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Rising majestically from the shores of Lake Michigan, Chicago is studded with steely skyscrapers, skirted by beaches and strewn with parks. Though the great American city—“perhaps the last of the great American cities,” wrote novelist Norman Mailer—is the third most populous in the U.S., it boasts its own Midwestern flavor.

The Windy City is approachable, ethnically diverse and proud of both its working-class roots and world-renowned attractions. Explore bold architecture, exceptional museums, a vast restaurant scene and abundance of cultural offerings—from improv comedyto public art to storefront theater—and see for yourself if Chicago is your kind of town. Here’s how to spend three perfect days in the city.

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Day one: Get Loopy

Fuel up at Intelligentsia Coffee in the historic Monadnock Building in the Loop. The well-respected chain, which originated in Chicago, styled this location after an Italian espresso bar with smartly dressed baristas serving up your latte. If it’s a weekday, head to Revival Food Hall for a pastry from Revival Cafe-Bar, or a quick bite to eat from a number of beloved local vendors like Smoque BBQ and Antique Taco. Visiting on a weekend? Have lunch at Latincity, a Latin-inspired food market in Block 37.

Jay Pritzker Pavilion in Millennium Park

Jay Pritzker Pavilion in Millennium Park | Photo courtesy of Monica Pedraja

Next, make your way east to Millennium Park for the obligatoryselfie at Chicago’s most famous public sculpture, The Bean (official name: Cloud Gate), the kid-friendly Maggie Daley Park—accessed via the snakelike BP Pedestrian Bridge—and spectacular views of the skyline. Stroll up the Nichols Bridgeway (pssst…Chicago has a thing for elevated paths and trains), which leads to the Art Institute of Chicago’s Modern Wing. Spend the afternoon exploring the internationally renowned museum—even Ferris Bueller knows this is a must—then grab a mid-afternoon snack and/or drink at the trendy Chicago Athletic Association Hotel. The 1890s building hasbeen stunningly renovated and offers a number of dining and imbibing options—our favorite being Cindy’s, a year-round rooftop cocktail bar that affords an amazing view of Millennium Park and Lake Michigan.

Three Dots and a Dash

Three Dots and a Dash | Flickr CC: Sam Howzit

Make your way north on Michigan Avenue, a.k.a. The Mag Mile, for shopping and sightseeing. A great way to see the city and gain a better appreciation for its impressive buildings—by the likes of Mies van der Rohe, Bertrand Goldberg and Jeanne Gang—is from a boaton the Chicago River. Time permitting, take a Chicago Architecture Foundation River Cruise, followed by a dinner of Chicago-style pizza at Gino’s East Pizza and a cocktail at the Hancock Building’s 96th-floor Signature Lounge. (If deep-dish pizza isn’t your thing, head to the West Loop for dozens more top-notch restaurants, on aptly named Restaurant Row along Randolph Street.) Need a nightcap? Wander to subterranean tiki bar Three Dots and a Dash or the Broken Shaker at the Freehand Chicago, a warm and affordable hostel/hotel in River North.

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Day two: Cultural sampler

Grab a coffee at the Freehand’s Cafe Integral, and then enjoy brunch at Lincoln Park’s lauded Perennial Virant before spending a few hours exploring sprawling Lincoln Park, featuring a conservatory, free zoo and the Peggy Notebaert Nature Museum. Next, drive or Uber up beautiful Lake Shore Drive (or, optionally, rent a Divvy bike and take the Lakeshore Path) and stop at Montrose Beach to experience one of the city’s most scenic and community-oriented beaches. If there’s time, head inland to the Uptown neighborhood, home of the Green Mill, Chicago’s most storied jazz club and a former hangout of Al Capone (pssst…Chicago has a thing for Prohibition-era gangster history).

Green Mill

Green Mill | Flickr CC: BriYYZ

Grab a midday drink (Chicagoans love those), and then either dine on Vietnamese food on Broadway and Argyle—Tank Noodle is one of several worthy options—or head to nearby Andersonville, where you’ll find ample restaurant choices such as Big Jones (coastal Southern fare) and the Hopleaf (Belgian-focused eats and beer). Cap off the night in Old Town with an improv show at famous comedy club Second City, and a post-dinner drink at local dive The Old Town AleHouse, featuring some colorful wall art. Spend the night at the ultramodern Virgin Hotel downtown.

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Day three: Neighborhood finds

Chicago is a city of neighborhoods, so devote your third day to seeing some more of them. Take the Blue Line El train to the always-buzzing Wicker Park for brunch at Dove’s Luncheonette, followed by shopping for…well, anything. Bookstores, record stores and vintage outlets line Milwaukee Avenue, while Damen Avenue is populated by higher-end retail shops like Mark Jacobs and diptyque—though independent Damen boutiques such as Moth and Robin Richman are must-sees for those with eclectic personal style.

Mural in the Logan Square neighborhood

Mural in the Logan Square neighborhood | Flickr CC: Sean Davis

Fans of comics and indie literature will want to wile away the afternoon at Quimby’s, while mid-century modern furniture junkies will feel right at home in Dial M for Modern. Take the El further north to the fast-growing neighborhood of Logan Square, where your dining and drinking possibilities are endless. An always-reliable local option is Lula, featuring artful farm-to-table fare, while Fat Rice offers Southeast Asian-inspired food unlike anything you’ve every tasted before—a must for adventurous eaters. A cocktail at Heavy Feather, a 1970s-style fern bar above the Slippery Slope, will provide a nice coda to the evening. Or maybe it’s just an overture? Logan Square is teeming with bars, after all, if you really want to “drink in” the city.

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Tagged: Midwest

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Laura Pearson

Laura Pearson

Laura is a travel-loving Chicago-based journalist who writes about art and culture. Follow her on Twitter at @tislaurapearson.

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