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The south side neighborhood of Douglas stretches along Lake Shore Drive from 26th Street south to Pershing Road. As one of Chicago's earliest settlements, Douglas' long established community offers more than just a history lesson. But it would be a shame to jump into present-day life in Douglas without a little background info on its founder: lawyer and politician Stephan A. Douglas. First development of the are began in the mid 1800s when Mr. Douglas purchased a big chunk of land along Lake Michigan, roughly three miles south of Chicago's emerging downtown metropolis. After building himself a home on 35th Street (Douglas' southern border), the philanthropic pioneer donated a good portion of his property to worthy institutions like churches and schools. It wasn't long before families and working professionals were drawn to the neighborhood and Douglas became a viable Chicago community with scenic waterfront landscapes.

Hard to believe an area no bigger than two square miles could pack in four good-sized public parks and a beach, but even with its development, the neighborhood managed to maintain a generous portion of lush green space and a popular sandy spot for lounging by the lake. You can thank good 'ole Stephen Douglas for that (literally) as his tombstone sits in the community's serene Woodland Park. Just two blocks north of Woodland is Groveland Park, which is a favorite among residents for picnics and quiet walks. The most popular outdoor spot in Douglas, though, is Lake Meadows Park. This is where you'll find moms and dads relaxing while their little ones romp around in the park's playground. And Chicago's sprawling Burnham Park stretches down into Douglas, too, offering locals access to the 20-mile-long Lakefront Trail, plus plenty of grassy expanses and a large beach protected by jetties on either side.

While you're in Douglas, you may as well make the most of its waterfront location. Swing by La Fuente, where you can indulge in steak tacos and veggie burritos as you take in views of Lake Michigan. Dinner without panoramic sightlines may not be as picturesque, but Mississippi Rick's proves it can be twice as delicious. From tender turkey legs to spicy jerk chicken, this place serves up the best soul food in the neighborhood.

You've probably already guessed, given its history, that the homes in Douglas pack in some serious charm. From vintage brick buildings and graystones to newer townhomes and high-rise condominiums, the housing options here have a lot to offer. A one-bedroom condo in an older brick flat or a mid-rise unit will typically range from $100,000 to $200,000. More spacious townhomes and three-bedroom residences start in the $400,000s, but can easily reach the high $600,000s.