By Kerrie Kennedy

Contributing writer

In most American cities, "Uptown" is where the rich folks live. Traditionally located far from the hustle and bustle of downtown, "Uptown" conjures up an image of wealth and privilege.

Chicago's Uptown, bounded by Irving Park Road, Foster Avenue, Lake Michigan and Clark Street, was once no exception. Its rich history dates back to before the turn of the century, when the suburban-like area was developed for upper-income residents seeking housing along the lakefront. Many of them built large homes on large city lots in Uptown.

Once home to such glamorous residents as Bob Hope, Gloria Swanson, Douglas Fairbanks, Mary Pickford and Charlie Chaplin, Uptown's star began to fade by the 1930s, when the neighborhood experienced an exodus of its wealthy residents.

The glamorous image of Uptown was eventually shattered during the post-World War II housing shortage. Large single-family homes were razed to make way for large apartment buildings, and many of Uptown's large, gracious apartment buildings were divided into smaller, more-affordable units.

"Uptown" had become decidedly "downtown." Inexpensive rents attracted low-income tenants, and from the 1950s through the 1970s, Uptown struggled through hard times.

Eventually, Uptown's image became so unsavory that real estate agents avoided uttering its name at all. Instead, they created "sub-names" such as Margate Park, the area north of Lawrence to Foster; Buena Park, the area from Irving Park to Montrose; and Sheridan Park, the 21-block historic district bounded by Broadway, Clark, Lawrence and Montrose.

But never write off a has-been star: there's always the possibility of a comeback. In the case of Uptown, it's been a slow but steady rise, but a comeback nonetheless. Over the past 15 years, Uptown has been in the process of a major makeover. Real estate experts estimate the volume of condo conversions in Uptown is on a par with that of the West Loop.

Of course, Uptown's rise hasn't been without a hitch. Home to many low-income Chicagoans, many of them immigrants, Uptown has lost hundreds of government-subsidized rental units as well as hundreds of non-subsidized affordable units to condominium conversions.

Ironically, perhaps, those condo conversions have been providing more "affordable" housing to scores of homeowners who have been priced out in other lakefront neighborhoods such as Lincoln Park and Lakeview. Slowly but surely, these new homeowners—and their buying power—have changed the face of Uptown.

A large chunk of the condo conversions have taken place along the lake in Uptown, the area east of Broadway from Irving Park on the south to Foster on the north. The Clark Street Corridor—running north from Montrose to Foster Avenues on the western edge of Uptown—is undergoing a rebirth with new condominiums, retail and restaurants. And in the historic landmark area of Sheridan Park, buildings that once attracted well-to-do residents are once again doing the same, with many conversions that feature elaborate original moldings and architectural details.

With residential development surging on all sides of the neighborhood, experts say the future of Uptown really depends on the development of its commercial district.

"The goal is to develop retail and commercial in Uptown and bring money and jobs here," says 46th Ward Ald. Helen Shiller. "There are huge possibilities for Uptown."

Until somewhat recently, Uptown's commercial sector consisted mainly of small, ethnic, owner-operated businesses. While it was possible to get incredible barbequed Chinese duck in Uptown, for years residents had to go elsewhere to get their clothes dry cleaned. Perhaps it was inevitable that Uptown's commercial sector had to grow along with its new residents.

A Border's Bookstore, part of a once controversial 37-unit condo development on Broadway and Racine, was the first whiff of change for Uptown's commercial sector. Now open for some time, Border's is one of several national retailers (T-Mobile to Target) who have set their sights on the neighborhood. New small businesses that cater to Uptown's new yuppie residents (sushi restaurants to coffee bars) have sprouted up as well.

After years of delays, work is underway at Wilson Yard, a $140-million dollar development located along Broadway from Montrose north to Sunnyside. When complete, Wilson Yard—formerly a CTA yard—is to feature a 180,000 square-foot Target store; 25,000 square feet of smaller retail; a 99-unit apartment building for seniors; a 78-unit rental housing building; and nearly 700 total parking spaces. A new Aldi grocery store at the north end of the site is already open.

According to Joyce Dugan, president and CEO of Uptown United, a development corporation that works closely with the Uptown Chamber of Commerce, Uptown's future may lie in its past. Once the center of a bustling entertainment district, Uptown's secret weapon may well be its historic venues, including The Green Mill, the Riviera Theater, the Aragon Ballroom and the Uptown Theater.

"There's already been a lot of development in these pockets [near Broadway and Lawrence]," says Dugan, a 40-year Uptown resident. "I think Uptown's entertainment district, especially if the Uptown Theatre is purchased, will eventually become a huge magnet. There's already been talk of more mid-size venues nearby. I think we'll see development continue around these venues."

While Uptown isn't the haven of cheap housing it once was, new construction and condo conversions in this neighborhood are still well-priced compared to other lakefront neighborhoods. But even that may not last long. With Uptown's star on the rise, it may just be a matter of time before Uptown is once again the place where the rich folks live.

For Sale In Uptown

—Beacon Hill Condominiums. Situated high atop an extra-large landscaped lot at 4708-10 N. Beacon in Sheridan Park, this new construction development features eight extra-spacious two- and three-bedroom residences with such details as wide-plank walnut-stained hardwood floors; wood-burning fireplaces with custom mantels; front terraces; a high-end trim package; one parking space per unit; and an upgraded common entry area. The two penthouse units feature private stairs to private roof decks. Not yet listed on the MLS, buyers still have time to pick out many of their own finishes. Prices range from $350,000-$500,000.

—Rainbo Village. Set on the historic two-plus-acre site of the former Rainbo Roller Rink at 4836 N. Clark Street, Rainbo Village features 127 soft loft condominiums, duplexes and townhomes as well as 15,000 square feet of retail space. The lofts, priced from $262,900-$451,900, feature 10-foot ceilings, private balconies and floor-to-ceiling windows. First deliveries are planned for this summer.

—The Sheridan Grande. Sales have passed the halfway mark at this 70-unit, luxury condominium at 4848 N. Sheridan Road. Prices range from $284,000-$384,000. One deeded parking spot is included with the purchase of a three-bedroom unit. Immediate delivery is available.

—Winthrop Terrace Condominiums. Nineteen renovated condominiums are available at 4936-4938 N. Winthrop in Margate Park. Prices range from $195,900-$299,900.

—Chase Park Commons. Fall occupancy is scheduled for buyers at Chase Park Commons, a 42-unit mixed-use new construction development located at 4717-4747 N. Clark. Prices range from $389,900-$416,900 for a three-bedroom, three-bath, 1,500 square foot residence with one garage space included.

—4420 N. Clark. More than half of this new construction project's 32 units have been sold. Remaining two-bedroom, two-bath units are priced at $322,500.