© Ryan Arnst

Chicago

Steely skyscrapers, top chefs, rocking festivals – the Windy City will blow you away with its low-key cultured awesomeness.

Art & Architecture

It's hard to know what to gawk at first. High-flying architecture is everywhere, from the stratospheric, glass-floored Willis Tower to Frank Gehry's swooping silver Pritzker Pavilion to Frank Lloyd Wright's stained-glass Robie House. Whimsical public art studs the streets; you might be walking along and wham, there's an abstract Picasso statue that's not only cool to look at, but you're allowed to go right up and climb on it. For art museums, take your pick: impressionist masterpieces at the massive Art Institute, psychedelic paintings at the midsized Museum of Mexican Art or outsider drawings at the small Intuit gallery.

Chowhounds' Delight

Loosen your belt – you've got a lot of eating to do. On the menu: peanut-butter-and-banana-topped waffles for breakfast (at Stephanie Izard's Little Goat), pork-shoulder posole and garlicky yucca enchiladas for lunch (at Dove's Luncheonette) and fine dining on foraged foods for dinner (at Iliana Regan's Elizabeth). You can also chow down on a superb range of global eats from Vietnamese pho to Mexican carnitas, Polish pierogi and Macanese fat rice. Still hungry? Order a late-night deep-dish pizza or seek out a hot and spicy Italian beef sandwich at a local fast-food joint.

Sports Fanatics

Chicago is a maniacal sports town, with a pro team for every season (two teams, in baseball's case). Watching a game is a local rite of passage, whether you slather on the blue-and-orange body paint for a Bears football game, join the raucous baseball crowd in Wrigley Field's bleachers, or plop down on a bar stool at the neighborhood tavern for whatever match is on TV. Count on making lots of spirited new friends. Should the excitement rub off and inspire you to get active yourself, the city's 26 beaches and 580 parks offer a huge array of play options.

Rollicking Festivals

Chicago knows how to rock a festival. Between March and September it throws around 200 shindigs. The specialty is music. Blues Fest brings half a million people to Millennium Park to hear guitar notes slide and bass lines roll, all for free. During the four-day Lollapalooza megaparty, rock bands thrash while the audience dances in an arm-flailing frenzy. Smaller, barbecue-scented street fests take place in the neighborhoods each weekend – though some rival downtown for star power on their stages (oh, hey, Olivia Newton-John at Northalsted Market Days).

Planning Toolkit

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  • Plan a day trip full of local flavor and get back in time with these same-day options.

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  • Ways to maximize the fun without spending a dime on your next great adventure.

Top attractions

These are our favorite local haunts, touristy spots, and hidden gems throughout Chicago.

  • Stadium

    Wrigley Field

    Built in 1914, Wrigley Field – aka the Friendly Confines – is the second-oldest baseball park in the major leagues. It’s home to the Chicago Cubs and filled with legendary traditions and curses, including a team that didn't win a championship for 108 years. But a World Series victory coupled with heaps of new family-friendly and foodie hot spots around the stadium have given it new life. The ballpark provides an old-school slice of Americana, with a hand-turned scoreboard, ivy-covered outfield walls and an iconic neon sign over the front entrance. Billy Goat: the curse of Wrigley Field The curse started with Billy Sianis, owner of the Billy Goat Tavern. The year was 1945 and the Cubs were in the World Series against the Detroit Tigers. When Sianis tried to enter Wrigley Field with his pet goat to see the game, ballpark staff refused, saying the goat stank. Sianis threw up his arms and called down a mighty hex, saying that the Cubs would never win another World Series. Years rolled by, and they didn’t. Then in 2016 it happened: the Cubs won the Series in a wild, come-from-behind set of games. The young team scrapped, slugged and pitched its way to victory, exorcising the curse. The city went insane. Streets filled with revelers. Neighbors high-fived neighbors. Grandparents cheered with grandkids. At the victory parade a few days later, an estimated five million fans partied with the team. Wrigley Field traditions When the middle of the seventh inning arrives, it's time for the seventh inning stretch. At Wrigley Field, you stand up for the group sing-along of "Take Me Out to the Ballgame," often led by a guest celebrity along the lines of Mr T, Ozzy Osbourne or the local weather reporter. Here's another tradition: if you catch a home run slugged by the competition, you’re honor-bound to throw it back onto the field. After every game the ballpark hoists a flag atop the scoreboard. A white flag with a blue "W" indicates a victory; a blue flag with a white "L" means a loss. Wrigley Field statues Statues of Cubs heroes ring the stadium. Ernie Banks, aka "Mr Cub," stands near the main entrance on Clark Street; the shortstop/first baseman was the team’s first African American player. Billy "Sweet-Swinging" Williams wields his mighty bat by the right field gate on Addison Street at Sheffield Avenue. Adored third baseman Ron Santo makes a smooth catch beside him. And mythic TV sportscaster Harry Caray dons his barrel-sized eyeglasses in front of the bleacher entrance on Waveland Avenue. Caray was known for broadcasting among the raucous bleacher fans while downing a few beers himself. It’s said the sculptors mixed a dash of his favorite beer in with the white bronze used for the statue. Cubs tickets and stadium tours Buy tickets at the Cubs' website or Wrigley box office. Online ticket broker StubHub is also reliable. The Upper Reserved Infield seats are usually pretty cheap. They're high up, but have decent views. Ninety-minute stadium tours are available most days April through September. Try going on a non-game day, as you'll see more. Gallagher Way The field is uniquely situated smack in the middle of a neighborhood, surrounded on all sides by houses, bars and restaurants. The grassy plaza just north of the main entrance – aka Gallagher Way – has tables, chairs, a coffee shop and a huge video screen. On nongame days it's open to the public and hosts free movie nights, concerts and alfresco fitness classes; on game days it's a beer garden for ticket holders. Kids love the grassy expanse, where they can run around, play catch or cool off in the splash pad. A slew of new cocktail bars, beer bars and hip taco, barbecue and fried-chicken eateries beckon across the way on Clark and Addison Streets.

  • Museum

    Museum of Science & Industry

    The MSI is the largest science museum in the Western hemisphere and a place to completely geek out. Highlights include a WWII German U-boat nestled in an underground display, the life-size shaft of a coal mine, and the "Science Storms" exhibit with a mock tornado and tsunami. The museum's main building served as the Palace of Fine Arts at the landmark 1893 World’s Expo, which was set in the surrounding Jackson Park. Here are some of the museum's best bits, level by level. Level 1 Level 1 holds the U-boat, which is incredibly impressive. It's given the Hollywood treatment with blue spotlights moving over it and dramatic music swelling in the background. An interactive kiosk lets you try to break codes. There's plenty more to see around the sub, but the highlight is going on board and touring the cramped quarters. The Space Center with rockets and the Apollo 8 lunar module, the 'fairy castle' dollhouse and the Farm Tech exhibit with huge tractors to climb are other Level 1 highlights. Level 2 Level 2 rolls out lots of trains. Science Storms lets you conjure a mock tornado and simulate a tsunami rolling toward you. Or submerge into the realistic shaft of a coal mine (temporarily closed). Level 3 Level 3 hangs cool old German dive bombers and English Spitfires from the ceiling."You! The Experience" has a giant 3D heart to walk through and the infamous body slices (cadavers displayed in half-inch-thick pieces) that have been scaring kids for decades. Tickets and other practicalities Tickets include access to most permanent exhibits and selected temporary exhibitions, and should be booked online in advance. There are ramps and elevators allowing for wheelchair access throughout the museum. Top tips for visiting the museum In summer and during popular exhibits lines can be long. The museum is vast, so get a map at the desk and make a plan of attack to see your top exhibits. Little kids (aged 10 and under) get stoked for the hands-on Idea Factory on Level 1; big kids get stoked for the flight simulators on Level 3.

  • Museum

    Art Institute of Chicago

    The second-largest art museum in the country, the Art Institute houses a treasure trove from around the globe. The collection of impressionist and postimpressionist paintings is second only to those in France, and the number of surrealist works is tremendous. Wander the endless marble and glass corridors, and rooms stuffed with Japanese prints, Grecian urns, suits of armor, Grant Wood's American Gothic, Edward Hopper's Nighthawks and Georges Seurat's A Sunday Afternoon on the Island of La Grande Jatte. The Modern Wing dazzles with Picassos and Mirós. Audio guides Download the free app for DIY audio tours; it offers several quick-hit jaunts, from highlights to architecture and pop-art tours. Allow two hours to browse the must-sees; art buffs should allocate much longer. Tickets and other practicalities Tickets should be bought online in advance of your visit. Children under 14 can visit for free. Wheelchairs are available on a first-come first-serve basis. There are several accessible parking garages near the Art Institute. The main entrance is on Michigan Ave, but you can also enter via the dazzling Modern Wing on Monroe Street. Ask at the front desk about free talks and tours once you're inside. Note that the 3rd-floor contemporary sculpture terrace is always free. It has great city views and connects to Millennium Park via the mod, pedestrian-only Nichols Bridgeway.

  • Park

    Millennium Park

    There's free admission to Millennium Park, the playful heart of the city. It shines with whimsical public art, both permanent and temporary exhibits, and it hosts a mixture of free and ticketed activities and events. From the band shell to the artworks on display, here are the top things to see in Millennium Park. Pritzker Pavilion Pritzker Pavilion is Millennium Park's acoustically awesome band shell. Architect Frank Gehry designed it and gave it his trademark swooping silver exterior. The pavilion hosts free concerts at 6pm on Mondays and Thursdays from August to September. Take an evening picnic along and enjoy the sounds from a spot on the Great Lawn. Cloud Gate sculpture in Millennium Park is also know as "the Bean" © roman_slavik / Shutterstock" data-embed-button="images" data-entity-embed-display="media_image" data-entity-embed-display-settings="{"image_style":"","image_link":""}" data-entity-type="media" data-entity-uuid="39769f1b-a62a-4b38-b319-5fee1a890701" data-langcode="en" title="Cloud Gate in Millennium Park at Sunrise, Chicago"> The Bean Cloud Gate, Anish Kapoor's beloved silver sculpture in Millennium Park, is known informally as "the Bean." It reflects both the sky and the skyline, and everyone clamors to walk under it, take a picture and to touch the smoothness of its highly polished stainless-steel exterior. Crown Fountain Jaume Plensa’s two 50ft-high glass-block towers contain video displays that flash a thousand different faces of locals. Each mug puckers up and spurts water, just like the gargoyles atop Notre Dame Cathedral. A fresh set of non-puckering faces appears in winter, when the fountain is dry. On hot days the fountain crowds with locals splashing around to cool off. Kids especially love it. Lurie Garden If the crowds at the Bean, Crown Fountain and Pritzker Pavilion are too much, seek out the peaceful Lurie Garden, which uses native plants to form a botanical tribute to Illinois’ tallgrass prairie. Visitors often miss it because it's hidden behind a big hedge. Yellow coneflowers, poet's daffodils, bluebells and other gorgeous blooms carpet the 5-acre oasis; everything is raised sustainably and without chemicals. A little river runs through it, where folks kick off their shoes and dangle their feet. McCormick Tribune Ice Rink In winter time, Chicago's largest outdoor ice rink opens at McCormick Tribune Plaza and fills with skaters. It's free to skate; you just need to pay for skate rental. BP Bridge Frank Gehry designed the snaking pedestrian BP Bridge that spans Columbus Drive. The luminous sheet-metal walkway connects Millennium Park from the back of the Great Lawn to Maggie Daley Park. The bridge offers great skyline views, too. Nichols Bridgeway Renzo Piano designed Nichols Bridgeway, a silver, pedestrian-only span. It arches from Millennium Park over Monroe Street to the Art Institute’s small, 3rd-floor sculpture terrace (which is free to view). Piano, incidentally, also designed the museum's Modern Wing, which is where the sculpture garden is located. Free exercise classes A schedule of free yoga, Pilates, Tai Chi and Zumba classes take place Saturday mornings in summer on the Great Lawn.

  • Tower

    Willis Tower

    Willis Tower is Chicago's tallest building (and one of the world's loftiest). Breathe deeply during the ear-popping, 70-second elevator ride to the 103rd-floor Skydeck, then stride to one of the glass-enclosed ledges that jut out in midair for a knee-buckling perspective straight down some 1400ft. A bit of history: it was the Sears Tower from its completion in 1973 until insurance broker Willis Group Holdings bought the naming rights in 2009. The building held the title of world's tallest building for almost a quarter century, surpassed by NYC's One World Trade Center in 2013. Tickets and other information Tickets are timed and should be purchased online in advance of your visit. The Skydeck is fully wheelchair-accessible, with complimentary wheelchairs available on a first-come, first-served basis. There are specific facilities for family travelers too, with quizzes and games for children. The entrance is on Jackson Blvd. Even with pre-booking, lines can take up to an hour on busy days (peak times are in summer, between 11am and 4pm Friday through Sunday, although some say sunset is the best time to visit).

  • Museum

    Field Museum of Natural History

    The Field Museum houses some 30 million artifacts and includes everything but the kitchen sink – beetles, mummies, gemstones, Bushman the stuffed ape – all tended by a slew of PhD-wielding scientists, as the Field remains an active research institution. The collection's rock star is Sue, the largest Tyrannosaurus rex yet discovered. She even gets her own gift shop. Special exhibits, such as the 3-D movie, cost extra.

  • Park

    Northerly Island

    This hilly, prairie-grassed park has a walking and cycling trail, bird-watching, fishing and an outdoor venue for big-name concerts. It's actually a peninsula, not an island, but the Chicago skyline views are tremendous no matter what you call it. Stop in at the field house, if it's open, for tour information. Bicycles are available at the Divvy bike-share station by the Adler Planetarium. Note that parts of the trail are closed at times due to weather damage.

  • Waterfront

    Navy Pier

    Half-mile-long Navy Pier is one of Chicago's most-visited attractions, sporting a 196ft Ferris wheel and other carnival rides ($9 to $18 each), an IMAX theater, a beer garden and lots of chain restaurants. A renovation added public plazas, performance spaces and free cultural programming. Locals still groan over its commercialization, but its lakefront view and cool breezes can't be beat. The fireworks displays on summer Wednesdays (9:30pm) and Saturdays (10:15pm) are a treat too.

  • Architecture

    Rookery

    The famed firm of Burnham and Root built the Rookery – named for the site's previous building, a temporary city hall that was popular with roosting pigeons – in 1888; Frank Lloyd Wright remodeled the two-story lobby atrium 19 years later. It's renowned for its contrast in styles: though it may look hulking and fortress-like outside, it’s light and airy inside. You can walk in and look around for free. Tours ($10 to $15) are available weekdays at 11am, noon and 1pm.

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