Up to $250,000
Historic row houses on a national monument site, a small-town feel in the burbs, a hip enclave just outside the city
In the City
During much of the 20th century, this Near South Side neighborhood, which straddles the Douglas and Grand Boulevard community areas, was the epicenter of African American civic and cultural life in Chicago, a heritage honored by the creation in the 1990s of the Black Metropolis–Bronzeville historic district. The district encompasses nine landmark buildings and many graceful prewar row houses and apartment buildings. The neighborhood is also home to the Illinois Institute of Technology, which boasts a striking collection of modernist buildings and lends a youthful dynamism to the area. Bronzeville has witnessed an influx of investment from developers and public agencies, delivering new housing, retail establishments, and infrastructure improvements. Yet homeownership here is still very much in reach for cost-conscious buyers. “Our budget was $200,000 for a two-bedroom condo,” says resident Nathan Anderson, “and we had a lot of options.”
Like a number of residents, Ellen Kaulig and her partner got their tantalizing first glimpse of this picturesque Far South Side neighborhood while on the annual Historic Pullman House Tour. The quiet blocks of narrow red-brick row houses—designed by architect Solon S. Beman in the 1880s for workers at the Pullman railcar factory—quickly seduced them. As did, most likely, the prospect of owning one of those landmark buildings for relatively little money: A renovated one can be had for $250,000, an unimproved one for much less. But it’s the sense of cohesion and intimacy in the neighborhood that keeps residents rooted there. “Pullman is a small but vibrant community where you can really make your mark,” Kaulig says. The entire area was designated a national monument in 2015, drawing new investment from the National Park Service.
In the Suburbs
In an ad campaign designed to attract city-dwelling millennials, Berwyn describes itself as “nothing like a suburb.” Buyers will judge for themselves, but this town’s proximity to the Loop—which lies just 10 miles east—and concentration of Chicago-style bungalows certainly bolster the argument, as does the buzzing street life along Roosevelt Road, home to the celebrated music venue FitzGerald’s and the critically acclaimed restaurant Autre Monde. The giveaway that you’re not in the city? The prices of those bungalows, many of which go for less than $250,000.
Walking through downtown Woodstock is like stepping back in time, what with the small shops occupying ornate 19th-century buildings around a quaint town square. Many residents of this far-flung northwest suburb say they’ve happily accepted a longer commute (a 90-minute drive to the Loop) for a lifestyle that feels more like small-town America than suburbia. “We don’t always attract the chain stores you see in other suburbs, which allows small-business owners to thrive,” says Krista Coltrin, the town’s economic development coordinator. Woodstock is a rarity in the Chicago area in another crucial way: In 2017 the median sale price of a home here was a mere $202,000, making it an affordable option for working families seeking to buy their own house in a safe, vibrant community.
Up to $400,000
Sleek condos blocks from the Loop, a riverside art scene, prewar beauty in a revitalized North Side nabe
In the City
A budget of $400,000 can go a long way in this South Side neighborhood, a hub for Chicago’s Irish community. Think bungalows, Tudors, and colonials with yards big enough for entertaining. Beverly also features a robust art scene—anchored by the 40,000-square-foot Beverly Arts Center—and active civic groups. Many residents tout its sense of stability, thanks to large numbers of multigenerational families. “Beverly has a small-town feel,” says Susan Flood of the Beverly Area Planning Association. “And that’s what keeps people here and brings them back when they’re ready to settle down.”
Given the Loop’s ever-growing global stature, buyers might be forgiven for believing they can’t get anywhere near the city’s humming heart for under $400,000. But while the West Loop and Streeterville have mostly shed their affordable inventory, the South Loop is still a wide-open market in this price range, thanks to ambitious high-rise developments and loft conversions that have transformed historic areas like Printers Row and the Prairie Avenue Historic District into dynamic residential corridors. More change is on the way, in the form of new buildings from big architects—including a 76-story tower by Rafael Viñoly.
With residential lakefront towers, cozy blocks of prewar apartment buildings, and a rich mix of artists, students, professionals, and recent immigrants, Uptown is one of the North Side’s densest and most diverse communities. It’s also one of the most affordable. Those seeking a two-bedroom condo in a vintage building will find plenty of options below $300,000, but by edging up to $400,000, buyers open the field to properties with updated finishes, in-unit laundry, and off-street parking. Recent upgrades along the Red Line—including the $203 million renovation of the Wilson Avenue stop—augur well for growth.
In the Suburbs
Prices in this western suburb have enjoyed a slow, steady climb in recent years, making it the rare market that promises continued growth but hasn’t become overly competitive for buyers. “I hear about people who are hunting for months, but it was easy for us,” says buyer Joe Erbentraut. “It was amazing to see what the same dollar could buy compared to Chicago.” To wit: A classic ranch home can be found in the mid-$300,000s. Add to that the cachet this Fox River town has been stealthily gaining among millennials in the creative fields, many of whom congregate at Water Street Studios, a gallery space near the river.
“You can find very similar homes to those in Beverly but at a much lower price point,” says Redfin broker and Flossmoor resident Andrea Smith Jiles of this quiet southwest suburb. The tradeoff, she says, is the high property taxes, especially for newer homes. Still, with a historic one-block main street, a craft brewery, several country clubs (a legacy of Flossmoor’s former role as a summer getaway for industrialists), and the Metra running through the middle of town—an amenity that has attracted University of Chicago staffers, who like being able to zip to Hyde Park in just 40 minutes—Flossmoor delivers considerable bang for the buck.
Up to $600,000
Lush landscapes, vibrant street life, sparkling new homes
In the City
Old Irving Park
Known for its distinguished Victorians set on large lots, this Northwest Side neighborhood has witnessed a wave of single-family home construction that is helping to lure young families who are seeking more space but aren’t ready to give up city life. With recent sales ranging between $500,000 and $600,000, many of the new houses, such as the small, crisply modern custom-built ones found in the Basecamp SFH development along Milwaukee Avenue, are priced less than comparable new construction elsewhere along the Blue Line. Buyers set on the charm of vintage homes have plenty of options, too—particularly in the Villa, a landmark district of more than a hundred prewar houses and small apartment buildings. Easy access to the Kennedy Expressway, Blue Line, and Metra, as well as proximity to the burgeoning drinking and dining scenes of Avondale, Logan Square, and Portage Park, add to Old Irving Park’s appeal.
In case you haven’t noticed the construction cranes and excavators, the West Loop is a mini-boomtown, with investors pouring hundreds of millions of dollars into the neighborhood in recent years, transforming meatpacking facilities into gleaming tech offices, upscale storefronts, and sleek residential lofts. What was once a gritty backwater is now home to Google, McDonald’s, SRAM, and more than a dozen of the city’s top-tier restaurants. Construction doesn’t appear to be slowing down anytime soon, and that’s kept pockets of this white-hot market surprisingly affordable for condo buyers in the $400,000-to-$600,000 range—especially those who are ready to make the leap quickly, because demand, and prices, are likely to keep going up for the foreseeable future.
In the Suburbs
Lovingly restoring a prewar house is nice, but vintage charm can get expensive, and not everyone values it over a heated three-car garage and gleaming chef’s kitchen. Buyers seeking lots of options for spacious new single-family homes with modern floor plans and up-to-the-minute amenities will find abundance, if not a great deal of variety, in this south suburb. They’ll just have to get ready for some competition. “When an updated house hits the market [in Lemont], there will definitely be multiple offers,” says Redfin agent Andrea Smith Jiles, who focuses on the south suburbs. “I have clients who are on their fifth attempt at buying a place there.”
With its 19th-century homes, lushly landscaped outdoor spaces, and gracefully curving streets, this western suburb literally feels off the grid. This was no accident: The village was planned in 1869 by Frederick Law Olmsted, the renowned landscape architect behind New York City’s Central Park and Chicago’s Jackson and Washington parks. But what makes this suburb most special for prospective buyers is how much architectural interest and beauty you can get for less than $600,000 without having to undertake major renovations or updates.
Up to $800,000
Classic two-flats, horse-country charm, city-adjacent homes in an architectural mecca
In the City
The workers’ cottage was once the backbone of this neighborhood’s housing stock, but you won’t find many left in the former Polish enclave just west of the Kennedy. What you will find, if you’ve got $600,000 to $800,000 to spend, is tremendous value in much of the new construction that’s changed the tenor of the area so dramatically. Upscale finishes, open floor plans, energy-efficient building materials, smart-home automation—such features come standard in many of the condos on the market in Noble Square. A planned overhaul of the old Polonia Triangle at the Ashland, Milwaukee, and Division intersection is expected to breathe new life into the area, with spaces for outdoor vendors, live performances, and dining. The Blue Line runs underfoot, and that not-so-distant roar you hear? That’s your easy expressway dash to downtown or O’Hare.
Many young buyers eye this venerable North Side neighborhood’s abundance of condos priced below $300,000, but arguably the best value is to be found in the area’s classic brick and limestone two-flats, which can deliver impressive space and aesthetic appeal for under $800,000. While Ravenswood is witnessing a steady flow of development, it’s a fairly controlled growth, driven less by speculators than by investors looking to stay put, says resident Phil Thompson. “It feels like a lot’s happening in a quiet way, in contrast to the white heat that Logan Square gives off.” Brown Line access and thriving shops and cultural institutions along Lincoln Avenue, including the Old Town School of Folk Music, have turned the area into a citywide destination. And multiple craft brewery openings have earned a swath of Ravenswood the moniker Malt Row.
In the Suburbs
With its horse farms and forest preserves, Barrington Hills is one of suburban Chicago’s more bucolic places to live. And unlike the neighboring communities that also include Barrington in their names, this one has a law meant to keep things that way: A zoning regulation mandates that residential properties occupy at least five acres. Village president Martin McLaughlin says the ordinance is part of a town code that favors individual property rights. “You can land a hot air balloon on your property, you can raise goats, ducks, chickens, bees,” he says. “The things you can do here, you can’t do in Hinsdale.” Houses on the market—which weathered the Great Recession better than the McMansion-filled communities nearby—tend to be spacious yet relatively affordable: A 3,000-square-foot colonial on seven acres just sold for around $725,000.
Recent high-rise developments near Green Line stations have brought lots of density and new businesses to this near west suburb. But if you get off the main commercial strips, Oak Park’s leafy, inviting blocks—which have long made the town a go-to destination for city dwellers who don’t want to move too far for space, great schools, and a little peace and quiet—feel largely untouched by all the buzz. Buyers willing to spend up to $800,000—along with, it must be said, more set aside for the town’s notoriously steep property taxes—can still easily tap into that appeal, snagging a move-in-ready house with plenty of prewar charm. And while you have little chance of finding one of the town’s 20-plus Frank Lloyd Wright houses among the listings, it’s awfully nice to walk by them on your way to the post office.
View the photo gallery below for details on real estate located in these neighborhoods.
Up to $1 Million
Stellar views of downtown, landmark gems on the South Side, urban energy in a lakeside suburb
In the City
What can a million dollars get you in Chicago’s most exclusive neighborhood? It’s not quite enough to purchase one of the Gold Coast’s coveted graystones, but it can buy you an exceptionally spacious high-rise condo with a much better view. The options in this price range are surprisingly numerous—think three bedrooms with updated finishes in a doorman building along Astor Street or State Parkway. Be warned, though: Monthly assessments in co-op buildings can run upward of $7,000.
Hyde Park and Kenwood
“People are tearing down $2 million houses in Lincoln Park to build bigger ones, but that doesn’t happen here,” says Susan O’Connor Davis, a KoenigRubloff agent and author of Chicago’s Historic Hyde Park. “Residents fought hard to get landmark status.” This accounts in part for the understated majesty of so many blocks in these adjacent South Side neighborhoods, home to the University of Chicago and its acclaimed cultural institutions. Architectural interest seemingly pops up around every corner, from impeccably restored Victorians to bold modernist experiments. Kenwood in particular is known for its fine mansions, and while $1 million isn’t typically enough to snag one, it will easily get you a plenty spacious prewar house on an attractive block.
In the Suburbs
A dense commercial core, clusters of high-rises, a university campus, and multiple CTA stations make this near north suburb feel like an extension of the city. But with its inviting beaches and its dignified old houses, Evanston also carries a whiff of the upscale North Shore. While properties here cover a vast price range, from $200,000 condos near the Chicago city line to multimillion-dollar mansions farther north, the sweet spot hovers just under $1 million, which is enough to buy a recently renovated five- to six-bedroom house with plenty of architectural interest, or even a nicely restored two flat that can generate rental income.
Sky’s the Limit
A modern-day Versailles, tony townhouses, gated estates with private beaches
In the City
Burling, Orchard, and Howe Streets in Lincoln Park
The blocks of these three shady streets south of Armitage Avenue harbor some of the priciest residential properties in the Midwest. In the past three years, 10 homes in this pocket have sold for over $4 million, with the most expensive topping out at $13.3 million. Part of what’s attractive to wealthy buyers, says Jennifer Ames, a broker with Coldwell Banker, is that zoning in this part of Lincoln Park allows owners of multiple lots to demolish existing properties and create much larger homes—like the $50 million manse on Burling that’s currently Chicago’s most expensive residential listing.
In the Suburbs
The Lakefront in Lake Forest and Highland Park
It’s an inescapable truth about waterfront real estate, says luxury broker Ames: “There’s never going to be any more shoreline.” That’s why developers often seek to maximize potential by dividing up properties into ever-narrower parcels. It’s also why wealthy buyers seek out stretches of beachfront like those in Lake Forest and Highland Park, where mansions on large lake-facing lots still come on the market. Another bonus for those seeking exclusivity: the possibility of having a private beach. Unlike in some towns, these two don’t require public waterfront access on private properties.