The Best Places to Live

Housing prices have cooled, but inventory is still down. Here’s where to find the home you need, whatever your situation.

June 6, 2023, 8:14 am

Starter Searchers

You’re ready to stop paying rent and begin planting roots within the city limits, but you’re on a budget.

$335,000 (sold) | 1730 S. Desplaines St., Pilsen, 3 bedrooms, 1,900 sq. ft.
Photo: Realvision

West SidePilsen

Median sale price: $395,000 (condos/townhomes)
Five-year change: 43%

Though prices for condos in the Lower West Side as a whole have been escalating, Pilsen is “still cheaper relative to other areas,” says Tim Kavanaugh of eXp Realty. He points to recent development along 18th Street that is particularly promising for first-time buyers who don’t need all the amenities that come with high-rise living. “A lot of the buildings are three to six units,” Kavanaugh says. “They’re going to have a smaller feel compared to a Gold Coast skyscraper.” They’re also going to have a smaller price tag : A two-bed, two-bath condo listed at $319,000 this spring had monthly HOA fees of just $200. And in Pilsen, you won’t need all the in-house perks that come with a higher assessment: Within blocks, raise a glass at Simone’s, nosh at Michelin-starred Dusek’s, and catch top bands at Thalia Hall.

$275,000 (sold) | 4111 N. Kenmore Ave., Buena Park, 2 bedrooms, 1,350 sq. ft.
Photo: Mark Winkelman

North SideBuena Park

Median sale price: $305,000 (condos/townhomes)
Five-year change: 23%

Love the lakefront? Then you’ll adore Buena Park, which Nitasha Kassam of @properties Christie’s International Real Estate believes many buyers overlook: “There is some really good inventory where you can find one- and two-bedroom condos at a decent price point with assessments that won’t break your bank.” To keep those fees in check, steer clear of the high-rises right along the water and look instead at smaller walkup buildings on quiet streets not named Marine Drive. Take the two-bed, two-bath condo on Cuyler Avenue that sold for $374,000 this spring, with HOA fees just over $300. That unit included a heated garage spot and a 20-by-9-foot patio. The neighborhood is quieter than bordering Wrigleyville and Uptown, yet you won’t have to walk far for local staples like the cozy bistro-pub Bar on Buena or the Venezuelan bakery Klein’s.

Southwest SideBeverly

Median sale price: $393,000
Five-year change: 34%

No block looks identical in this part of town, home to the South Side Irish Parade and the annual Beverly Art Walk. “Beverly has a lot of unique properties,” eXp Realty’s Kavanaugh says. “It’s not like a subdivider came in and started cranking out homes. There’s a real architectural charm there.” While Kavanaugh warns that houses in West Beverly, with their larger lots, tend to be more expensive, there are still deals under $400,000 as you get closer to Beverly Boulevard. A two-bed, one-bath rehabbed Georgian recently listed for $329,000 — less than a 10-minute walk from the 99th Street Metra station, one of the neighborhood’s five stops along the Rock Island line.

Photo: Bruce Leighty/Getty Images

Northwest SidePortage Park

Median sale prices: $400,000; $159,000 (condos/townhomes)
Five-year change: 29%; 3%

Prices have skyrocketed in Avondale, but there are relative bargains a few blocks northwest in Portage Park. If you’re looking for a standard two-bed condo, you’ll find plenty of options below $200,000. On a bigger budget? You can score a three-bed, one-bath brick bungalow listed for under $400,000 five blocks north of the actual 38-acre Portage Park. This neighborhood is rich in bungalows, whose floor plans maximize your living space, giving you room to grow, says Mike Opyd of RE/Max Next: “Although some people don’t like bungalows, that’s exactly the purpose for them.”


Perhaps you don’t want to deal with wiring that looks like it was part of a 1920s science experiment, or maybe you just want central air. Bottom line: “Vintage charm” has lost its charm.

$579,000 (contingent) | 6332 S. Champlain Ave., Woodlawn, 5 bedrooms, 3,050 sq. ft. lot
Photo: Marni Beals/Exit Strategy Realty

South SideWoodlawn

Median sale prices: $478,500; $230,000 (condos/townhomes)
Five-year change: 242%; 64%

As recently as 2019, 27 percent of lots in this neighborhood were vacant. Today? You’ll find an influx of new buildings like the $800,000 three-flats — three-bed, two-bath units — at West Woodlawn Pointe, perfect if you want to be a landlord that calls one of those floors home and rents out the rest. There has also been notable new single-family home construction. In February, you could get a four-bed, three-and-a-half-bath house, built in 2022, on St. Lawrence Avenue for $515,000. “The price boom in Woodlawn has been astonishing,” says eXp’s Tim Kavanaugh. With the coming of the Obama Presidential Center and the restoration of Jackson Park Golf Course, that will likely continue. But the city has created development stipulations to retain a certain level of affordable housing here.

$695,000 (sold) | 3430 W. Pierce Ave., West Town, 3 bedrooms, 2,630 sq. ft.
Photo: Michael Evangelista

West SideWest Town

Median sale prices: $1.1 million; $512,000 (condos/townhomes)
Five-year change: 17%; 14%

West Town’s Ukrainian Village first saw a run of new construction, and that boom has now spread west to neighboring Humboldt Park. “On the east side of the actual park — especially the stretch that runs east of Kedzie to Western — there are quite a few new multifamily buildings and single-family homes,” says Mike Opyd of RE/Max Next. Across all of West Town, more than 80 properties built within the last five years were for sale this spring. For a new two-bed, two-bath with the shine of waterfall countertops, wide-plank flooring, and high-end appliances, buyers can expect to spend upward of $500,000, Opyd says — slightly less if you are OK with less-refined finishes. There are also larger new single-family homes on the market — a five-bed, three-and-a-half-bath is a common footprint — with the kind of open floor plans parents love, but those push near the $1 million mark and beyond.

$715,000 | 23365 W. Pearson Dr., Plainfield, 4 bedrooms, 3,250 sq. ft.
Photo: Miguel Ramirez

Southwest SuburbsPlainfield

Median sale price: $376,500
Five-year change: 51%

It’s no surprise: The farther you go from the city, the more recent development you’ll find — and Plainfield, a 45-minute drive sans traffic from the Loop, has been making a name for itself as a small town with a big appetite for new construction, following in the footsteps of its northerly neighbor, Naperville. More than 600 permits for single-family homes were issued here in 2020 and 2021, and the village recently approved plans for a development that includes more than 330 single-family properties and 100 townhouses. Homes on lots that cover more than a quarter acre often climb above the $600,000 mark, but there are bargains to be found for other new properties, like the open-floor-plan four-bed, two-and-a-half-bath house decked out with smart home technology that sold for less than $447,000 in April.

Suburban Skeptics

You want to leave the city, but not city living. Yes, you know all about Evanston and Oak Park, but there are other burgs that offer urban energy.

West SuburbsBerwyn

Median sale price: $295,000
Five-year change: 39%

Berwyn is essentially an extension of the city. If you have any doubts about its ability to deliver a nonsleepy lifestyle, just grab a drink at a bar in the Depot District or see a show at FitzGerald’s — home of the American Music Festival, which this summer will feature Lucinda Williams and Steve Earle. There’s also plenty to love about its relatively affordable housing, though some homes may need updating. Nearly 90 percent of single-family listings this spring were at least 50 years old. “These properties are becoming more readily available,” says Megan Rork of Coldwell Banker. “And the prices are approachable for first-time buyers.” If you have more to spend, there are some move-in-ready gems, like a $450,000 four-bed, four-bath gut rehab on Highland Avenue with a finished basement and two-car garage.

$599,700 (contingent) | 808 S. Catherine Ave., La Grange, 4 bedrooms, 1,800 sq. ft.
Photo: Positive Light

Southwest SuburbsLa Grange

Median sale price: $610,000
Five-year change: 20%

You’ll be only a 24-minute Metra ride from Union Station, but you may not feel the urge to go downtown. Wake up early for brunch at Blueberry Hill, enjoy a large pour as a member of the Mug Club at Milk Money Brewing, or grab a table at Prasino, one of the best farm-to-table restaurants in America. La Grange might earn the quaint designation as a “village,” but the vibe is more small city. “If you were to ask what towns can emulate the walkable downtown Chicago lifestyle in the western suburbs, La Grange is a really good bet,” says Jack Brennan of Second City Agents at Compass. A big part of its draw is its historic district, which evokes the curb appeal of a different era. “You have homes from the 1800s and early 1900s with a ton of character and charm,” Brennan says. “Many have been lovingly restored.” It’s not a cheap place to live, but if you don’t need a huge footprint, focus your search south of 47th Street and west of La Grange Road, where you can find three-bedroom properties for under $500,000.

Northwest SuburbsDes Plaines

Median sale price: $350,000
Five-year change: 29%

If you haven’t visited downtown Des Plaines in the past five years, you might not recognize it today. The hallmark of the change is the 97-year-old Des Plaines Theatre, which the city, bolstered with funds from Rivers Casino, spent $8 million to purchase and renovate, outfitting the 1,000-seat performance venue with a Prohibition-style speakeasy and a wood-fired pizza joint. There’s been plenty of development on the residential front, too, such as Halston Market, a community of 125 townhomes equipped with smart home technology and located just a three-minute drive from Lake Opeka. If you’re more into vintage charm, the city has plenty of old-school energy, like a three-bed, three-and-a-half-bath vintage house just half a mile from downtown, listed for $375,000. “Des Plaines is one of those suburbs where you can really get a bang for your buck,” Nitasha Kassam of @properties Christie’s says. “In surrounding suburbs like Skokie, Niles, and Morton Grove, your price point is going to be a lot higher.”

Photo: Thomas’ Photographic

South SuburbsFlossmoor

Median sale price: $327,000
Five-year change: 52%

If you’re a regular at Revolution, Middle Brow, or any of the other renowned beer destinations in Chicago, you’ll want to raise a glass at Flossmoor Station Brewing Company, whose Wooden Hell variation earned RateBeer’s nod for the best beer in Illinois. It’s housed in an old Metra stop — adjacent to today’s station — with a patio that rivals any of Chicago’s best. Then head next door to pick up a soundtrack for your turntable at Conservatory Vintage & Vinyl. But in Flossmoor, it’s not just about places to eat, drink, and shop. “It’s wonderfully diverse and LGBTQEXPAND
friendly — a huge selling point for lots of folks coming out from the city,” says Coldwell Banker’s Rork. While the inventory here is relatively low, keep your eye out for prizes like the three-bed, one-and-a-half-bath Colonial less than a mile from the train station that was recently listed for $285,000.

$615,000 (off market) | 1407 Elmwood Ave., 3 bedrooms, Wilmette, 7,080 sq. ft. lot
Photo: Realvision, Village of Wilmette

North SuburbsWilmette

Median sale price: $903,500
Five-year change: 24%

With neighborhood restaurants like Sophia Steak — from the same group that runs Logan Square’s Andros Taverna — and a soon-to-open Small Cheval (the first-ever outside the city), Wilmette’s downtown has the energy of a mini Lincoln Square. And if you steer clear of the megamansion territory along Sheridan Road, you can find relatively affordable gems. “Wilmette has a big range when it comes to price,” says John Nash of Jameson Sotheby’s International Realty. Buyers can find plenty of three-bedroom properties in the $500,000 to $700,000 range, such as a three-bed, two-and-a-half-bath farmhouse that went on the market in the spring for $629,000. It’s a 10-minute walk to all that downtown fun and across the street from the nine-mile Green Bay Trail, a favorite of local cyclists. Plus, Nash says, there are two- and three-bed condos and townhomes nearby for buyers who don’t need as much space. And if this suburb ever starts to feel, well, too suburban, Chicago is easily accessible via the Metra and the CTA’s Purple Line.

Space Chasers

Whether you’re about to welcome another baby or your aging parents are moving in, you need more square footage, inside and out — at a reasonable cost.

$800,000 (contingent) | 38 Christina Cir., Wheaton, 5 bedrooms, 3,840 sq. ft.
Photo: 1st Look Media

West SuburbsWheaton

Median sale price: $467,000
Five-year change: 22%

You’ll be a bit far out here — 26 miles from downtown Chicago — but the town is soaring in popularity, says eXp Realty’s Tim Kavanaugh. Value is a big reason why. A $500,000 budget can get you a four-bed, two-and-a-half-bath home on a sprawling 1.1-acre lot, including a basketball court. There’s plenty of green space nearby, too, thanks to a 52-park network that covers a total of 800 acres. And if you’ve got more money to spend, there are properties here that rival the luxurious vibe of the North Shore but often with larger lots. One recent listing: a $2.25 million, 5,312-square-foot palace near the Chicago Golf Club on grounds that exceed two acres.

$695,000 (sold) | 3628 Winnetka Rd., Glenview, 4 bedrooms, 2,600 sq. ft.
Photo: VHT Studios

North SuburbsGlenview

Median sale price: $699,000
Five-year change: 29%

Glenview is expensive, to be sure, but it’s easier to find reasonably priced four- and five-bedroom properties here than it is in the lakefront suburbs, says John Nash of Jameson Sotheby’s. Consider the fully upgraded four-bed, two-and-a-half-bath home on Winnetka Road that sold this spring for $650,000 — a relatively reasonable $250 per square foot. Just down the road in Winnetka, a similarly sized home was $337 per square foot. Plus, the annual property taxes on the Glenview property are about $5,000 cheaper. Head closer to the town’s western border with Prospect Heights, and you’ll find the kind of indoor and outdoor footprints that can let you stretch out even more. “It’s not uncommon to find a quarter-acre lot in Glenview,” Nash says.

$872,500 (sold) | 6862 Fieldstone Dr., Burr Ridge, 5 bedrooms, 3,830 sq. ft.
Photo: Cris Cunningham/Portraits of Home

Southwest SuburbsBurr Ridge

Median sale price: $840,000
Five-year change: 21%

This is another burg that’s not cheap, but you get “a lot more for your money in terms of space inside and out,” notes Jack Brennan of Second City Agents. A six-bed, five-bath home that was listed for $860,000 this spring, for instance, boasts 4,553 square feet, a four-car garage, and a full acre lot. The $189-per-square-foot price is good value compared with the $213 you’d pay for a comparable listing five miles north in Hinsdale. Burr Ridge offers the kind of quiet living you’d expect 19 miles southwest of the Loop. Yet the days when residents had to drive to Hinsdale or La Grange for dinner are gone: The Burr Ridge Village Center, built in 2007, features familiar names from the city, like the restaurant and bar Hampton Social and the breakfast joint Yolk.

$719,000 | 5051 W. Balmoral Ave., Forest Glen, 5 bedrooms, 3,450 sq. ft.
Photo: VHT Studios

Northwest SideForest Glen

Median sale price: $530,000
Five-year change: 20%

“More space” and “city living” don’t typically fit in the same sentence, but they coexist in certain sections of this neighborhood. “A couple of my favorite areas [within Forest Glen] are Edgebrook and Sauganash,” says Mike Opyd of RE/Max Next. There, Georgians, Colonials, Victorians, and bungalows offer larger confines. That bigger footprint can extend outside too. Since not every property here sits on the standard 25-by-125-foot city lot, “there’s a lot more flexibility in outdoor space,” says Opyd. “You’re still in the city, but it doesn’t feel like it.” And if you need further breathing room, this part of town is an outdoor enthusiast’s paradise, boasting the nature preserves of LaBagh Woods and Sidney Yates Flatwoods.


Outdated kitchen, flood-damaged basement, a roof in disrepair — you look past that and see new possibilities and a good investment.

South SuburbsLansing

Median sale price: $195,000
Five-year change: 105%

When it comes to speculative real estate investors, Tim Kavanaugh of eXp Realty points most of them to Lansing, 27 miles south of the Loop. “There is a good amount of inventory that might need some work,” he says. More than 70 percent of the homes on the market in this suburb at presstime were at least 50 years old. But that extra work can pay off. Consider the three-bed, one-bath ranch home that sold here for just $28,500 in 2011. After a complete remodel, along with additional cosmetic updates in the kitchen and bathroom earlier this year, the home recently sold for $195,000. According to data from Connected Investors, the median flip profit here is nearly $100,000.

$255,000 | 3329 S. Oakley Ave., McKinley Park, 6 bedrooms, 3,000 sq. ft. lot
Photo: Teresa Zubricki

Southwest SideMcKinley Park

Median sale price: $348,500
Five-year change: 43%

Bridgeport has boomed over the past decade, and its neighbor to the west seems poised to follow suit. “There’s going to be a lot of development happening over the next decade as more developers come in and start tearing stuff down and building up,” Mike Opyd of RE/Max Next says. Before that drives up the prices, now is the time to jump in. Warning: Get ready to roll up your sleeves. Take a three-bedroom home on South Honore Street that recently went on the market. The listing photos show something out of a horror movie, complete with gaping holes in a wall and stains on the floor. Perhaps even scarier: the disclaimer that prospective buyers are responsible for dealing with any city violations. (Quite a few homes here from the late 19th century are listed with similar disclaimers.) But the upside: It was priced at $124,000, leaving room in your budget for both the expected and the unexpected.

$379,900 (sold) | 6538 N. Albany Ave., West Ridge, 3 bedrooms, 1,090 sq. ft.
Photo: Four Daughters Real Estate

North SideWest Ridge

Median sale price: $464,750
Five-year change: 26%

The delicious eats that line Devon Avenue are enough of a reason to put West Ridge on your house-hunting map, but if you have an appetite for building sweat equity, you can find nice deals there. “There aren’t many single-family or townhome properties in West Ridge that go on sale, but when they do, they’re usually fixer-uppers at a lower price point,” says Nitasha Kassam of @properties Christie’s. “You can gut it room by room, and that is going to be a great investment whether you resell it or just keep it.” Consider a recent listing on Mozart Street. Built in 1955, the three-bed, two-bath ranch home with an unfinished basement was in need of a gut rehab, and the buyer was able to snap it up for just $275,000. An extra perk here: By the time you’re done rehabbing, you will have another option for getting around, thanks to the new Peterson Ridge station on Metra’s Union Pacific North Line, which is expected to open this summer.


You’re an empty nester who is done with the hassle of maintaining a house. But while you want the smaller space of a condo, you’re willing to pay for amenities.

$245,000 (sold) | 5801 N. Sheridan Rd., Edgewater, 2 bedrooms, 1,400 sq. ft.
Photo: VHT Studios

North SideEdgewater

Median sale price: $235,750 (condos/townhomes)
Five-year change: 9%

Here you will find buildings that are much older than some of the top spots downtown but with an equally timeless view of Lake Michigan — and a level of affordability that attracts older couples. “You can get a pretty decent unit for $250,000 or less,” says Nitasha Kassam of @properties Christie’s. “The flip side is that the assessments are a bit higher. But if you’re paying cash [for the condo], then the assessment of $900 kind of feels like your rent payment.” And that often comes with some welcome amenities. Take the 22nd-floor one-bed, one-bath on Sheridan Road that sold for $182,000 this spring. With relatively modest HOA fees of $531, you get a 24-hour doorman, tennis courts, and most utilities. In-unit washer and dryers aren’t always available in pre-1970s Edgewater units due to the plumbing, but most of those have a dry cleaner on the ground floor. Let someone else handle your clothes while you play. You’ve earned it.

Photo: Bjarte Rettedal/Getty Images

DowntownThe Loop

Median sale price: $370,000 (condos/townhomes)
Five-year change: 9%

Nathan Binkley of Compass points to the Loop and River North as areas that are “on super sale” after the upheaval of the pandemic and continued eruptions of mayhem. “The two areas are still very undervalued,” he says. For downsizers, focus on the Loop, where you aren’t so close to the din of River North nightlife and where prices actually dipped — by 4 percent — in 2022. In master-planned developments like Lakeshore East and some of the other high-rises along the lakefront, you can enjoy feeling like you’re living in a high-end hotel. A two-bed, two-bath unit at Harbor Point, for instance, sold for $490,000 this spring. The monthly $1,192 HOA fee is certainly eye-popping, but it includes an indoor pool, hot tub, and steam and sauna facilities. Basically, you’re living at the spa. And that’s OK: Retirement should be synonymous with relaxation.

West SuburbsOak Brook

Median sale price: $865,000
Five-year change: 7%

Yes, this tony suburb boasts multimillion-dollar mansions. But there are loads of lower-priced properties that still deliver a high-end experience, like a two-bed, two-bath condo at the Oak Brook Club — a gated community that includes a clubhouse, exercise room, party room, and 25-acre grounds — listed for $600,000 in April. Its monthly HOA fees are in the $1,000 range, but you will save in another way: Oak Brook has the lowest property tax rates in DuPage County — a key selling point for those on a fixed income. Don’t want your downsizing to involve sharing a wall with a neighbor? Jack Brennan of Second City Agents recommends Forest Gate and Briarwood Lakes, both gated 55-plus communities with single-family homes, as good options for those seeking a small footprint but big amenities.