From River North to the Gold Coast, to Wicker Park and the South Loop, discover some of Chicago’s best neighborhoods.
Boundaries: Bucktown: Between Fullerton Avenue south to North Avenue, from Western Avenue east to Kennedy Expressway/Ashland Avenue; Wicker Park: Between North Avenue south to Division Street, from Western Avenue east to Ashland AvenueGoats used to graze in what is now considered one of the hippest and trendiest neighborhoods in Chicago — if not the country. The popular theory is that Bucktown got its name from the male goats, or bucks, that were raised by the Polish immigrants who fled their war torn country in the 1800s. Throughout the years, Bucktown saw many waves of immigration, primarily Polish until World War I, then Jewish in the early 1900s and Latino around 1960.It was in the 1980s that Bucktown began to evolve into the artistic community that it is known as today. The lower rents in the undiscovered area and its proximity to downtown made it a natural choice for musicians and artists looking to stretch their bucks a little further. As the area became more popular, rents began to climb, pushing people south to Wicker Park. The dividing line between the two is North Avenue, with Bucktown to the north and Wicker Park to the south.“Because of its infrastructure, [Bucktown’s] one of the easiest neighborhoods to get in and out of,” says Thaddeus Wong, co-founder of @properties, a Chicago real estate brokerage firm. “It’s a very diverse economic neighborhood. You’ve got $2 million homes scattered throughout the neighborhood with condos, lofts and townhomes.”Serious rehabbers seek out Wicker Park for the unusual, for instance, this converted firehouse and a “pod” house located here was the grand prize architectural winner for a “small spaces” exhibit. And you can trade up your old threads for cash at the Crossroads Trading Company.
Boundaries: Between North Avenue south to Chicago Avenue, from LaSalle Avenue east to Lake MichiganOld money and stunning lake views characterize this hot neighborhood that runs contrary to the Chicago phrase: “cooler by the lake.” Oprah once lived on the border of this high-priced community, where homebuyers can pay millions for a two-bedroom condo. And if you’re into “intentional living,” or sharing humongous spaces commune style, this area has some of Chicago’s largest old homes that could fit the bill. “People are drawn to this area because of the nightspots, the good food, its proximity to the lake and to the business district,” says Prudential Preferred Properties Realtor Carla Walker.The main commercial center for this neighborhood is Oak Street, the Rodeo Drive of the Midwest. Hermes, Versace and Gucci clothing stores mingle with four-and five-star restaurants offering outdoor seating in the summer. Oak Street runs right through the heart of an area known as the “Viagra Triangle.” This slice of the city, bounded by Rush Street, State Street and Chicago Avenue is nicknamed for the affluent, white-haired men that can be seen courting well-dressed women in their 20s at area singles bars. Coincidentally, Hugh Hefner’s original playboy mansion, at 1340 N. State St., is just down the street from the Viagra Triangle.During summer, Rush Street Concerts at the landmark St. James Cathedral showcase live performances for an hour.
Boundaries: Between 51st Street/Hyde Park Boulevard on the north, 59th and 60th streets on the south, Washington Park on the west and Lake Michigan on the eastWithout question, one of the most famous residents is the 44th President Barack Obama. Seven miles from the Loop on the South Side of Chicago, you’ll find several of the country’s more prestigious institutions. The University of Chicago, renown for producing over 87 Nobel Prize laureates, including two 2013 award recipients for economics, is here. Chicago Blues legend Muddy Waters played the standing-room-only gig with the Rolling Stones at the Checkerboard Lounge in 1981.
Boundaries: Between Diversey Parkway south to North Avenue, from Clybourn Avenue east to Lake MichiganIn the 1800s, the area that is now one of the most fashionable places to live in Chicago was mostly swampland and forest. Now, it’s a magnet for singles in their 20s and 30s, many of whom stay to start families here. The neighborhood is home to two private schools with great reputations for the education they offer kids from junior kindergarten through 12th grade. The community is very much like a college town within the big city, with a large variety of shopping, restaurants and nightspots all in close proximity.People who live here don’t really need a car to get around, which is a good thing, because parking here is scarce. Residential streets are lined with cars bumper to bumper, and most of the streets require a permit to park. The neighborhood’s young energy is fed by the 3,000 students who attend DePaul University’s oldest and largest campus in the heart of Lincoln Park. Named for Chicago’s largest park (with more than 1,200 acres), the neighborhood offers an abundance of outdoor activities, including bike trails, jogging paths and athletic fields. There really is not a main artery in Lincoln Park, because every major street running through the neighborhood is a hub of commercial activity.A brand new upscale retail and luxury living development, New City, is underway in the busiest shopping corridor in Chicago. And for the bargain-hunter, Lincoln Park is headquarters to a truly unique enterprise: Millionaire Rejects is the ultimate resale shop. Want a great place for a first date? North Pond restaurant made the list of six best romantic spots in Chicago.
Boundaries: Between Michigan Avenue to the east, Chicago Avenue to the north and the Chicago River to the south and west.This area of Chicago was uncharitably called a slum until real estate developer Albert Friedman began leasing out buildings to art galleries, photographers and agencies, all looking for economical office and display space. The transformation has been exceptional.Today, River North has the greatest concentration of art galleries in the country — over 100 clustered in the gallery district on Superior and Huron — trailing only New York. The world’s largest commercial building, the Merchandise Mart, at 4.2 million square feet, is here. (Google Inc. is a tenant.) And Donald Trump built Trump Tower on Wabash, the tallest residential skyscraper in the western hemisphere and popular home for athletes and celebrities (Chicago Bulls point guard Derrick Rose bought a condo).
Boundaries: Between Addison Street south to Belmont Avenue, from Western Avenue east to Lincoln AvenueGerman and Swedish workers settled in what is now Roscoe Village in the late 19th century when it was between two industrial areas on its eastern and western borders. Tough economic conditions during the Great Depression closed many factories and businesses in the area, and development slowed. The real estate market began to pick up in the 1980s, however, when developers began to see the advantages of its location only four miles away from the Loop.
Like a village within the city, this quaint community is very popular with young families. Parents are often seen pushing strollers past the shops with colorful awnings, small restaurants and trees that line Roscoe Street, the neighborhood’s main thoroughfare. Vintage brick walkups and well-maintained frame houses with front porches help maintain the atmosphere of this family-oriented community. Along with the newer designer boutiques that have sprung up in the area, residents of Roscoe Village can enjoy the largest concentration of antiques stores in the Midwest, located along the neighborhood’s Southern border.
Boundaries: Between Jackson Boulevard south to 16th Street, from the Chicago River east to Lake Shore DriveIn the early 1900s, the area that is home to some of Chicago’s top tourist attractions and the country’s largest media and arts college was filled with brothels, saloons and pawnbrokers. Known as the Levee District, the neighborhood housed one of the world’s most famous bordellos at the time. Prostitution flourished in an area protected from law enforcement by organized crime and crooked politicians.Today, luxury high-rises and modern townhomes are being built in an area once known as “Satan’s Mile,” a stretch from Van Buren to 22nd that was so crime-infested an 1896 judge ruled that a man deserved whatever he got for entering it. Generally considered a slum, the South Loop was a far cry from the expensive neighborhood it is today. Now a thriving community where visitors flock to tourist spots like the Shedd Aquarium, Adler Planetarium and the Field Museum, the South Loop is an area that draws executives who enjoy its proximity to Lake Michigan and the downtown business district.“For many of my clients who choose to buy in the South Loop, this is not their first home,” says Walker of Prudential. “It’s the next step up for young people. A lot of people who have homes in Indiana or the suburbs, and they want space downtown, that’s where they’re buying.”That South Loop has become a premium destination is reinforced by the continuing developer buzz and re-imagining of high-rise living.
Boundaries: Between Grand Avenue south to the Chicago River, from Michigan Avenue east to Lake Shore DriveDevelopment and home sales in Streeterville, southeast of the Gold Coast, remains strong. “Anytime you’re within a few blocks of Michigan Avenue, home values will be higher,” says Gail Lissner, a vice president of Appraisal Research Counselors. “More established, more well-located areas will do better even in a soft housing market.”The most spectacular apartment space in the country debuted here, located at 500 N. Lakeshore Drive. The people who live in Streeterville are moving up, literally, with taller highrises being built every year. Nicknamed the “platinum coast” by some Realtors, apartment buildings and condos in this area come with more than the usual amenities. Some come attached to banks, athletic clubs, convenience stores, hotels and in one case — the Residences at River East Center — a 21-screen movie theater and bowling alley.Parking in this neighborhood, which has Northern Michigan Avenue as its western border, is expensive. Expect to shell out about $250 a month to rent a parking space. Residents can save the $3,000-a-year parking expense by taking advantage of the taxis that come right to their door.
Boundaries: Between Lake Street south to Eisenhower Expressway, from Kennedy Expressway east to the Chicago River
Oprah built her Harpo Studios empire here, before this former warehouse district became an up-and-coming neighborhood of contemporary lofts, midrises and art galleries. “Most buildings are between five to seven stories,” says Jeneane Ally, a Realtor with Rubloff Residential Properties and a West Loop resident. “Developers are taking the existing buildings, gutting them and making them look like new.” The West Loop Community Organization has fought to control density and limit the number of high-rises that can be built here.With larger units, two parks in the area and more parking available than other neighborhoods near the Loop, the West Loop is a draw for young families. Within its borders is the prestigious Whitney M. Young Magnet High School, alma mater of first lady Michelle Obama. Enrollment for this public school, which consistently ranks as one of the top high schools in Illinois, is highly selective and determined through test scores and academic standing.Not to be missed is the SoHo of the Midwest, the monthly Randolph Street Market, a one-of-its-kind outdoor and indoor arena for the collector, antique shopper and flea market connoisseur.
Boundaries: Between Division Street south to Grand Avenue, from Western Avenue east to Damen AvenueChic boutiques and trendy nightspots continue to pop up in this west town village south of Wicker Park. Decorated with beautiful, ornate churches, the neighborhood has preserved the cultural heritage brought to it by German, Polish and Ukrainian immigrants in the late 19th and early 20th centuries. Although most of its residents are not of Ukrainian descent, the Ukrainian food here is some of the best in the city, and visitors can still hear the language spoken on backyard stoops and in neighborhood businesses.Division Street and Damen Avenue are the community’s commercial centers with a variety of shops and restaurants that are transforming this quiet village into a hot neighborhood for homebuyers. “In the last two years, we’ve seen a lot of younger professionals moving here,” says Helen Sobel, a broker associate for Baird & Warner. “It’s usually a young couple starting out with their dog. They can get a three-bedroom condo for $350,000 in the area that they can grow into.”The Ukrainian Village is a very eclectic neighborhood containing low-rises, single-family homes and older Victorian homes that are inhabited by families who have lived here for decades. “It’s got a very Chicago feel to it,” Sobel says. “There are a lot of front porches still in the area, and people saying ‘hi,’ when you walk by.””King of Concept,” Restaurateur Jerry Kleiner and Chicago, who brought style to dining on Randolph Street, converted a brick garage into a show home in the West Town section of Ukrainian Village.