many suds producers, to the tune of 200 or so. Half Acre Beer’s tap room in Lincoln Park—also home to the brewery—is suited for gourmands with a food menu of unique burritos such as pineapple pork fried rice; or a vegetarian one with wheat berries, beets, spinach and goat cheese. About a dozen beers are always on tap.
Smell the Flowers at Garfield Park Conservatory
This conservatory on the west side of Chicago in Garfield Park—and on the National Register of Historic Places—is a big hit no matter what the season is, thanks to two inside acres, but come summer the surrounding 12 acres of outdoor gardens are in bloom. Periodic events include free yoga classes and the Music Under Glass series. Admission is free. Plug into the digital tour guide via your smartphone or tablet to learn even more about the conservatory’s flora during a visit.
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