Real estate activity is down and borrowing standards have tightened, but mortgage rates are at near-historic lows. Which means it’s a good time to buy if you know where to look. That’s where we come in.

The First-Timers

You are looking to get some skin in the game by buying a condo.

$449,000 | 758 N. Larrabee St. | 2 bedrooms | 1,600 sq. ft.

Near North SideRiver North

A typical first-time condo buyer has a simple checklist: “nightlife, dining options, and an easy commute,” says @Properties broker Luke Blahnik. By those criteria, River North, which has been experiencing a luxury residential tower boom the past eight years, gets a perfect score. Real estate here isn’t cheap — you won’t find a condo listed under $265,000 at the moment. But if you search between the river to the west and Wells Street to the east, you can find one-bedroom lofts with brick walls and wood beams for just a little bit more than that: from as low as $270,000, which is a steal. (The median price of condos currently listed in River North is $425,000, according to Zillow.) Those units might run small, but what you sacrifice in price per square foot, you gain in convenience to downtown, liveliness, and the knowledge that you just invested in one of the city’s most consistently high-valued neighborhoods.

$289,700 | 1645 W. Ogden Ave. | 1 bedroom | 900 sq. ft.
Photo: Mike Lavelle

West SideNear West Side

The West Loop has soared out of reach for budget-minded buyers, but that’s made adjacent neighborhoods all the more attractive, says Staci Slattery, a managing broker at North Clybourn Group. You can easily find a two-bedroom condo for less than $300,000 once you cross west over Ogden Avenue. “There’s a Pete’s Fresh Market at Madison and Western that was a big game-changer for the area,” Slattery adds. “More of those types of amenities are going to crop up in the neighborhood as people continue to move in.” In fact, right now there’s a two-bed, two-bath condo listed for $199,000 that’s just a six-minute walk from Pete’s.

$145,000 | 708 W. Bittersweet Pl. | 1 bedroom | 550 sq. ft.

North SideUptown

For folks in their 20s and 30s, the proximity to good music (historic venues such as the Aragon, Riviera, and Green Mill) and good food (like the strip dubbed Asia on Argyle) is a big draw. Several buildings in Uptown have recently been rehabbed, including the Lawrence House, and while its units are rentals, “that is making the neighborhood a place where many young buyers want to purchase,” @Properties’ Luke Blahnik explains. But that hasn’t driven prices out of reach — there are more than a dozen studios and one-bedrooms on the market for less than $140,000. And you won’t pay a whole lot more for additional space and lake views: A 1,200-square-footer on the 11th floor of a Marine Drive high-rise is priced at $149,900.

$250,000 | 4218 S. King Dr. | 3 bedrooms | 1,500 sq. ft.

South SideBronzeville

A steady flow of new construction and the addition of a Mariano’s have helped fuel a resurgence in this history-rich neighborhood. The median sale price for townhouses and condos in the Grand Boulevard community area (in which the bulk of the neighborhood is located) jumped from $85,000 in 2014 to $210,000 last year. If that combination of rapid appreciation and still-attainable prices isn’t appealing enough, consider the access to the lakefront (a few blocks from Bronzeville’s border) and public transportation (the Green Line rolls through it), the barbecue and soul food joints (like Honey 1 BBQ and Peach’s), and the monuments to the neighborhood’s black cultural legacy (the Walk of Fame on King Drive honors such former residents as Louis Armstrong, Jesse Owens, and Ida B. Wells).

The New Suburbanites

You’re a city dweller who wants to move to a suburb that still feels like a city.

$385,000 | 844 Maple Ave. | 3 bedrooms | 1,531 sq. ft.

Western SuburbsDowners Grove

Evanston and Oak Park, being adjacent to Chicago, have long attracted urbanites flirting with the idea of suburban living, but more and more such buyers are now looking farther out for better deals. North Clybourn Group’s Staci Slattery just helped one Chicago expat close on a small house in Downers Grove, where for $400,000 you can find 1,500-square-foot single-family homes within walking distance of the Metra (30 minutes to the Loop on an express train) and a local downtown with urbane shops and restaurants (including Anderson’s Bookshop, a bibliophile destination, and Parkers’ Restaurant & Bar, whose offerings have been lauded by Wine Spectator). Another draw: the 50-acre McCollum Park, which has 10 lighted tennis courts, three sand volleyball courts, an 18-hole miniature golf course, a 1.2-mile walking path, and an ice-skating rink in the winter. Call it the burb version of Maggie Daley Park.

$675,000 | 2044 Valor Ct. | 3 bedrooms | 3,650 sq. ft.

Northern SuburbsGlenview

“When I first got in this business, buyers from the city wanted to come to Glenview if they couldn’t afford Wilmette or Winnetka,” says Coldwell Banker’s Anne DuBray. “Now many come directly to Glenview.” Check out the Glen, a development on a former naval air station that has 2,300 residential units (a mix of single-family homes, townhouses, condos, rentals, and senior housing), businesses (including a cooking school and an ArcLight theater), its own Metra station, and a 142-acre park. You can get a 1,500-square-feet townhouse for as low as $375,000 or more than double that space for an extra $300,000 (like the one pictured above).

$450,000 | 134 Columbia Ave. | 3 bedrooms | 1,602 sq. ft.

Western SuburbsElmhurst

This is one of the most buzzed-about destinations among city dwellers looking to make the leap to the suburbs. And for good reason: You can find a renovated three- or four-bedroom house for a sensible price (less than $500,000). A big enticement, says Coldwell Banker broker Anne DuBray, is the commute to the Loop and anywhere else: I-290, I-294, I-88, and the Metra all run through town. Stay inside city limits and you’ll find an enterprising art museum, anchored by a Mies van der Rohe house (one of only three in the United States), and multiple taprooms (Beerhead, Red Arrow) pouring city-brewed beers.

$400,000 | 421 E. School St. | 2 bedrooms | 1,200 sq. ft.

Southwest SuburbsNaperville

If a small-town feel creeps you out, this is the suburb for you: It has a downtown worthy of a little city (population 148,000), with the kinds of local businesses, such as Solemn Oath Brewery and Sparrow Coffee, beloved by urbanites. In the historic district, you won’t find cookie-cutter subdivisions, and the homes have plenty of character, like an authentic wood-burning stove in a renovated 1,200-square-foot two-bedroom (listed for $400,000) and a built-in wooden hutch in a 3,000-square-foot, four-bedroom Victorian ($650,000), both from the early 20th century.

The Expanders

Your family is growing, and you need a bigger house.

$2,075,000 | 44 Indian Hill Rd. | 5 bedrooms | 5,200 sq. ft.


$1,399,000 | 922 Cherry St. | 5 bedrooms | 5,000 sq. ft.


$1,050,000 | 1170 Oak St. | 4 bedrooms | 3,000 sq. ft.
Photo: VHT studios

North ShoreWinnetka

When you think of this village, you visualize mile-chewing mansions on the lake. But lately, buyers are looking closer to downtown: “People with families want to walk to the train and schools,” says Jena Radnay, a broker for @Properties. If you can afford it, she recommends looking on the “tree streets” (see: Cherry, Oak, Ash), where you’ll find both older, bigger houses (a four-bedroom 3,000-square-footer built in the ’30s is listed for $1.05 million) and newer, even bigger houses (two five-bedroom 5,000-plus-square-footers built in the early 2000s are going for $1.4 million, like the middle image shown above).

$475,000 | 1020 S. Seminary Ave. | 4 bedrooms | 1,855 sq. ft.

Northern SuburbsPark Ridge

In Hillary Clinton’s hometown you can find plenty of space for a half mil or less. On the market in early May: two four-bedroom Colonials for $420,000 and $475,000, a 2,000-plus-square-foot Georgian for $500,000, and even a five-bedroom, 3,000-square-foot midcentury ranch for $440,000. You’d be hard pressed to come across architectural equivalents of the same quality, size, and price in neighboring suburbs like Lincolnwood and Niles. “There are a lot of older homes with a lot of charm and character,” says Compass broker Amy Duong Kim. There’s also its proximity to O’Hare (a 10-minute drive) and a downtown with a variety of businesses, from chain stores (Trader Joe’s) to historic local landmarks (Pickwick Theatre, an art deco movie house).

$1,699,000 | 4217 Rose Ave. | 6 bedrooms | 5,247 sq. ft.

Western SuburbsWestern Springs

Living large (like in the lavish six-bedroom pictured above) doesn’t come cheap. But at the Timber Trails development, it can come Instagram ready and in at under $1 million: townhomes (2,100 to 2,700 square feet) are priced from $600,000 to $770,000, and single-family houses (3,600 to 4,300 square feet) for right around $750,000. More than 54,000 Instagrammers follow its account to see wood-beamed ceilings, shiplapped walls, and subway-tiled bathrooms. The target buyers? Says Coldwell Banker’s Dawn McKenna, a listing agent: those who “want to come out to the suburbs, want new construction, and want it to look like it came out of a magazine.” We won’t judge you.

$395,000 | 2321 N. Kostner Ave. | 6 bedrooms | 2,600 sq. ft.

Northwest SideHermosa

“People who want to be in Logan Square are making the leap into Hermosa instead and loving it,” says @Properties’ Luke Blahnik. The biggest reason? Price. Yes, Logan Square has plenty of two-flats, but as that neighborhood has heated up, the cost has too. That has buyers turning to neighboring Hermosa instead, where half the properties are buildings with two, three, or four units. In early May, four two-flats were in closing at relatively bargain prices: $245,000, $260,000, $395,000, and $400,000. Hermosa isn’t as lively as Logan Square yet, but destination-worthy food options (such as the Asian sandwich shop Hermosa) could start to draw younger Chicagoans farther west.

$309,200 | 3346 W. Rice St. | 5 bedrooms | 2,256 sq. ft.

West SideHumboldt Park

The most persuasive argument for this huge neighborhood (approximately 3.6 square miles) is its eponymous park: roughly 200 acres boasting baseball diamonds, playgrounds, and even an inland beach and a now-alligator-free lagoon. Get into the rapidly developing neighborhood while you can, because home values are quickly rising. In 2014, half of detached houses, mainly three- to five-bedroom brick workers’ cottages, went for under $86,000; by last year, the median sale price was up to $250,000. If you want a newly gutted and rehabbed version, they abound, but they’ll cost you $200,000 to $300,000 more, especially as you venture east.

$389,000 | 5023 N. Monitor Ave. | 4 bedrooms | 3,720 sq. ft.


$440,000 | 4827 W. Byron St. | 4 bedrooms | 3,075 sq. ft.

Northwest SideJefferson Park & Portage Park

Buyers looking for more space routinely ask Luke Blahnik of @Properties about these next-door neighborhoods, both with a median house sale price around $330,000. They have “larger homes on larger-than-average lots” and “a good supply of newly rehabbed inventory.” (In Jefferson Park, nearly a dozen updated single-family brick homes exceeding 2,000 square feet have sold in the $300,000s since the start of the year.) Another plus: The Blue Line runs through this area, though the ride downtown takes about 25 minutes. “People will trade off a few more stops on the CTA for a bigger house,” says Blahnik.

The New Parents

With a baby on the way, you are looking for a bigger condo or a starter house.

$350,000 | 929 Sherwood Rd. | 4 bedrooms | 1,971 sq. ft.

Western SuburbsLa Grange Park

La Grange is well known for its enchanting downtown, but you pay a premium to live there. Our suggestion? Take a five-minute drive north to this similarly named adjacent community — which is also five minutes from Brookfield Zoo and was recently rated the eighth-safest city in Illinois by SafeWise — where the median sale price drops from $558,000 to $350,000. Broker Tracy Anderson of Compass calls La Grange Park a “hidden gem,” adding that the lower prices are largely a function of its longer distance from the Metra (around 10 to 15 minutes by car from the stations in La Grange) and the high schools (Lyons Township High School, ranked 13th in Cook County by this magazine, is a 10-to-15-minute drive).

$330,000 (recently delisted) | 1653 W. 104th Pl. | 4 bedrooms | 2,048 sq. ft.

Far South SideBeverly

In this self-described “village in the city,” Italianate, Gothic, Queen Anne, and Prairie School designs — and even one Irish castle — occupy big lots on tree-lined streets. These properties aren’t just for the upper echelon: In early May, two vintage four- and five-bedroom houses with original details, like leaded glass windows and intricately carved wood columns, were on the market for $290,000. The lack of a lakefront and a longer commute to the Loop — there’s no L stop here, and on the Metra it takes 25 to 30 minutes to get to LaSalle Street Station — help keep prices lower here.

$425,000 | 2447 Birchwood Ln. | 3 bedrooms | 1,557 sq. ft.

North ShoreWilmette

Most people don’t think of starter homes when they think of Wilmette. The median sale price in this tony suburb is $740,000, and Sheridan Road mansions easily run into the seven digits. But you don’t have to be a millionaire to live here. If you know where to look, you’ll find deals on three- and four-bedroom homes. Head west of Green Bay Road for houses in the $300,000 to $500,000 range, such as an 1,850-square-foot brick four-bedroom currently listed for $449,000. Yes, you won’t be living on the poshest side of the Metra tracks, but your kid will still be enrolled in the same high-performing school district.

$255,900 | 2639 W. Gunnison St. | 2 bedrooms | 1,250 sq. ft.

North SideLincoln Square

It feels like a small town in a big city, filled with family-friendly gems, such as Timeless Toys and an Old Town School of Folk Music campus, and not far from Winnemac Park, with its playground and nature trail. Among the $700,000-plus Victorians and bungalows, you’ll find two-bedroom condos over 1,000 square feet priced from $250,000 to $300,000, though you’ll have to drop at least $400,000 if you want three bedrooms. (If those costs seem high, keep in mind that they’re a bargain compared with North Center, just two Brown Line stops away, where the median sale price of condos and townhomes is $448,000.)

The Downsizers

You’re an empty nester looking for something more manageable.

$650,000 | 1101 W. Lake St. | 2 bedrooms | 1,400 sq. ft.

Near West SideWest Loop

If you’re around Randolph and Halsted on a weekend night, you’ll see lots of people in their 20s and 30s, which is exactly why this has become a destination … for upscale downsizers in their 50s and 60s. Come again? “They want to be where the activity is, they want to not be isolated,” says North Clybourn Group’s Staci Slattery. There’s no shortage of activity here, of course: It’s home to tons of the city’s most celebrated restaurants and cocktail bars, and just a 30-minute walk east are the Art Institute, Harold Washington Library Center, and Symphony Center. But such an ideal location will cost you — two-bedrooms in condo buildings close to the action that have gyms and private patios go for $450,000 to $650,000.

$205,000 | 1550 N. Lake Shore Dr. | 1 bedroom | 800 sq. ft.
Photo: Ryan Ocasio Photography

Near North SideGold Coast

The neighborhood’s benefits are obvious: Oak Street shops, high-end restaurants, the Mag Mile, and the lake. But don’t get spooked by its reputation for being pricey. In fact, the median sale price for condos and townhouses on the Near North Side dropped 3 percent in 2019, to $398,000. It’s not all seven-figure penthouses with water views. There are also one-bedroom units without luxe finishes in both high-rise and smaller buildings that run $180,000 to $210,000. You might even luck into one on the lakefront: An 800-square-footer in a doorman building on Lake Shore Drive (shown above) was available in May for $205,000.

$200,000 (sold) | 5555 S. Everett Ave., Apt. C14 | 2 bedrooms | 1,800 sq. ft.

South SideHyde Park

Retirees tend to put a premium on having lake and park access, nearby museums, and good transit options. You can get that at a relatively affordable price point in this vibrant community, where increased development by the University of Chicago has led to a burst of new shops and restaurants during the past decade, especially right around 53rd Street and Harper Avenue. An older but move-in-ready 1,700-square-foot, two-bedroom unit across the street from the Museum of Science and Industry is priced at $165,000, and in the same building, an 1,800-square-foot two-bedroom (shown above), renovated with modern finishes, just sold for $200,000.

$789,900 | 519 Hannah Ln. | 3 bedrooms | 2,700 sq. ft.

Western SuburbsHinsdale

The standard empty nester formula goes like this: Swap your big house in the burbs for a small condo in the city. But city life is not for everyone, nor is a tiny space. For close to what you’d pay for a Streeterville two-bedroom apartment, you can get a spacious townhouse in Hinsdale, one of the Chicago area’s wealthiest communities outside the North Shore. At the year-old Hinsdale Meadows, for example, duplex villas (30, including the one shown above, of the 42 are still available, starting at $749,900) mean less maintenance on your part. “There’s no exterior work for you to do,” says Tracy Anderson of Compass, a listing agent for the development. “Somebody else is going to manage the landscaping, the snow removal, and blacktopping your driveways every other year.”

The Fixer-Uppers

You don’t mind getting your hands dirty, whether you’re looking to flip or stay put.

$232,000 | 3217 W. Walnut St. | 6 bedrooms | 1,970 sq. ft.

West SideEast Garfield Park

In the neighborhood best known for the Garfield Park Conservatory, you can find plenty of low-priced homes in need of repair, like a two-flat that’s on the market for $232,000 and a small four-bedroom house requiring a gut rehab that’s listed at $85,000. If you’re patient, you’ll likely get a big return on your investment. Humboldt Park to the north and the West Loop to the east have been saturated with new construction, and developers have started to turn their attention here, drawn by the large parcels of land where they can build multiple homes in a row, according to @Properties’ Luke Blahnik. The high crime rate might give buyers a reason to pause, but it has shown signs of improving. RentHop ranks East Garfield Park the fifth most dangerous neighborhood in Chicago. That’s three slots better than a year ago.

$325,000 | 4255 W. Devon Ave. | 3 bedrooms | 1,104 sq. ft.

Far Northwest SideSauganash

If you’re OK with putting in some sweat equity but aren’t up for taking a house down to the studs, Luke Blahnik of @Properties suggests verdant Sauganash, which is bordered by North Park Village Nature Center, LaBagh Woods, and Forest Glen Woods. Here you’ll find a healthy selection of midcentury modern homes in need of some love — mostly cosmetic renovations, like new lighting and appliances — including two 1,100-square-foot brick three-bedrooms built in 1956 that are on the market for $325,000 (shown above) and $330,000. “The beauty of midcentury homes is that they were built when building codes had been updated, in line with current construction practices,” Blahnik says. That means when you do a renovation of a kitchen or bathroom, you won’t have to pay big bucks to replace the plumbing and electrical wiring, like you might with older homes.

$329,000 | 3300 S. Parnell Ave. | 6 bedrooms | 2,000 sq. ft.

South SideBridgeport

Now’s the time to get into this blue-collar neighborhood. You won’t be the first; flippers have increasingly been jumping in to renovate an assortment of older workers’ cottages and two-flats (the one pictured above could use new kitchens and bathrooms). That’s one reason the median house sale price has jumped $120,000 since 2014, to just shy of $500,000. But there are still deals to be found for single-family homes that need considerable work — as low as $215,000 for three-bedrooms. And if flipping isn’t your jam, there are more and more reasons to settle in here, including the $23 million revival of the long-vacant 91-year-old Ramova Theatre on Halsted, which is being turned into a concert venue, restaurant, and brewery.

$210,000 | 5815 W. Roosevelt Rd. | 6 bedrooms | 2,750 sq. ft.

Western SuburbsCicero

Want to make some money renovating apartments to rent out? Don’t sleep on Saul Goodman’s hometown. “It’s a good area to invest in,” says Ryan T. Smith, a broker-partner with Re/Max Properties. “There is a large stock of multiunit dwellings, tenants are not hard to locate, and rents are stable.” Two- and three-flats that need work are regularly priced below $200,000. Two 3,125-square-foot two-flats are listed for $104,500 and $134,000, though you might end up spending twice that with the overhaul — or if you want a three-flat with an old tire shop on the lot (like the property shown above). Consider it a smart investment: The median sale price for detached housing has nearly doubled here in the past five years, to $195,000.

The Greens

You’re willing to pay a little more to be eco-friendly.

$730,000 | 147 N. Euclid Ave. | 3 bedrooms | 1,840 sq. ft.
Photo: Redfin

Western SuburbsOak Park

In 2015, Oak Park was recognized by the Morton Arboretum as the first “municipal arboretum” in the state and the fourth in the nation. To qualify, the burb had to have more than 100 species of trees, at least one dedicated employee, and policies in place governing tree care. This year, the village has added two public charging stations for electric vehicles, giving it a total of 18. And in the past four years, a profusion of upscale condos and apartment rentals with green features has sprouted up downtown. But they’re expensive: An 1,840-square-foot, three-bedroom corner apartment (shown above) in the 28-unit District House, a building with green roof terraces and solar shades, is on the market for $730,000.

$649,000 | 866 N. Paulina St. | 3 bedrooms | 1,900 sq. ft.

Near Northwest SideEast Ukrainian Village

Going green doesn’t just mean installing solar panels or buying a house built with only locally sourced materials. It can also mean getting rid of your biggest pollutant: your car. East Ukrainian Village is both the most walkable and the most bikeable neighborhood in Chicago, according to Redfin, based on criteria like distance to key amenities and number of bike lanes. That means residents can make regular trips by foot or two wheels to get all the pierogi and Hoosier Mama pies the neighborhood has to offer. But you will pay for that luxury. Detached houses run around $600,000, on average. If you stick to condos, you can get 1,300 square feet and two bedrooms for around $400,000 or, if don’t mind a longer walk (closer to Western Avenue) and less space, an 850-square-foot two-bedroom for $240,000.

$491,200 (sold) | 6454 S. Dorchester Ave. (model shown) | 4 bedrooms | 2,100 sq. ft.
Photo: Marni Beals Photography

South SideWoodlawn

The eventual home of the Obama Presidential Center is where you can already find the recently opened Green Living Room, an eco-focused coffee shop, workspace, and community gathering spot and headquarters for Blacks in Green, an organization that supports environmental sustainability in African American communities. This neighborhood is also where Greenline Homes, a local developer specializing in eco-friendly properties on the South Side, has built 75 of its 83 single-family homes (a model is shown above), two-flats, townhouse units, and condo buildings. None are for sale at the moment, but seven more single-family homes are in the permit stage, and all will bear the highest rating from the U.S. Green Building Council. While prices of these new Greenline houses will be steep — $450,000 to $500,000 — detached homes in this neighborhood are appreciating fast, from a median sale price of $44,000 in 2014 to $140,000 last year.

$1,180,000 | 630 Central St. | 5 bedrooms | 3,700 sq. ft.

North ShoreEvanston

In the market for a home with features such as solar panels, spray-foam insulation, high-efficiency HVAC, and systems that purify and recycle wastewater? Then Evanston is the place to be, says Mark Weitekamper, a green-focused contractor and a broker with Haderlein and Company Realtors. (Ask your agent to use the “green features” tab in a multiple listing service search.) Two years ago, the suburb adopted a plan that calls for 100 percent renewable electricity by 2030 and carbon neutrality and zero waste by 2050. Walgreens also put its first-ever net-zero energy store here almost seven years ago. Access to both the Purple Line and the Metra Union Pacific North line can help residents reduce their carbon footprints even more. The median sale price of houses in Evanston is $510,000, but the bigger properties with the most progressive green elements (like the one shown above) can run more than $1 million.

What Your Home is Worth

The latest price data for 74 neighborhoods and 227 suburbs

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2019 housing data

NOTES: Price data is given only for places with at least 20 house sales or 20 condo sales in 2019. In the suburbs tables, towns that straddle two or more counties are listed in the county where they have the greatest population.
SOURCE: Midwest Real Estate Data, an aggregator and distributor of data for Chicago and its collar counties; MRED does not guarantee the accuracy of the data, which may not reflect all real estate activity in the market.