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Chicago is the ultimate city of neighborhoods, perhaps rivaling any other city in the United States. There are 77 neighborhoods officially recognized by the City of Chicago and that’s not including smaller nabes like Wrigleyville and Boystown which exist within a larger ‘hood. To understand Chicago is to give downtown its proper due, and then hop on the El train and zigzag your way around this patchwork of thrilling ethnic enclaves and historic districts.

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Andersonville, Chicago

Andersonville | Flickr photo courtesy of Zenia

A Swedish-American neighborhood for many years, only a few remnants of its Scandinavian past still remain. Lesbians did much to spiff up the area in the late ’80s and early ’90s and everyone else soon followed. These days it’s all about the energetic cafes, gastro pubs, furniture stores and cute shops lining Clark Street. Area highlights include the Swedish American Museum, the Neo-Futurists experimental theater, the pretty homes of nearby Lakewood-Balmoral and June’s big street fair, Midsommarfest.

Chicago awakens from its winter slumber every St. Patrick’s Day to fill the streets with shamrock green sweaters and drunken revelry. That’s thanks in part to Beverly, a South Side stronghold of Irish-Americans whose annual South Side Irish Parade is the largest neighborhood parade of any type in the country. Beyond that, it enjoys the distinction of having the highest elevation in the city, a slew of notable Irish-style pubs along Western Avenue, the Beverly Arts Center, and charming bungalows and historic homes.

Bronzeville, Chicago, South Side

Sunday Blues Jam in Bronzeville | Flickr photo courtesy of Greg Weber

This South Side neighborhood earns a fair comparison to Harlem in New York. The area’s not only historically significant for its cultural achievements among African Americans, but also as a place worth visiting today, thanks to art galleries (don’t miss the Stony Island Arts Bank), the occasional good restaurant like Harold’s Chicken Shack and Yassa, pristine Martin Luther King Boulevard and sunbathing at 31st Street Beach.

Aerial view of the Gold Coast

Gold Coast
Chicago gets a shot of New York’s Upper East Side in this tony lakefront hub filled with pricey high rises fronted by sharply dressed doormen. It’s a beautiful place just to walk around (and pop in to 360 Chicago, aka the Hancock Observatory), but beyond that there’s the so-called Viagra Triangle, a small park intersected by Rush and State Streets and Bellevue Place. It’s filled with chic shops and fancy restaurants with sidewalk seating, and is named for its nightlife catering to older gents and the gold-digging ladies who love them.

Hyde Park
Brainy Hyde Park is boastful of its accomplishments and it ought to be. It’s the location of the University of Chicago (which has produced the most Nobel laureates), the former residence of President Obama and close to the future home of his library. It’s more studious than it is fun, but strolling its pristine campus, touring the Robie House (a Frank Lloyd Wright masterpiece), brunch at Promontory and visiting the expansive Museum of Science and Industry (MSI) easily consumes a full day.

Chicago's Wrigley Field

Wrigleyville, a part of Lakeview

Looking for love in the big city? Head to Lakeview, a sprawling North Side neighborhood that is home to twenty- and thirtysomething singles on the prowl who cram its infinite supply of date night restaurants and clubby bars (go to Wrigleyville if you’re straight, Boystown if you’re not) in search of love or at least a hookup. Tired of the bar scene? Spend a day at Wrigley Field, home to the 2016 Word Series Champions the Chicago Cubs (if you can snag tickets, that is).

Lincoln Park, Chicago

Lincoln Park | Flickr photo by Steven Vance

Lincoln Park
It’s hard to believe Lincoln Park was a former hippie mecca, but it’s no surprise that its brownstones and tree-lined streets eventually fell into the hands of the affluent. DePaul keeps things lively with college bars along Lincoln Avenue, the stylish Hotel Lincoln gives the area a boost of cool, and the shops and eateries at Armitage and Halsted are completely charming. But its most enviable features will always be its lakefront location, the zoo and the park for which it’s named. It’s also where the infamous St. Valentine’s Day Massacre happened. Rat-tat-tat!

Lincoln Square
The sound of oom-pah no longer emanates from the beer halls that once lined the streets of this formerly German-American area (although a few do exist), but this Northwest Side nabe is hard not to love. Its residents skew toward the kale-eating, double stroller pushing, NPR-listening types, but we can hardly blame them for their self-satisfied lifestyle. Lincoln Square is nothing if not an adorable collection of lovely boutiques, European cafes and eateries.

Logan Square
If an artist were to draw a caricature of the so-called hipster it would look a lot like the tattooed, mustachioed and skinny-jean wearing baristas who call this northwest nook their home. Here you’ll find artisanal beer halls, small batch donut shops and eateries that take the farm-to-table movement seriously. The actual square for which it derives its name is super pretty and it doesn’t hurt that the city’s new 606 elevated park runs right through the ‘hood.

Loop, Chicago, downtown, skyscrapers

The Loop

The Loop
So named because this is where a majority of the city’s El trains converge and make a literal loop around the central business district, the Loop is a mecca for tourists and locals alike. Here you’ll find an abundance of Broadway shows, the Chicago Symphony Orchestra, Maggie Daley Park, the Chicago Theatre, Millennium Park (home to “the Bean”), Grant Park, Willis Tower, and an impressive little museum you may have heard of called the Art Institute of Chicago, which contains 500,000 works and objects.

Second City, Chicago, Old Town, comedy

The Second City | Photo courtesy of the Second City

Old Town
Don’t expect a history lesson when visiting this Near North Side neighborhood. Despite its name, Old Town is basically known for two things: the enjoyable Chicago History Museum and the legendary house of sketch and improv, The Second City. The latter is the world-famous comedy institution that gave rise to the likes of Bill Murray, Tina Fey, Stephen Colbert, current SNL cast members Aidy Bryant and Vanessa Bayer, and many others. Book tickets in advance.

Pilsen mural | Flickr photo by Brian Lauer

Many folks scratch their heads upon learning that Chicago has the highest percentage of Mexican-Americans outside of Los Angeles (perhaps they hadn’t noticed all the taquerias), but it’s true—and ebullient Pilsen could appropriately be called “Little Mexico City.” Check out the many excellent restaurants (serving all kinds of food) and funky shops lining 18th Street, enjoy the colorful murals and don’t miss the National Museum of Mexican Art.

Pullman, South Side, Chicago

Pullman Historic District | Flickr photo by Sheila Scarborough

A neighborhood steeped in Labor movement history, Pullman got a big boost in 2015 when President Obama declared it a National Monument. Its location on the far South Side of the city makes it harder to reach, but the rewards are a leafy community lined with historic (and still occupied) row houses built for railroad magnate George Pullman’s workers. Those workers eventually rose up against him; the rest is a history you can discover via guided tour.

Magnificent Mile, Chicago, River North, Streeterville

Magnificent Mile | Flickr photo by Johan Fantenberg

Streeterville and River North
The tourist name for Streeterville is the Magnificent Mile, a reference to the cluster of flagship stores and high-end retail clustered around North Michigan Avenue (it’s also home to Navy Pier). But the locals who live here love it for its sleek high rises, plethora of restaurants and brunch spots, and proximity to the Loop. Walk west of the Mag Mile and you’re smack in the middle of River North, home to numerous nightclubs, art galleries and an undeniably dynamic restaurant scene.

West Loop
Nevermind that loft living reaches its apex in this formerly industrial corridor, the West Loop and nearby Fulton Market area are hot, hot, hot right now, thanks to a mad crazy influx of restaurants that seem to open and close almost daily. Among them are a trio of eateries from Top Chef superstar Stephanie Izard (Girl and the Goat, Little Goat and Duck Duck Goat), two entries from Rick Bayless (Leña Brava and Cruz Blanca) and literally dozens of others.

Wicker Park, Chicago, Midwest

Wicker Park | Flickr photo by ercwttmn

Wicker Park and Bucktown
New Yorkers won’t admit it, but before Williamsburg reinvigorated the term “hipster,” the young and artsy (including the likes of Liz Phair and the Smashing Pumpkins) began migrating en masse to a cozy corner of Chicago’s near Northwest side and lining it with thrift stores, record shops and cheap cafes. Those days are long gone and Wicker Park and sibling neighborhood Bucktown are now affluent anchors of urban cool, boasting top-notch clubs, bars, eateries and shops.




Tagged: Chicago

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Jason Heidemann

Jason Heidemann

Jason is a Lead Content Specialist for Expedia Group, and manages content initiatives across numerous Expedia-owned brands. His work has been featured in the Chicago Tribune, Time Out, the Huffington Post, Chicago Magazine, Passport and many others.

3 thoughts on “These 18 neighborhoods are why Chicago is America’s dream city”

  1. Lakeview is much more than Wrigleyville and Boystown bars! We have a lot of lakefront greenspace and many nice restaurants and shops.

  2. Fantastic post, I recently moved to Chicago in a D.R. Horton home and I love it, and the more I learn about surrounding areas the more I love it. Chicago is nothing like I assumed it would be, so much more beautiful and filled with some incredible people. You really cannot go wrong here.

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