In one of his most legendary songs, Frank Sinatra immortalized Chicago as “My Kind of Town.” This Midwestern metropolis certainly has become that for countless others. Its cheeky charm and spirited diversity often surprise and delight first-timers to the city. Hop aboard Chicago’s elevated train, affectionately called the “L,” and feel the soft rumble of a train in motion as you weave beneath (and between) downtown skyscrapers and soar above vibrant neighborhood enclaves like Pilsen, Lincoln Park and Wicker Park, where echoes of yesteryear mingle with the diverse stories of today. But don’t just passively observe: Immerse yourself in the goings-on in this city that’s produced hometown heroes such as Oprah, Bill Murray, Michael Jordan, Kanye West and Barack Obama—and it will most certainly surprise and delight you. May these recommendations, which only scratch a surface that runs far deeper than the depths of Chicago’s beloved Lake Michigan, spark your desire to explore and make Chicago “Your Kind of Town.”
LAKE MICHIGAN
This is Chicago’s crowning jewel, a vibrant spot to find active diversions – or a quiet respite from the hustle and bustle of the city.
Lake Michigan often takes out-of-town guests by surprise. Hugged by a soaring city skyline, it dazzles with an ever-changing symphony of blues, greens and purples reflected upon its waters. From the carnival-like grounds of where a 200-foot-tall Ferris wheel offers 360-degree views of the lake and city, you can also book passage on a yacht, sailboat or speedboat for a lake cruise. The Lakefront Path that runs 18 miles up and down the shoreline is a playground for runners, bikers and those simply looking to stroll – with opportunities to stop at the Lincoln Park Zoo, one of the nation’s largest zoos with free admission, or a lakefront museum, like The Shedd Aquarium or The Adler Planetarium, all accessible from the Lakefront Path. The soft-sand beaches sprinkled along this path – from Montrose Beach to North Avenue Beach to Rainbow Beach – transform into a resort-like setting filled with sunbathers, beach volleyball games and the jingling bells of ice cream carts. It’s easy to forget that you’re in Chicago, and not a resort city like Miami. If you plan a summer visit accordingly, you could be a part of the biggest lakefront spectacle of the year: The Chicago Air & Water Show. Held each year since 1959, the free event attracts eyes to the sky as military jets and stunt planes spin high above Lake Michigan. Amidst the lakefront diversions, however, there are plenty of quiet patches of grass and sand upon which to perch, and aimlessly ponder, as the lapping waves of Lake Michigan lull you into a state of calm. Sometimes doing nothing at all in this special setting is, in fact, the best option.
Frontera Grill; Photo Courtesy of Frontera Grill
CULINARY ADVENTURES
Come to Chicago hungry: Choices abound, with some of the best found in its ethnic neighborhood enclaves.
If you think Chicago is strictly a meat-and-potatoes kind of town, think again. The culinary scene is as “evolved” as what you’d find in New York or Los Angeles, with up-and-coming chefs innovating for the palate and farm-to-table feasting proving itself a growing pastime. Chicago is, after all, surrounded by Midwestern farms producing fresh produce, dairy and more. It’s not uncommon to see celebrated chefs like Rick Bayless, whose acclaimed restaurants Frontera and Topolobampo feature some of the hardest-to-get tables, shopping the local farmer’s markets for inspiration. Restaurants concentrated in the River North, West Loop and Lincoln Park neighborhoods provide some sure-fire bets for exciting, and Instagram-able, meals. But, for the truly adventurous, it can be fun to explore the melting pot of cuisine at family-run restaurants in Chicago’s most distinctive cultural neighborhoods. For Indian food, nowhere else in the city holds a candle to the curry dishes you’ll find on Devon Avenue. For amazing Mexican food, head to the Pilsen neighborhood. For soul food and African cuisine, journey to Bronzeville for longstanding spots like Chicago’s House of Chicken and Waffles and Yassa’s (a Sengalese gem). Find hearty Polish delicacies like pierogi, Zurek and paczki whipped up by the world’s largest Polish population outside of Poland in northwest Chicago, especially along Milwaukee Avenue. And for Chinese, head to – you guessed it – Chinatown. It’s kind of like traveling around the culinary world, only you never leave Chicago.
DEEP DISH PIZZA
Discover for yourself which local pizzeria serves up the tastiest version of this Chicago classic.
It’s so synonymous with Chicago, this deserves its own shout out. Deep dish pizza is akin to mother’s milk for many who call the city home. The hearty trifecta of deep crust, layers of cheese and a top layer of tomato sauce is a savory masterpiece that inevitably forces all who enjoy it to loosen their belts. The cheesy calorie-fest, however, doesn’t stop visitors from indulging and plugging into the local debate over who makes the “best” version. The most noteworthy stops on a Chicago pizza tour include Giordano’s, Pizzeria Uno, Gino’s East and Lou Malnati’s, all of which offer multiple locations throughout the city. If you’ve got an iron gut and loose-fitting sweatpants, you could try to hit all four in a single trip. For a unique twist on the classic, hit up Pequod’s, where a signature caramelized crust keeps locals coming back. Deep-dish aside, locals will also point you to some off-the-grid joints that are less frequented by tourists, but are wildly beloved by Chicagoans who prefer to not limit themselves to deep dish and stuffed pies. Vito & Nick’s, a South Side institution since the 1950’s, is a cash-only dive of wood-paneled walls and neon beer signs that will remind you of your grandparents’ retro basement and serves up, arguably, the world’s best pizza: a distinctive thin-crust pizza with cracker-like crust that’s cut into square slices. Whichever you choose, be sure to pair your pizza with one of Chicago’s favored beers: Old Style, PBR or 312.
Architect Frank Lloyd Wright’s home and studio is located in Oak Park.
ARCHITECTURE
Chicago’s architectural eye candy is a fusion of past and present, beautiful to behold but also holding stories of wonder and intrigue for travelers who dig deeper.
Chicago is a city that rose from the ashes – literally. After the Great Fire of 1871 destroyed much of the city, an architectural renaissance emerged that thrives to this day, with up-and-coming designers continuing to add distinctive features to an ever-evolving skyline. Chicago is credited with inventing the skyscraper and its impressive collection is best experienced from the Chicago River aboard an architectural cruise. The Chicago River provides an incredible vantage point: It weaves through downtown Chicago, gliding past towering steel and glass, offering an awesome perspective to ooh, ahh and ogle as knowledgeable docents from the Chicago Architecture Foundation share stories behind the city’s buildings – something you’d likely miss if you were to simply stroll the streets. For a bird’s-eye view, head to the Willis Tower (formerly known as the Sears Tower and still called so by locals) for Skydeck Chicago. Here, you can step into one of the four glass boxes that hover 103 stories in the air for a spine-tingling view of the city’s urban landscape. Back on the ground, walking tours of historic neighborhoods such as Lincoln Park, Bronzeville and Wicker Park will give you an intimate view of grand greystones, beautiful brownstones and vintage mansions once occupied by beer barons, industrial titans and famous artists and activists. For Frank Lloyd Wright enthusiasts, nearby Oak Park is home to the world’s largest collection of buildings designed by legendary “Prairie style” architect, all of which can be explored on a guided bicycle tour. As you explore any of Chicago’s streets, pay attention. Look up and look down, as lots of vintage buildings have been repurposed for today’s use, and something as seemingly simple as an Art Deco detail or chiseled “Schlitz” logo into a building’s façade is a fun discovery that could lead to an even cooler story.
The Goodman Theatre Center on Dearborn Street in The Loop, downtown Chicago.
THEATER
The theater scene is rich and diverse, helping to catapult musicals to Broadway and having groomed future stars such as Tina Fey, Julia Louis-Dreyfus, Keegan-Michael Key and Bill Murray.
Whether you’re into drama, comedy or the totally twisted and experimental – there’s a performance in Chicago to satiate your theatrical appetite. While many visitors venture into the bright lights of the downtown theater district, where ornately-decorated historical theater houses welcome mainstream favorites (“Phantom of the Opera,” “My Fair Lady”) and test-run shows that ultimate land on Broadway (“The Producers,” “The Cher Show”), it’s worth venturing beyond these opulent theaters to explore the true heart of Chicago’s thespian community. Central to its heartbeat include Steppenwolf, Goodman, Lookingglass and Victory Gardens theatres – that’s theatre with an “e,” rather than the pedestrian theater, because they are serious about the craft. Celebrated actors such as William H. Macy, John Malkovich and Laurie Metcalf have graced Chicago’s dramatic stages, so, you could catch a performance staring a future (or current) Oscar winner. On a less serious note, visiting The Second City, Chicago’s legendary improv and sketch comedy theater, puts you in a home that’s produced a treasure trove of comedy legends, including Tina Fey, Steve Carrell, Key & Peele and Bill Murray. Chicago is where improv and sketch comedy was created and cultivated, so coming to this city is like coming to the Holy Land of Comedy, with The Second City being its main church. Other comedic churches at which to pray/laugh would be iO Chicago or The Annoyance Theater, the latter of which is a little darker and rougher around the edges – how else could it pull off shows with titles like “Coed Prison Sluts” and “Holy Fuck Comedy Hour.”
The Famous Blue Chicago Blues Club located on North Clark Street.
MUSIC
Experience a diverse tapestry of music, from iconic blues clubs frequented by living legends to major music festivals that launch the careers of once-obscure indie artists.
There’s a reason entire books are written about the Chicago music scene: It is spectacularly, wonderfully diverse. Blues and jazz, both boasting deep roots in Chicago, are anchored by the melodic and lyrical legacy of legends like Muddy Waters and Louis Armstrong, respectively, both of whom once called Chicago home. Slip into any number of well-worn, dimly-lit music venues to experience it for yourself. For some of the world’s best blues, head to Buddy Guy’s Legends (where the legendary Buddy Guy himself is still known to take the stage), Kingston Mines, B.L.U.E. CHICAGO and Rosa’s Lounge. For jazz, head to Andy’s Jazz Club or The Green Mill, a small Uptown lounge once frequented by Al Capone. If you’re a fan of Chicago House Music, a blend of disco classics and Eurobeat pop first pioneered by underground Chicago DJs, head to the pulsating Smartbar. For Chicago’s only Country Western bar, line dance your way to Carol’s Pub. And for an eclectic assortment of local indie bands, hit up The Hideout, a cozy bar venue rules that’s tucked into an industrial setting and boasts a quirky ambience accented with trophy fishes and Christmas lights. Not all music needs to be experienced indoors, of course. Entire trips can be timed around outdoor music festivals such as Lollapalooza (pop/rock/indie), Pitchfork (indie), Riot Fest (rock/punk/hip-hop) and Country Lake Shake (country), or free events such as the Chicago Blues Festival or Chicago Jazz Festival. Whichever you choose, delectable ear candy awaits.
Cloud Gate also Called "The Bean"; Photo by Gian Lorenzo Ferretti Photography
ART
Beyond Chicago’s most revered museums, a kaleidoscope of public art can be found throughout the city, begging to be admired, questioned, interpreted and made Instagram-famous.
Sure, you could head to one of Chicago’s art museums to satisfy your artistic whimsy. Or you could simply stroll the city streets, where eye-popping public art poke through at almost every corner. More than 500 works of art are sprinkled across the city -- from the water-spitting faces of the Crown Fountain and the selfie-famous Cloud Gate (a.k.a. “The Bean”) at Millennium Park to the sublimely eerie 106 headless and armless iron sculptures of the Agora in Grant Park. As more businesses and schools hire graffiti artists, muralists and mosaic artists to transform the unremarkable into something memorable and meaningful, Chicago further transforms into a living art museum. For instance, Violet Hour, an upscale cocktail lounge in Wicker Park without a sign, features an ever-changing graffiti mural that hides its “secret door,” and several of the underpasses below Lake Shore Drive (accessible from the Lakefront Path) boast handmade mosaics and murals that tell the stories of its neighborhoods. One neighborhood worth strolling for the eye-catching vibrancy of its myriad of murals is Pilsen. Up and down 16th Street, you’ll spot colorful murals by revered local artists JC Rivera and Hebru Brantley, along with a growing collection by international street artists. From the Chicago River to Western Avenue, the walls of an old railroad embankment have been transformed into an evolving outdoor gallery of murals, as well. Of course, Chicago’s collection of art museums hold their own, and if you’re going to visit one, make it The Art Institute of Chicago. It’s a regal downtown fixture home to works by artists known worldwide by single names: Picasso, Monet, van Gogh, Chagall … the list goes on. While there, be sure to spend time in the Thorne Rooms, a beloved collection of pint-sized rooms detailing styles from the 13th century to the 1940s, built on a scale of one inch to one foot, right down to the miniscule textiles and carpets. (If you’re into Tiny houses, this takes that trend to an even teenier and curiously mesmerizing level.) Meander the Art Institute alongside art students, families, tourists and businessmen on break, as many step into the setting for a reprieve and to be inspired – the same could be set for spending time with Chicago’s abundance of public art, too.
Chicago Dog has a Steamed Poppyseed Bun, Fresh Tomatoes, Diced Onions, Neon Green Relish,Peppers,Pickle, Yellow Mustard and a Dash of Celery Salt.
OFFBEAT CHICAGO
The Windy City serves up the wonderfully weird and quirky, especially if you know where to look.
Oregon’s Portland doesn’t have a monopoly on “weird,” as its unofficial slogan might lead you to believe. Find the bizarre, the curious and the wacky alive and well in Chicago. Belly up to the bar early at Big Joe’s, where turtle racing has been a mainstay on Friday nights. Rooting for the fastest slow-moving animal on the track has never been so thrilling, especially when it involves cheap drinks in one of Chicago’s quintessential watering holes. To satisfy late-night hunger (perhaps after watching a few turtle races), head to the Weiner’s Circle for a Chicago style char-dog (no ketchup) and a side of verbal harassment from the famously sassy, profanity-loving cashiers who serve the after-hours crowd, many of whom come simply to participate in the fun tit-for-tat spectacle. (The char-dogs are great, by the way, as is the entertainment that typically ensues at this cash-only hot dog stand after midnight.) Forgo the popular museums for the bizarrely niche ones, such as the Leather Archives & Museum, a surprisingly serious preservation and education of leather, kink, BDSM and fetish lifestyles; the International Museum of Surgical Science, where macabre exhibits include preserved body parts and a vintage iron lung; or the Busy Beaver Button Museum, a small-but-mighty (and free!) museum boasting more than 9,000 historical pin-back buttons. As for tours, why not brag to friends about becoming a Chicago murder expert – the historical kind, of course – with Chicago Crime Tours, a luxury limo bus tour that highlights infamous Chicago crimes and serial killers, or the Untouchable Tours, a two-hour excursion led by costumed “wise guys” that travels to notorious sites of murder and mayhem from the Prohibition era, when Al Capone was the unofficial mayor of Chicago. Continuing with that theme, end your night at The Drifter, a 20s-era speakeasy in the basement of the legendary Green Mill Tavern, where drink menus are presented on tarot cards and magicians and burlesque dancers are among the nightly entertainment.
Michigan Avenue is also known as the Magnificent Mile in Chicago which offers world class shopping; Photo by RiverNorthPhotography
SHOPPING
Indulge in some retail therapy in Chicago’s most beloved shopping districts, where treasures that you didn’t know you needed await.
Considered by some to be the Holy Grail of shopping in Chicago is the famous Magnificent Mile, the northern section of Michigan Avenue that extends through the Gold Coast neighborhood. It’s a bustling window-shopping extravaganza where the people watching can be as much fun as the shopping. Situated between the Shops at Northbridge to the south and Water Tower Place mall to the north, both of which are home to hundreds of stores, sits the world’s largest Starbucks – a massive, three-story temple of caffeine to re-fuel your shopping. When you’re done with the Mag Mile scene, hop a Chicago water taxi, accessible on the southern end of the Magnificent Mile, for Chinatown to explore its eclectic array of shops, some of which are a jam-packed maze of treasures ranging from patterned tea sets to exotic candies to electronic lotus flowers to stacks of fake money -- something certain to fool and entertain folks back home. For a concentrated cluster of one-of-a-kind vintage shops and vinyl stores, the Wicker Park neighborhood is a must. Popular with artists, musicians and the modern indie set, the stretch of Milwaukee Avenue that runs through this neighborhood is where you’ll find mini music meccas such as Reckless Records, Shuga Records and the nearby Dusty Groove, along with some of the city’s coolest vintage apparel shops, such as Store B, Una Mae’s and Vintage Underground. For one of the fanciest – and liveliest – flea markets you’ll ever experience, check out the antiques, fashion, jewelry and global goods for sale at the Randolph Street Market. Held one weekend (Friday-Sunday) each month in Chicago's historic West Loop/Fulton Market district, it’s been named by USA Today as one of the “Top 10 Flea Markets in America.”
Wrigley Field Cubs Hat; Photo by Blake Guidry
SPORTS
Cheer alongside (and trade barbs with) locals in this sports-obsessed town.
Chicago lives and dies by its beloved sports teams. If you thrive on game day adrenaline, this city could be your sports nirvana. It’s the home of Michael Jordan, who led the Chicago Bulls to six NBA Championships, and whose bronze in-flight statue is a popular selfie spot for fans. It’s the home to the Chicago Bears, a football team whose 1985 Super Bowl win is still very much a point of pride amongst fans who occasionally burst out into the classic rap “Super Bowl Shuffle.” It’s the home to a world-champion hockey team, the Blackhawks, and two baseball teams, the White Sox and the Cubs. If you can’t score tickets to a game, you’ll find excitement and camaraderie in neighborhood bars, where celebratory cheers (and groans) echo loudly on game days. Wrigleyville, the center of the Cubs universe, is a particularly colorful neighborhood, even when it’s not a game day. Belly up to the bar at popular spots like the Cubby Bear or Murphy’s Bleachers, or pay a little extra to snag a seat at one of the rooftop bleachers that peek over the outfield for a unique vantage point of games at historic Wrigley Field, the oldest park in the National League. For the South Side flavor, head to Reggies Chicago or Maria’s Packaged Goods and Community Bar and do a few shots of Malort (seriously, we dare you) with locals cheering on crosstown baseball rival, the White Sox. After working up an appetite of participating in Chicago’s frenzied sports enthusiasm, feast at these carnivore-friendly, sports-fan favorites: Ditka’s Restaurant, Harry Caray’s Italian Steakhouse or Michael Jordan’s Steakhouse.
