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The land where Ashburn is today was annexed to Chicago in 1889 as part of a subdivision of the town of Lake. Known as Clarkdale back then, this rural southwest section was slow to develop for many years. Swedish, Dutch and Irish settlers were the first to move into the region, but still population growth during the first three decades of the twentieth century was at a crawl. The baby boom following World War II changed all that, however, and the area saw tremendous expansion in the later half of the century. Today, the quiet and shady community of Ashburn centers around family life, with modest homes, good schools, and a wealth of recreational activities that create almost a suburban feel. Ashburn housing stock consists of vintage brick houses, split-levels and Cape Cod-style dwellings, most with garages as well as front and back yards. The majority of real estate in Ashburn is single-family homes, with less than ten percent of residences in the neighborhood being rentals. The average home sales price in this Chicago neighborhood is in the low $200,000s, however there are places on the market in the $300,000 range, too.

Ashburn is more of a residential haven than commercial hotspot, so it may not have a lot to offer avid shoppers. But don't tell that to the folks at Gina's Fashions. Gina's offers a variety of women's wear from business to casual and Soul II Sole Shoes has a great selection of footwear for the whole family. However, for a wider collection of retailers, Ashburn is close to both the Ford City Mall and Scottsdale Shopping Center, which means residents can still indulge in weekend shopping sprees without heading too far from home.

For getting in, out and around Ashburn the CTA has several bus lines intersecting the neighborhood. The South Kedzie and the South Pulaski bus lines run north and south, while the 79th Street and 87th Street bus routes run east and west. For Metra travel the South West Service commuter line has an Ashburn stop at 83rd Street and Central Park Avenue. You can use this line to travel to Chicago's Union Station downtown or out to the end of the line in suburban Manhattan, Illinois.

One thing you don't have to leave Ashburn for is good food. The neighborhood is dotted with delightful restaurants that cover a span of tastes and budgets. Paisano's is a great place in Ashburn for Mexican cuisine, but for Italian, you have your pick of pizza options. If you like your pies thin, crispy and delicious, then check out Nick & Vito Pizzeria. Prefer pizza of the deep dish variety? Villa Rosa Pizzeria might be your bag. Another favorite among the locals is Waldo Cooney's Pizza (which also has great chicken and seafood). Cooney's has several locations on the south side including this one in Ashburn. A good way to start off the day with a hearty breakfast is by heading over to Karina's Family Restaurant, which also serves up a mean patty melt for lunch. Spice it up then cool it down at Gertie's Ice Cream & Lindy's Chili. In business since 1901, this neighborhood mainstay is actually two restaurants in one with a hot side for chili and cool side for ice cream, naturally.

Unfortunately for some, but fortunately for others, there are not a lot of bar hopping options in Ashburn. This can be seen as an asset for family-oriented folk but a bummer for residents who crave the nightlife. That doesn't mean local revelers are totally out of luck. There are a few neighborhood haunts like Locascio's Sports Bar, the Old Lamp Lighter, Groucho's Bar and Grill and Bluebird to quench patrons' thirst. Locascio's is a comfortable spot where you can get a few beers, munch on bar snacks and keep track of the home team's score on TV. Just down the street is the Old Lamp Lighter, offering an alternative to the sports theme. Regulars here prefer to play tunes on the jukebox and shoot pool than watch the game. To hear local Chicago and suburban rock acts, Groucho's is a favorite south side hangout, but if bowling is your leisure activity of choice, the Bluebird has 28 lanes - which can be enjoyed along with a slice of pizza and a beer.