In Rogers Park, consider this bright two-bedroom condo located a few blocks from the lake and the Howard CTA station. Listed for $254,900, the second-floor unit has an updated kitchen, in-unit laundry, and a rear porch. The sunny living room features a charming decorative fireplace, crown molding, and built-in shelving.

For $145,000, get a one-bedroom in an attractive 1927 courtyard building in Old Irving Park. At 900 square feet in size, the unit is roomy for a one-bedroom and features a formal dining room, an updated bathroom, and a walk-in closet—a rarity among buildings this age. The North Side property is convenient to the Kennedy Expressway as well as the CTA Blue Line.

Lincoln Park is known for its multimillion-dollar mansions, but there are some decent options for buyers working within a more modest budget—especially in some of the older high-rises along the park. Listed for $374,900, this updated two-bedroom unit on the ninth floor of a mid-century building offers an open living and dining room, a newer kitchen, and glimpses of Lake Michigan. The views get even better from the building’s rooftop pool deck.

With an asking price of $148,000, this historic three-bedroom single-family home in Austin is one of the more affordable options on the list. That said, the 1891 property—designed with a mix of Victorian and Italianate architectural features—could use some updating. Still, the West Side fixer-upper has good bones and plenty of original touches like hardwood floors, carved wood fireplace, window casings, and pocket doors. It’s also close to the CTA Green line and Austin branch library.

For some first-time buyers, location may be more important than space. If that’s the case, consider this eye-catching architect-owned one-bedroom in downtown Chicago’s iconic Marina City complex. Perched on the 41st floor of the eastern tower, the unit has been thoughtfully restored in a way that celebrates the building’s midcentury modern roots. The property is seeking $290,000 and includes a private northwest-facing balcony.

In Chicago’s popular West Loop neighborhood, it’s become increasingly difficult to find a decent two-bedroom for less than $350,000. This bright loft along Van Buren Street, however, can be had for $307,500. The home boasts recently refinished hardwood floors and a newly renovated kitchen and bathroom. Building amenities include a fitness center and roof deck.

Live steps from Promontory Point and the University of Chicago in this East Hyde Park condo, available for $250,000. Located on the third floor of charming vintage building, the three-bedroom, two-bathroom property includes old school touches including a wood-burning fireplace, wood moldings, and recently refinished original hardwood floors.

In Chicago’s West Lawn neighborhood, $259,900 buys this large single-family home dating back to 1903. Little about the four-bedroom property’s interior seems outdated thanks to updates to its kitchen and bathrooms and recently replaced windows. The West Side residence stands on a double lot, creating a large back and side yard. The backyard chicken coup isn’t included in the asking price but is “negotiable,” according to the listing.

Renovated in 2018, this classic brick single-family residence dates back to 1915 and sits on an oversized 181-foot-long lot in Chicago’s Washington Park neighborhood. The three-bedroom home has a large picture window in the living room, a newer kitchen, a dedicating dining room, and a finished lower level. The South Side property offers convenient access to Washington Park proper as well as stops for both the CTA’s Red and Green lines. It’s asking $232,500.