Bennett Park in Streeterville
Bennett Park in Streeterville Photograph: George Rose/Getty Images


Western Suburbs

The 40 or so green spaces meticulously maintained by the St. Charles Park District provide the setting for a robust array of recreational activities, from swimming to nature walks to skateboarding. Residents take particular pride in the string of greenswards that hug the banks of the Fox River. In Mount St. Mary Park, brick paths wind past flower gardens and tennis courts, converging at a decorative wall on which sits, fittingly enough, a sculpture of Humpty Dumpty. On the river’s east side, Pottawatomie Park offers volleyball, mini golf, and beautiful river views. You can snag a townhome near this pretty stretch of central St. Charles for $350,000, says Suzy Macino of @Properties, and if you want to spend more, sellers in this pricey suburb will oblige. “There’s everything from little 800-square-foot homes to 7,000 square feet. It’s very eclectic.”

St. Charles home
$520,000, 311 Brownstone Dr., 3 bedrooms, 2,400 sq. ft. Photograph: Ryan Lynch/Creative Light Studios


Residents of this high-rise enclave have traditionally had to settle for a trip to the lakefront for their dose of fresh air. That changed in 2019, when the developer Related Midwest transformed two acres of Streeterville into a dynamic public green space that is becoming a downtown destination in its own right. Designed by the creator of Maggie Daley Park and the 606, Bennett Park is adjacent to the developer’s 66-story residential tower, One Bennett Park. The park has a fairyland feel, centered on a “lawn bowl” and encompassing play huts, sandboxes, walking paths, and two dog runs. Uneven demand downtown means you can snap up a bargain in a Streeterville high-rise. “You can negotiate much more than you ever could,” says broker Melanie Everett. The ultraluxe condos in One Bennett start at $1.8 million, but a couple of blocks away you’ll find fully updated units starting at around $250,000.

Streeterville home
$1,975,000 (sold), 1 Bennett Park, 3 bedrooms, 2,100 sq. ft. Photograph: Related Midwest

South Side

With construction set to begin this year on the Obama Presidential Center, all eyes will be on Woodlawn, the neighborhood extending west from the lush expanse of Jackson Park, home to the new center and, as any armchair historian will tell you, site of the World’s Columbian Exposition of 1893. The 550-acre Olmsted & Vaux–designed park and its pleasures — a Japanese garden, sports facilities, a restored prairie habitat, a boat harbor, blossoming cherry trees — are the heart and soul of this neighborhood. Median sale prices for both houses and condos have risen steadily over the past few years, a trend that promises to continue, but there’s still immense value to be found. A completely new, ultramodern three-bedroom townhouse with heated concrete floors and just a few blocks from the park was recently listed for $638,000.

Woodlawn home
$389,000, 1437 E 65th Pl., Unit 1, 5 bedrooms, 3,000 sq. ft. Photograph: Naja Morris/@properties

North Shore

This dense lakeshore suburb is blessed with an impressive 76 parks and 50 playgrounds. The primacy the town places on park access is exemplified by Noah’s Playground for Everyone, which was designed in consultation with pediatric therapists and is fully wheelchair accessible, from the water fountains to the sandbox. Parks have special value for newcomers, who will find fewer housing options close to the waterfront. “Evanston is a very old town, so there’s not a whole lot of new construction right by the lake,” says @Properties broker Allyn Rawling. Head a few blocks in, though, and you’ll find all kinds of options. Just $225,000 will get you a toehold, in the form of a one-bedroom condo within walking distance of any number of parks and playgrounds. A modest house, even one well in from the lake, will run you closer to $1 million.

Evanston home
$179,000 (sold), 817 Forest Ave., 1 bedroom, 800 sq. ft. Photograph: Sandy Sherwood/@Properties
Top: Palos Park Woods in Palos Park; Bottom: Herrick Lake Forest Preserve in Wheaton
From top: Palos Park Woods in Palos Park; Herrick Lake Forest Preserve in Wheaton Photography: (Palos Park Woods) Zbigniew Bzdak/Chicago Tribune; (Herrick Lake Forest Preserve) Courtesy of Forest Preserve District of DuPage County


Northern Suburbs

Many visitors to Glenview pass through town along the main arteries, noticing little more than the shopping strips and gleaming commercial parks. But this suburb is flanked to the east and west by a largely contiguous network of forest preserves that makes the town an excellent access point for some of the metro area’s best walking and biking trails — including the 20-mile North Branch Trail and the 30-mile Des Plaines River Trail. The median sale price of a house in Glenview in 2020 was around $600,000, a lot less than in adjacent Northfield, which boasts a tonier reputation but has way less inventory (99 sales in 2020 versus more than 600 in Glenview).

$495,000, 4676 Jenna Rd., 3 bedrooms, 3,000 sq. ft.
$495,000, 4676 Jenna Rd., 3 bedrooms, 3,000 sq. ft. Photograph: Shirley Faucett/Baird Warner Libertyville

Far Northwest Side

Although Forest Glen is just 10 miles from the Loop, it seems a world away. The aptly named community area, which includes the staid neighborhoods of Edgebrook and Sauganash, extends along a corridor of woodlands encompassing floodplain forests, flatwoods, and open savanna and oak forest. Picnic groves, activity areas, a warming shelter, a sledding hill, a biking trail — all these lie a short walk from virtually any point in Forest Glen. The area consists mostly of single-family homes — midcentury ranches, brick bungalows, English Tudors — giving it a suburban feel. With a median sale price in 2020 of $460,000, those homes are accessible to urban buyers who’d be relegated to condos in many other similarly attractive North Side nabes.

$849,000, 6300 N. Louise Ave., 6 bedrooms, 3,200 sq. ft.
$849,000, 6300 N. Louise Ave., 6 bedrooms, 3,200 sq. ft. Photograph: VHT Studios

Western Suburbs

Walk in virtually any direction from the center of this suburb of 53,000 people and you’ll end up in a forest preserve or leafy public green space. To the west is Cantigny Park, with its flower gardens and shaded picnic areas; to the north, Lincoln Marsh Natural Area, with its lush wetland habitats; and to the south, the 887-acre Herrick Lake Forest Preserve, which is justifiably one of the Chicago area’s most popular preserves, with more than seven miles of trails, including a section of the gorgeous Danada-Herrick Lake Regional Trail. With a median sale price in 2020 of just $380,000 for single-family homes — $75,000 less than in adjacent Naperville — Wheaton offers entry points for new homeowners or budget-minded city dwellers looking to make a break for the suburbs.

$304,000, 407 S. Morgan Ave., 3 bedrooms, 1,300 sq. ft.
$305,000, 407 S. Morgan Ave., 3 bedrooms, 1,300 sq. ft. Photograph: Sara Nader/Redfin

Southwest Suburbs

Well known for the lush forest trails and nature areas that partially surround it — all part of the 15,000-acre Palos Park Woods, the crown jewel of the Cook County forest preserve system — Palos Park is a happy hunting ground for homebuyers with the resources to go big. The homes here have been a magnet for more seasoned buyers who are ready to upsize. Be prepared to spend, says John Schaefer, manager of RE/Max Synergy in nearby Orland Park, but also expect a lot for your money: “There wasn’t a builder who came here and just put in big subdivisions. Mostly everything is custom-built.” That means lots of three- and even four-car garages, among other high-end amenities, and prices hovering around $700,000 for a fully updated three-bedroom, four-bath home — all of it within walking distance of the biggest preserve in the Cook County system.

$750,000, 12813 S. Misty Harbour Ln., 4 bedrooms, 6,800 sq. ft.
$750,000, 12813 S. Misty Harbour Ln., 4 bedrooms, 6,800 sq. ft. Photograph: VHT Studios
The Silver Lake Country Club in Orland Park
The Silver Lake Country Club in Orland Park Photograph: Troy Walsh/Drone Media Chicago


Southwest Suburbs

It’s emblazoned right there on the town’s water tower: “World’s Golf Center.” Other golf-centric cities around the globe might quibble, but it can’t be denied that duffers in this suburb have extraordinary choice, with at least 12 courses within an easy drive of downtown. One of the most popular is the sprawling 45-hole Silver Lake Country Club, which encompasses three individual courses, each presenting distinct challenges. The median single-family home price in town has been creeping up, but the growth hasn’t been explosive — 18 percent over the past five years — and there is plenty of value to be found, whether you’re in the market for a condo (ones in the Fountain Hills development start in the $170s) or a house ($210,000 will get you a 1,000-square-foot two-bedroom). Got the budget to spend big, Tiger? For $1.4 million, you can have three floors, 10,000 square feet of living space, and a four-car garage — plenty of room for an extra set of clubs.

$779,000, 10840 Somer Ln., 5 bedrooms, 4,100 sq. ft.
$779,000, 10840 Somer Ln., 5 bedrooms, 4,100 sq. ft. Photograph: Aryn Van Dyke/United Real Estate

North Suburbs

This affluent village and its adjacent suburbs are home to half a dozen public and private courses. Arguably the most prestigious of them is the Wynstone, a Jack Nicklaus–designed course anchoring a gated residential enclave spread across 750 acres of partially wooded, lake-dotted land. Houses currently on the market within the community range from around $500,000 for a 3,800-square-foot three-bedroom to $1.7 million for a six-bedroom manse — competitive prices relative to the surrounding area. Purchasing any of those homes requires becoming a dues-paying member of the Wynstone Property Owners’ Association, whose fees can run to nearly $6,000 annually. That said, the association takes care of pretty much everything, from landscaping and water treatment to 24-hour private security.

$1,199,000, 56 S. Wynstone Dr., 5 bedrooms, 6,600 sq. ft.
$1,199,000, 56 S. Wynstone Dr., 5 bedrooms, 6,600 sq. ft. Photograph: Kelvin Lin/VHT Studios

Northwest Suburbs

Created by the environmentally minded course designer Rick Jacobson, the award-winning links at Bowes Creek Country Club, on the western fringe of this handsome Fox River town, are open to the public but offer dues-paying members perks like free use of golf carts and priority tee times — which visitors can get a taste of thanks to the club’s “member for a day” passes, starting at $90. The developer Toll Brothers is building several dozen smartly appointed open-concept single-family homes on lots facing the fairways, all with access not just to the nearby club but also to walking trails and playgrounds. The new houses start at around $390,000 — a price point comparable to what you’ll find for existing construction elsewhere in town.

$473,000, Bowes Creek Country Club Fairways Collection (model shown), 3 bedrooms, 2,300 sq. ft.
$473,000, Bowes Creek Country Club Fairways Collection (model shown), 3 bedrooms, 2,300 sq. ft. Photograph: WayUp Media
The Jeanne Gang–designed Eleanor Boathouse in Bridgeport
The Jeanne Gang–designed Eleanor Boathouse in Bridgeport Photograph: SteveHall/Studio Gang


Western Suburbs

Naperville’s Riverwalk may not be as famous as Chicago’s, but it’s a lot less hectic, located along a gentle bend in the DuPage River and graced with brick-paved paths, fountains, a footbridge, and sculptures. “The Riverwalk area is a huge asset, kind of a model for what a riverwalk should be,” says Eric Rogers, a Century 21 Affiliated broker. One advantage of living near it is that you’re also downtown, putting you steps from the Naperville’s historic district and top-notch dining and drinking, including the vaunted high-end coffee purveyor Sparrow, which is a block from the river. Given the enormous inventory in this burgeoning burb — it logged more than 2,000 sales in 2020 — there’s a price point for every budget. A downtown two-bedroom condo will run you about $300,000. For the best value, Rogers recommends looking at new developments south of downtown.

$529,000, 427 W. Jefferson Ave., 3 bedrooms, 2,200 sq. ft.
$529,000, 427 W. Jefferson Ave., 3 bedrooms, 2,200 sq. ft. Photograph: Leslie Lemmons


The commercial heart of this downtown community area includes the Mag Mile’s upscale shops and restaurants. But arguably of more value to residents is the fact that the area’s southern boundary is the Chicago River itself, specifically the stretch occupied by the Riverwalk, with its packed cafés, brewpubs, and eateries — all of which are rightly held up as the prime symbol of the river’s years-in-the-making rehabilitation. While farther-flung city nabes and suburbs are currently seeing bidding wars and crowded open houses, much of the Near North Side is “100 percent a buyer’s market,” according to broker Melanie Everett, with fully updated condos in a river-adjacent building like the Park Place, on Kingsbury Street, starting at under $300,000. “There is an opportunity to scoop something up at a really great price in an awesome location.”

$529,000, 427 W. Jefferson Ave., 3 bedrooms, 2,200 sq. ft.
$529,000, 427 W. Jefferson Ave., 3 bedrooms, 2,200 sq. ft. Photograph: Leslie Lemmons

Western Suburbs

Many Chicagoans looking west to buy tend to focus on the more upscale Fox River enclaves of Geneva and Batavia, but that’s changing, says broker Linda Pilmer: “People from Chicago have been moving to Aurora because of affordable prices.” Indeed, with its historic downtown and the expansive neighborhoods of handsome prewar houses on its west side — including one designed by Frank Lloyd Wright — Aurora offers exceptional value for the money. A two-bedroom riverfront condo can be had for about $225,000. Aurora also offers access to the Fox River Trail, a 40-mile paved biking and walking route.

$290,000, 430 Grand Ave., 6 bedrooms, 3,300 sq. ft.
$290,000, 430 Grand Ave., 6 bedrooms, 3,300 sq. ft. Photograph: Dickerson Team

South Side

When most people think of recreation on the Chicago River, their thoughts turn to downtown, with its Riverwalk and boat tours, or to neighborhoods along the North Branch like Lincoln Square. But developers are betting big farther south, in Bridgeport, where new townhomes are going up along the South Branch, many just steps from the prosaically named Park No. 571. That 4.5-acre riverfront jewel is home to a boat launch and a Jeanne Gang–designed boathouse, which has a training facility for rowing teams, as well as kayak storage and exercise areas. A sextet of river-accessible townhouses from the Hulett Group each have a private roof deck and start at just under $700,000. Buyers with smaller budgets can find relative bargains in the form of fixer-upper houses just a few blocks in from the river.

$689,000, 2825 S. Short St., 5 bedrooms, 3,700 sq. ft.
$689,000, 2825 S. Short St., 5 bedrooms, 3,700 sq. ft. Photograph: Sherry Ng/Goodland Realty
Top: The South Shore Cultural Center, at lower right; Bottom: Rosewood Beach in Highland Park
From top: The South Shore Cultural Center (seen at lower right); Rosewood Beach in Highland Park Photography: (South Shore Cultural Center) Alex Garcia/Chicago Tribune; (Rosewood Beach) Chris Walker/Chicago Tribune


Far North Side

While famously expensive Lincoln Park and its eponymous waterfront stomping ground attract huge summer crowds seeking water and waves, this quieter, stately North Side enclave offers city dwellers something more rarefied: close-to-the-beach prewar homes at not-exorbitant prices. “There are little pockets of Edgewater such as Edgewater Glen, which are within walking distance to the lake,” says Debi Weinberg of @Properties. “Most of the homes there tend to be older and many of them are updated. It’s more affordable to get a single-family home there than, say, in Lincoln Park or Lake View.” Handsome older houses can also be found in Lakewood Balmoral, a historic district within Edgewater, many of them undergoing gut renovations and selling for north of $1 million — but a lot less than comparable homes in Lincoln Park — with unrenovated properties considerably cheaper.

North Side

If there is a single spot that captures the manifold glories of Chicago in the summertime, it’s Belmont Harbor. Bustling with recreational boaters, kids taking sailing lessons, tennis players, cyclists, nature lovers visiting the migratory bird sanctuary, and even golfers, this stretch of lakefront can feel like the center of the universe on a nice day. The dense residential neighborhood west of the harbor offers surprisingly affordable options, especially for young first-time homebuyers. “Studio apartments and one-bedroom units in a high-rise can be purchased for under $200,000,” says Lyle Harlow, managing broker of Kale Realty. And with the Red Line running through the heart of the area, and Lake Shore Drive just blocks away, Lake View delivers unsurpassed access to the city beyond the harbor — if you ever have the urge to leave.

$290,000 (sold), 1140 W. Wellington Ave., 2 bedrooms, 750 sq. ft.
$290,000 (sold), 1140 W. Wellington Ave., 2 bedrooms, 750 sq. ft. Photograph: Brent Borchardt/Melanie Everett & Company

North Shore

Almost 10 percent of Illinois’s Lake Michigan shoreline falls within the bounds of this leafy suburb, which boasts no fewer than four public beaches, as well as boat launches and pretty bluff-top parks. Those assets don’t come cheap: Single-family homes on the water start at $3 million, with one recently fetching close to $15 million, and unlike in the city, there aren’t any shorefront condo buildings. But if you’re willing to tote your towel a few blocks, the options expand: Condo developments close to the main drag of Green Bay Road are offering units in the $400,000 to $850,000 range — and what they lack in instant access to the water, they make up for in proximity to shops and restaurants. Demand for such properties has soared, says Beth Alberts of Compass. “People who are used to living in the city like to be in a walkable town.”

$845,000, 1789 Green Bay Rd., 3 bedrooms, 2,600 sq. ft.
$845,000, 1789 Green Bay Rd., 3 bedrooms, 2,600 sq. ft. Photograph: VHT Studios

North Shore

This lakefront village of 8,900 doesn’t boast the abundant beaches of Highland Park, just to the north — Glencoe has a single, very nice public swimming beach — but it has something Highland Park doesn’t: an incredible backyard. The town’s entire western border abuts the bucolic Skokie Lagoons, with its ponds and walking trails, and the magnificent Chicago Botanic Garden. What’s more, Glencoe, virtually all of which lies within walking distance of the beach, offers a remarkable amount of choice for its size when it comes to housing. Homes run the gamut from two-story Tudors to vintage colonials, as well as townhomes, which can be had for as little as $370,000 — all of it giving the suburb a diverse, colorful character. “It’s a family community that’s really charming,” says Jenni Gordon, a broker for Matlin Group of Compass, “but it’s not a subdivision type of place.”

$875,000, 362 South Ave., 5 bedrooms, 4,200 sq. ft.
$875,000, 362 South Ave., 5 bedrooms, 4,200 sq. ft. Photograph: Mac DuBose/Coldwell Banker Winnetka

South Side

On a fine summer day, the broad crescent of Rainbow Beach feels like the thumping heart of the South Side, with hundreds of sun seekers and families arrayed across the sand and boats from Jackson Park’s nearby harbor bobbing in the waves. The neighborhood just to the west of the beach is justly proud of its waterfront — and of its architecture, too: Few lakeside communities pack in as much architectural interest as South Shore, from the six graceful 1920s apartment buildings of the Jeffrey-Cyril Historic District to the Mediterranean grandeur of the South Shore Cultural Center to the distinctive 19th-century colonial and Renaissance revival homes of the Jackson Park Highlands area. “You are going to see a lot of historic homes, a lot of mosaic tiles, a lot of different woods— everything about these homes screams character,” says Coldwell Banker’s Mara Morris of that elegant enclave. A fully renovated, century-old five-bedroom home there was recently listed for $390,000, which would get you a modest condo in many North Side lakefront nabes.

$390,000 (sold), 7027 S. Constance Ave., 5 bedrooms, 2,000 sq. ft.
$390,000 (sold), 7027 S. Constance Ave., 5 bedrooms, 2,000 sq. ft. Photograph: @properties Goose Island