The Bean. Willis Tower. Wrigleyville. The Metropolis of the Midwest has a lot to offer for tourists. But what about the local Chicago experience? The authentic Chicago. We’re talking about the restaurants, bars and activities that will give you a true local experience.
To welcome you to the Second City—and History Factory’s third—we’ve put together a list of our favorite local spots and, of course, the best Chicago deep dish. Welcome to the authentic Chicago!

 

The Best Deep Dish in Chicago. There, We Said It!

 

  • Lou Malnati’s: Many Chicagoans prefer the thin crust, leaving the tourists to stand in line for hours to gorge themselves on the deep-dish stuff. Lou’s caters to both tastes and is better than the Giordano’s, Gino’s and Uno’s of this world.

 

Watering Holes

 

  • Gilt Bar: Dark and intimate, with a terrific selection of cocktails expertly poured by some of the finest bartenders in Chicago.

 

  • The Old Town Ale House: Cash-only dive bar right near The Second City comedy club. The walls have paintings by the owner, Bruce Elliott, including the infamous naked Sarah Palin holding an assault rifle. In short, it’s a neighborhood tavern with a side of sass. Featured on the late Anthony Bourdain’s show Parts Unknown.

 

  • Green Mill Cocktail Lounge: A former speakeasy with period décor that was once owned by Al Capone’s crew. Dance the night away, every night: It’s open until 4 a.m.

 

  • B.L.U.E.S.: Chicago is synonymous with a few things: pizza, hot dogs, sports, and last but not least, the blues. The Chicago B.L.U.E.S. bar, across the street from the much more famous (and touristy) Kingston Mines, is a dimly lit spot that is as authentic as it gets. Routinely voted as “the best on the North Side,” this divey bar pumps out music seven nights a week.

 

  • Zakopane: A Wicker Park staple since before the hipsters invaded. This bar, named after the Polish region of origin of its owners, is cash only. With only one beer on tap—Budweiser (sometimes stale), this is the dive bar of dive bars.

 

Cuisine

 

  • Weiner Circle: The employees, who are famous for hurling insults at patrons, are as tongue-in-cheek as the establishment’s name. Grab a famed Chicago dog with all the fixings—relish, a pickle spear, tomatoes, sport peppers, onions, celery salt and yellow mustard. Just don’t ask for ketchup.

 

  • MingHin: For amazing dim sum, take the water taxi down the Chicago River to Chinatown, where you’ll find MingHin, recognized by the Michelin Guide as a Bib Gourmand restaurant.

 

  • Manny’s Deli: Imagine a corned beef on rye piled fresh, hot and so high you can hardly wrap your mouth around it. Grab a tray, make your picks and get in line at this institution on Roosevelt Road, south of the Loop.

 

  • Mia Francesca: This Italian restaurant serves classic fare in a boisterous setting. The Lakeview branch is particularly handy if you’re headed to a Cubs game in the summer, but book ahead.

 

  • 90 Miles Cuban Cafe: Featured on Diners, Drive–Ins and Dives, the Bucktown/Logan Square location feels like stepping into Havana. The enclosed porch is home to weekly flamenco shows and other live entertainment. BYOB.

 

  • The Original Mr. Beef: Since 1963, Mr. Beef has been cooking up authentic Chicago beef sandwiches for the public. It’s a must, but don’t wear a white shirt. You’ll thank us later.

 

Authentic Pit Stops

 

  • Wicker Park/Bucktown: Consider it the Brooklyn of Chicago. Funky thrift stores, an already established culinary scene and great bars–anything from divey neighborhood joints to upscale cocktail bars serving house-made ingredients and infused liquors.

 

  • The Bloomingdale Trail (606): The New York High Line’s little cousin. This previously elevated industrial railroad was vacant for many years until it was converted into a running trail/park on the same height as the EL.

 

  • The Prairie District: This neighborhood, situated between State Street and LSD (Lake Shore Drive) on the South Side, is host to some seriously impressive historic homes. After the Great Chicago Fire, this was the neighborhood to live in.

 

  • Montrose Beach: Sure, Chicago winters are terrible, but the summers are what keep us here. Instead of heading to some of the more touristy beaches at North Avenue and Oak Street, head up north to Montrose or Foster Avenue. Bonus points for bringing four-legged friends—Montrose is home to the city’s best dog beach.

 

  • Randolph Street Market: Randolph Street Market and Fulton Market are home to new world-class and innovative restaurants housed in old meat-packing warehouses. With huge renovations under way, these districts are also home to offices for McDonald’s and Google.

 

  • Ravenswood: This tree-lined neighborhood on the North Side is home to Chicago’s best artisans. With great little boutiques and workshops dotting the neighborhood, it’s easy to spend an afternoon wandering around admiring the wares. It’s also easy to spend an afternoon on “Malt Row,” home to some of Chicago’s best breweries: Half Acre, Begyle, Dovetail, and Band of Bohemia (the first brewpub to earn a Michelin Star).

 

Must-Dos

 

  • Jeppson’s Malört: Get the newbie to take one. It’s gross, but it’s a Chicago tradition. Pair it with an Old Style for a Chicago Handshake—our version of a boilermaker.

 

  • Outdoor concerts at Ravinia and Millennium Park: Chicago goes outside in the summer to hear famous artists in its most beautiful parks. Ravinia has a packed calendar in the summer: Bring a picnic basket and listen to the Beach Boys, Jethro Tull, The Who and more. Millennium Park hosts weekly concerts and movie nights. The Pritzker Pavilion is right next to the famous Cloud Gate (known to locals simply as “The Bean”).

 

  • Chicago Architecture Center’s Open House Chicago: Once a year, some of Chicago’s most iconic, unique and beautiful buildings that are otherwise off limits open their doors to the public. It’s your chance to explore neighborhoods and get some culture at the same time.

 

  • Chicago Water Taxi: You could take one of the touristy boat tours and pay $40 for an hour—or hop on the water taxi and ride like a local. You won’t get the vaguely accurate historical narration from a high school student on summer vacation, but unlimited day passes are only $9. Alternatively, take the architectural tour if you do want to do the touristy thing—even for locals, it’s a good history lesson.

 

  • Starved Rock State Park and Mathiessen State Park: Chicago’s sprawling suburbs don’t have much in the way of nature. A couple of hours south of the city are Starved Rock and Mathiessen state parks, with a host of trails and waterfalls. On the way back, you’ll pass Jamie’s Outpost Parlor, filled with eclectic wares and great (and I mean great) people-watching. Grab a well-earned cold beer on the deck after a day’s hike.

 

  • The Lakefront Trail: Ride your bike from Evanston to the Museum of Science and Industry in Hyde Park (take a spin past Obama’s former home). This 21-plus-mile bike ride stretches almost the entirety of the city. Admire the beach and Lake Michigan to your left (you’ll swear it’s an ocean the first time you see it) and the skyline to your right. Just watch out for pedestrians.

 

  • Lincoln Park Zoo: Polar bears, penguins, lions and rhinos… for free? Yes, in Chicago’s Lincoln Park, there’s a free zoo. A personal favorite is the monkey house, where you can find chimpanzees and gorillas—they really are just like us! During the holidays, the zoo hosts Zoo Lights, where you can see the animals by the glow of Christmas lights.

 

  • Art First Friday at Pilsen: The first Friday of every month, local artists in Pilsen, Chicago’s traditionally Mexican neighborhood, open their studios (and often apartments) to the public for free. Pop in and out of the galleries on Chicago’s biggest art day of the month (wine and cheese mandatory).

 

  • Garfield Park Conservatory: Situated west of the city, this conservatory is an oasis. With multiple massive greenhouses, including desert, palms and fern houses, this botanic garden is a nice getaway from the hustle and bustle.

 

  • Shedd Aquarium: The view from the Shedd at night might be the best view of Chicago’s skyline. See the dolphins at night (if you dare) by walking through the bushes and up to the glass atrium behind the museum.

 

  • The Original Rainbow Cone: Do you love ice cream? Are you indecisive? You’ll love Rainbow Cone. Here you can get chocolate, strawberry, Palmer House (New York Vanilla with cherries and walnuts), pistachio and orange sherbet.
Share this

More on this Topic