10 ways to fit in like a true Chicagoan

Despite its rank as the third most populous city in the country, Chicago is often underestimated and misunderstood, say residents.

When non-Chicagoans think of the Windy City, they might imagine freezing winters and thick accents gushing with love for “da Bears.” However, visitors and new residents can more often find friendly neighbors, an eclectic mix of cultures, and world-class food and architecture.

“Everyone is so blown away that people [here] are just kind. They think of big-city mentality and people hustling, pushing you out of the way and grabbing cars — that’s just not our reality,” said agent Jim Abbott of Baird & Warner, a lifelong Chicagoan. “I like Chicago because it has all the culture of New York, but it has that Midwest friendliness. Everything is a little more low key. There’s not a lot of pomp and circumstance anywhere in Chicago.”

The heart and soul of the city can be found across its 77 community areas — and it has hundreds more unofficial neighborhoods.

“We really live and play in our neighborhoods,” said Jason Lesniewicz, senior director of cultural tourism at Choose Chicago, the city’s tourism bureau. “We go downtown for the museums or the theater or big events, but we really truly support our neighborhoods.”

It helps to know which one of these areas you’re in, whether it’s the West Town neighborhood, its Ukrainian Village enclave, or on the South Side, Back of the Yards within the larger New City.

“Our neighborhoods we take very seriously,” said Abbott. “Do know your neighborhood and certainly talk to people in your neighborhood.”

Many of the city’s neighborhoods are based around cultures where a predominant ethnicity of people reside or resided in the past, such as Greektown, Little Italy, Pilsen, Little India, Chinatown, Humboldt Park, and more, often just a mile between one another. Each neighborhood offers its own authentic cuisines, festivals and events, museums, and other art and cultural offerings.

Chicago offers major institutions like the Griffin Museum of Science and Industry, Shedd Aquarium, Field Museum, Adler Planetarium, Museum of Contemporary Art, the Natural History Museum, and the Art Institute of Chicago. These can be tourist attractions, but residents still visit the major museums often as they change exhibits.

State and city residents receive free admission to the city’s museums on specific days ,and library cards grant free admission. Museums can be found throughout the city within the many neighborhoods. Lesniewicz estimates the city has more than 50 museums.

“Our neighborhoods are filled with great museums from the National Museum of Mexican Art to the National Museum of Puerto Rican Arts and Culture, and the Southside Community Art Center, and the Intuit Art Museum, and Ukrainian National Museum — you have all these great cultural enclaves that hold onto their culture here, and they’re celebrated in some of these museums across the city,” said Lesniewicz.

Call the iconic Chicago building at 233 South Wacker Drive Willis Tower, and Chicagoans will know you’re from out of town. Though the skyscraper, once the tallest in the world, changed names in 2009 to Willis Tower, it will always be Sears Tower to Chicagoans.

The same goes for the stadium the White Sox play in (Comiskey Park, but currently Rate Field) and one of the largest downtown department stores (once Marshall Field’s, but now Macy’s).

“Comiskey Park will always be Comiskey Park even if it was changed,” said agent Erika Villegas of RE/Max in The Village and current president of the Chicago Association of Realtors. “For sure, that’s never going to go away. We call it what we’ve always called it or the way we knew it as a kid.”

Many visitors and new residents can be surprised by the vibrant food scene in Chicago. It’s a city with much more than pizza, Chicago-style hot dogs, and Italian beef — though residents love those too.

It’s true: Chicagoans shame those who put ketchup on their hot dogs, especially if you go to the notorious institution Wiener’s Circle where patrons go to be openly ridiculed. Where to find the best Italian beef is up for debate, but Taylor Street’s Original Al’s Beef is widely recognized as a top choice. Know how to order your beef: wet (dipped in au jus) or dry, with hot and/or sweet peppers.

“As far as food goes, definitely stay away from downtown,” said Abbott. “Find local food.”

Beyond the dishes known to Chicago, the city is also home to several Michelin-starred restaurants, including the world-renowned three-star Alinea and Smyth. Two more restaurants have two stars, and 15 have one, with another 38 on the Bib Gourmand list, which denotes good quality food at a good value. More than 50 James Beard awards have been granted to Chicago restaurants and chefs.

In the West Loop, Randolph Street is known as “restaurant row” and offers many standouts from up-and-coming chefs to celebrity chefs.

“Chicago is one of the best food cities in the world and you can get world cuisine right here in our different neighborhoods,” said Lesniewicz. “There’s great taquerias, there’s amazing places for ramen and pho. … We have a great brewery scene with probably around 45 to 50 breweries in the city. You can get great southern food here in some of our neighborhoods on the southside like Bronzeville or Hyde Park.”

Deep dish is arguably the city’s most well-known local delicacy, but it’s rare that residents choose this style of pie over others. Most Chicagoans favor the tavern-style pizza with a cracker-thin crust and cut into squares.

“I think it’s a debate, but true Chicagoans don’t eat deep dish,” said Villegas. “A lot of us love that bar-style, pub-style pizza.”

The city’s public Chicago Transit Authority transportation system offers buses and trains through many neighborhoods. "L" trains — short for "elevated" — run above ground and circle downtown, giving the area its famed nickname, the Loop. Some trains lines run below ground too.

Metra commuter trains operate out of four major downtown stations and travel to and from the suburbs.

“We have an amazing network of public transportation that can pretty much get you anywhere you need to go in the city,” said Lesniewicz.

Thinking Chicago locals face harsh cold weather constantly is a false understanding, say residents. The city experiences all four seasons and anecdotally, most Chicagoans say winter isn’t as bad as it’s thought to be.

“We are so outdoors. One of the biggest misconceptions people have is they think it’s cold all the time, but it typically doesn’t even snow until maybe December but typically it starts in January. We have two to three months of snow and cold weather … but the rest of the year we’re outdoors,” said Abbott. “We’re outdoors in 40 and 50 degrees.”

When summer does roll around, Chicagoans can be found in the neighborhoods at each of their individual street and cultural festivals with vendors, food, and live music with several almost every week. Or at one of the city’s many beaches on the 30-mile span of coastal Lake Michigan with unobstructed views of the city skyline or riding bikes down the 18-mile coastal Lakefront Trail. Or at one of the city’s 600 parks.

“We have such a great array of parks,” said Lesniewicz. “As soon as its warm out, everyone’s outside in Chicago.”

After one snowy night, Abbott’s husband, a new resident from Toronto, parked on a street where lawn chairs were placed. He returned to find his car had been keyed. He did not respect the unofficial law of "dibs."

“Nobody understands that and thinks it’s weird when it does snow those couple times a year and there is a lawn chair, a kid’s swing set, a bird bath sitting in an empty parking spot,” said Abbott. “That is parking dibs. No, they don’t own the space, but they do because they took the time to unearth it. Do not park there or you will be greeted by a keyed car.”

While an ordinance says obstructing a public parking spot is technically not allowed, the city rarely takes action.

Architecture is one of the city’s strong suits, from notable buildings downtown like the corncob-shaped Marina City towers to the humble Chicago bungalows and two-flats.

“The Chicago bungalow is such a classic property loved by so many and you can find neighborhoods completely filled with a Chicago-style bungalow and others where you have them sporadically within a neighborhood,” said Villegas.

These homes were built primarily in the 1910s through the 1930s to serve its fast-growing population. The Chicago bungalow was designed to fit into the city’s standard lot and withstand its weather, according to the Chicago Architecture Center. These homes have brick construction with a low-pitched hipped roof with wide overhangs, a simple style, and lots of windows.

To get a quick lesson in the city’s downtown architecture, take an architecture boat tour.

“You learn so much about the city and one of our greatest attributes, the architecture along the river. It’s voted one of the best tours in the world,” said Lesniewicz.

Chicago is one of the rare metropolitan areas with two big-league baseball teams, the North Side-based Cubs and the South Side's White Sox.

It’s a spoken rule that residents must pick their team, there’s no waffling in baseball here.

“You can’t be both, that’s absolutely a stance,” said Abbott.