Last week, I wrote about affordability in Chicago, specifically examining what is available on the North Side at appropriate prices for their locations. The fact that almost all the properties went contingent after the article was published shows that inventory is indeed low, as it typically is this time of year, and those asking prices were quite reasonable. So I thought I’d flip it and go pay a visit to the other side of the city. Where does the South Side officially begin? There are various opinions: some argue it starts at Roosevelt Road, while others believe the boundary kicks off at Cermak Road. For this round-up, we’ll use the former definition (I cannot imagine excluding a property from the Prairie Avenue neighborhood, conveniently close to Loop and lakefront). Also, let’s not forget the South Side represents about 60% of Chicago’s total land area. With a variety of housing options, the South Side is definitely worth exploring.

1727 S Indiana Ave #223, Chicago, $229,900

Photo courtesy of Redfin

This one-bedroom, one-bathroom condo is located right around the corner from the historic Glessner House in the South Loop’s Prairie Avenue. Originally constructed in 1905 as the Eastman-Kodak plant, the building was designed by architects Hill & Woltersdorf and was converted into the Prairie District Lofts in 1992. A hint of its history can be found in the limestone above the southern entrance of the five-story building, which features sculpted camera. At just over 700 square feet of living space, this typical loft boasts exposed brick walls, wooden beams, a gas fireplace, and an in-unit washer/dryer. The $452 monthly HOA fees cover a rooftop deck, fitness center, and on-site management.

2545 S Dearborn St #510, Chicago, $320,000

Photo courtesy of Redfin and VHT Studios

Not too far from our previous listing stands an old warehouse where thousands of sets were constructed and stored for the Chicago Civic Opera. In 2008, the building was converted into 93 residential units and renamed the Opera Lofts. This particular unit spans 1,141 square feet and features two bedrooms, two full bathrooms, and an east-facing balcony. The pet-friendly property includes one indoor parking space and monthly HOA fees of $369. I thought it was interesting that the current asking price is actually lower than when the condo last sold almost six years ago at $324,650.

4102 S Cottage Grove Ave Unit 3S, Chicago, $349,900

Photo courtesy of Redfin

In the Bronzeville/Grand Boulevard area, we have a property that just makes the cut with a listed price of $349,900. The words “Columbian Block” are intricately carved into the historic exterior, which dates back to the 1870s. This 2,500-square-foot top-floor condo duplex features an open-concept layout that comes with three bedrooms, three full bathrooms, and a large kitchen. There are two outdoor spaces: a balcony off the kitchen and another one adjacent to the primary bedroom. With a designated exterior parking space, the property’s monthly assessment is quite reasonable at $309.

5209 S Ingleside Ave #2, Chicago, $287,500

Photo courtesy of Redfin and VHT Studios

This refreshed three-bedroom, two-bathroom condo is situated in the Stratford Building in Hyde Park. The front sun room allows additional natural light to flow into the interior, which spans just over 1,500 square feet. The rear galley kitchen, adjacent to the dining room, seems functional and well-designed. It’s worth noting that the property, which includes $550 HOA monthly fees, features central air conditioning, an amenity that is not always a guarantee in historic apartment buildings. The property is in an excellent location, as it is within walking distance of Washington Park, University of Chicago, and all that the neighborhood has to offer. 

5108 S Woodlawn Ave #3G, Chicago, $259,555

Photo courtesy of Redfin

Let’s stay in the middle of the Hyde Park/Kenwood area with this top-floor two-bedroom, one-bathroom condo that has just gone contingent as of this writing. Spanning over 1,300 square feet, the interior feels bright and airy, which is definitely helped by its white walls, sun room, and eastern-facing windows. Speaking of which, I particularly love those casement windows. The butler’s pantry has been converted into a laundry room, complete with a hook-up for an in-unit washer and dryer. The $414 HOA monthly fees cover heat, water, gas, and snow removal.