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5 homes for sale in Chicago, home to this year's basketball Cinderella story

This three-bedroom, one-bath condo in Hyde Park is on the market for $369,000.

Ultimate Realty Group

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For years now, Chicago has served as one of Donald Trump's many punching bags, fixated as the now-president is on the city's rate of gun violence. This month, though, the Windy City is back in the news for heartwarming reasons, thanks to Loyola University Chicago's surprise success in this year's NCAA men's basketball tournament. And though there's a lot of rightful excitement about the Rambler's Final Four matchup against the University of Michigan on Saturday, Chicago is a lot more than just its sport teams (or its crime rate). The city is home to Second City, the leading club and theater/improv school, world-class scientific and cultural institutions such as the Field Museum and the Art Institute of Chicago, a wide-ranging culinary scene, several prestigious universities, and Oprah, to name just a handful of highlights.

Also, Chicago has something approaching respectable public transportation, a rarity in American cities. Lake Michigan is resplendent in both good and bad weather (though the beaches are far more pleasant when it's warm out). It's only a short drive to the Mars Cheese Castle in Kenosha, Wisconsin, which was recently redesigned to actually look like a castle, though regretfully it is not constructed out of actual cheese. And, most notably in my view, Chicago served as the setting for ER, the greatest medical drama ever to grace network television. 

Chicago is also quite a bit more affordable than New York, despite being the third most populous city in the United States, with a median home sale price of $292,100 paling in comparison to Manhattan's steep median sale price of $1,189,011.

If you're contemplating a big move without giving up on big-city life, here's an idea of what you can buy out there for less than the cost of a shoebox in New York.

Ultimate Realty Group

5744 South Kenwood Ave., #4, Hyde Park

This elegant three-bedroom, one-bath condo (also pictured at top) in a Victorian townhouse is located in Hyde Park, a neighborhood on Chicago's South Side that's home to the University of Chicago, some beautiful landmarks, and, if you count Kenwood as part of the neighborhood, occasionally Barack Obama. The condo has high ceilings, hardwood floors, a gorgeous dining room with a built-in hutch, and a backyard and deck. The owners are looking for $369,000.

Parkview Properties & Investments, Inc

2040 North Cleveland Ave., Apt C, East Lincoln Park

Lincoln Park is a ritzier neighborhood on Chicago's North Side, home to beloved restaurants (Alinea, Pequod's Pizza, de Quay) and the popular Armitage Avenue shopping district, and offering easy access to the Lincoln Park Zoo and Conservatory. This three bedroom, two-bath townhouse is located in the middle of the action, and boasts a well-lit two-level living room, a chef's kitchen with a Sub-Zero fridge, a separate laundry room, and a private brick patio. The asking price is $655,000. 


2039 West Crystal St., #1, Wicker Park

Wicker Park is a neighborhood with lots of quirky shops, bars, cafes, and an art community that's now dwindling thanks to real estate price pressures. Still, there's a lot to do in Wicker Park and neighboring Bucktown. This sunlit split-level, located just one block from the strip on West Division Street, features two bedrooms and two baths on it's top floor and another bedroom and bathroom downstairs, plus it includes a massive family room, a fireplace, stainless-steel appliances, central air, and a rear deck. It's listed for $545,000.


2041 North Sawyer Ave., Logan Square

Logan Square has usurped some of Wicker Park's cool in recent years, thanks to its ample bar, club, music, and art scenes. For folks with money to burn, or an urge to take on tenants, this spectacular Greystone building is a two-family, with a two bedroom apartment downstairs and an upstairs three-bedroom unit for tenants. The house has sunrooms, chef's kitchens, a shared yard, and a front porch swing. The listing price is $850,000.


3755 North Wilton Ave., Apt 3SE, Wrigleyville

This two-bedroom, two-bath condo is just a few blocks from the famed Wrigley Field (hence the neighborhood's name). The condo has a massive master suite with a skylight and picture windows, a living room and kitchen covered by a custom tray ceiling, elegant molding, an electric fireplace, and a private balcony. The owner is looking for $450,000.