Back in 1999, Ramesh and Nieva Mehta gave their friends a shock. They announced that they were selling their house in north suburban Arlington Heights, where they had lived for 26 years, and moving to a condo in River North. Ramesh was tired of commuting to his job downtown (as a program manager in IBM’s real estate services unit), the couple explained, and their two kids were grown and gone. What’s more, says Ramesh, “we realized we could use our time for something better than clearing snow”—such as strolling to theaters, museums, and restaurants.

Sixteen years later, such announcements are far from shocking. To many in the huge baby-boom generation (who are now ages 50 to 68), a big house is looking less like the American dream and more like an albatross. In the Chicago area, downsizing from a house in the burbs to a city condo used to be mostly a Winnetka–to–Gold Coast kind of thing, according to Gail Lissner, vice president at the real estate consulting firm Appraisal Research Counselors. That has changed considerably, she says: “The migration is much broader in both source and destination.”

Among the recent refugees are Tracey and John Kreiling, empty nesters in their 50s. Last summer they moved from a Victorian in west suburban Glen Ellyn to a shiny glass condo in the South Loop. “We had a gathering of 40 or 50 people the other night,” Tracey says, “and I was struck by how many of our friends said they were a year or two away from a move to the city.”

Another demographic shift is underway too: In 2015, members of the huge millennial generation turn 25 to 35 (or 18 to 34, depending on whom you ask). This is the age range at which people typically buy a starter home, often a condo.

Such demand is reflected in Chicago’s 2014 data tables, supplied by Midwest Real Estate Data. For example, last year in Lincoln Park—the nabe with the most even split between houses and condos—the average condo sold nearly twice as quickly as the average house. As for price? The median condo in Lincoln Park sold for 14 percent more last year than it did in 2006, at the height of the housing bubble. The median house price there rose only 9 percent.

• 16 Sweet Buildings:
• Post-2000 Condos
• Mid-Century Condos
• Prewar Condos & Co-Ops
• Suburban Condos

This pattern does not hold true in all neighborhoods, mind you. House prices have risen faster than condo prices in Lake View, the Near North Side, and North Center, for example. But in Lincoln Square, Logan Square, and the Near West Side, condos came out on top. And check out the Loop: Median condo prices there soared 21 percent in the past eight years. No Chicago neighborhood or suburb had a higher increase, regardless of housing type.

Thinking about entering condoland yourself? Armed with the wisdom of independent real estate experts, agents, owners, and community leaders, I identified 16 excellent condo and co-op buildings (more on co-ops later) at a variety of price levels. They all have strong prospects for appreciation, based on key advantages such as location (proximity to the lake, transportation, shops, restaurants), aesthetics (whether a glass-and-steel tower or stately stone edifice), and amenities (doormen, garage parking, pools). Let’s get started!

Post-2000 Condos

All those shiny towers sprouting up right as the real estate boom was peaking! All that unsold inventory languishing on the market for years afterward! Buyers have sopped up much of the excess by now. But given that 82 condo buildings containing nearly 16,000 units have opened in or near downtown in the past 10 years, there’s still plenty on the market.

The biggest pros to one of these buildings—besides the fact that new stuff requires less maintenance—tend to be expansive windows, glossy finishes, and amenities galore. The biggest con (if you’re a quiet-seeking buyer of a certain age): Rooftop pools, party rooms, yoga studios, and the like are big draws for millennials, too.

The six standout condo buildings that follow—listed from lowest to highest median sale price—all offer 24-hour doormen, fitness centers, and garage parking.

If you crave natural light and a good value

Skybridge
737 W. Washington Blvd., West Loop
Built: 2003
Style: Modern
Units: 237 (14 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $485,000

The “bridge” in Skybridge? A glass hallway that spans a gap slicing the building in two from the 10th floor to the roof, giving each floor eight corner exposures. Because this 39-story concrete structure is the tallest west of I-94, you get vistas that may not include Lake Michigan but are stupendous nevertheless: the abruptness of office towers, the expansiveness of big sky. You’ll also get a rooftop garden, and, any day now, a Whole Foods right at your feet. True, the median sales price here runs $170,000 higher than the $315,000 median for this neighborhood. But for a luxury building, that’s a good deal.

If you love the burgeoning Clybourn Corridor area

SoNo
860 W. Blackhawk St., Near North Side
Built: 2009
Style: Modern
Units: 200 (16 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $518,000

Don’t confuse SoNo with its twin, SoNo East, a rental building. This tower—its blue-glass façade cantilevered and etched with balconies by famed Chicago Seven architect Laurence Booth—is one of very few new(ish) condo buildings of any size in the bustling Clybourn Corridor near the southwestern edge of Lincoln Park. Hence the relatively steep price for the nabe. While your assessment ($560 a month for a 1,415-square-foot two-bedroom unit) may seem on the high side, it covers all utilities, high-speed Internet, and basic cable in addition to standard building services.

If you want parkland and lakefront without a million-dollar price tag

The Grant
1201 S. Prairie Ave., South Loop
Built: 2010
Style: Contemporary
Units: 298 (87 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $754,000

For science nerds and outdoor lovers alike, this sleek 54-story luxury tower’s location alongside Grant Park—with the Field Museum, the Shedd Aquarium, and Lake Michigan just beyond—is hard to beat. The Grant will be particularly appealing if you’ve got a spouse and kids, given the many three-bedroom units and a spacious common playroom for children well stocked with toys and games (there are frequent organized kids’ activities too). The median sales price here may not seem like much of a deal, but similar spaces to the north can run up to twice the price.

If you’re all about convenience (and the Bean!)

The Legacy at Millennium Park
60 E. Monroe St., Loop
Built: 2009
Style: Modernist
Units: 360 (35 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $830,000

It’s yet another blue-glass tower (sigh), but the Legacy stands out anyway. At 822 feet and 73 stories, it’s the 12th-tallest residential building in the nation (see page 60), muscling above the historic street walls of Michigan and Wabash Avenues. You won’t choose this place for its price per square foot (around $570 versus the $350 Loop average), but for convenience, especially if you’re a member of the adjoining University Club: A footbridge connects the two buildings. Another plus: Owners can rent out their units without restriction, so long as each lease lasts at least one year.

If you want to live like royals (and maybe rub elbows with them too)

Lincoln Park 2550
2550 N. Lakeview Ave., Lincoln Park
Built: 2012
Style: Beaux-Arts/Second Empire
Units: 218 (39 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $1.33 million

With its Napoleon-and-Josephine vibe (if you’re into that) and its huge list of amenities (indoor pool, kids’ play area, 1.5-acre private park, etc.), this Lucien Lagrange–designed condo building is surely the most extravagant to open in Chicago since Trump Tower. Despite the lofty median sales price listed above, you can buy a home at Lincoln Park 2550 for less than you might think, so long as you don’t need much space. Two of the 12 units that remained unsold at presstime were one-bedrooms listed in the mid-$500,000s.

If you’re a captain of industry who wants to pretend you never left Winnetka

4 East Elm
Gold Coast
Projected completion date: 2016
Style: Modernist
Units: 35
Median sales price for units currently under contract: $2.90 million

Did I say Lincoln Park 2550 was luxurious? Just wait for this “boutique” condo building at 4 East Elm Street, which broke ground last September and is due to open next spring. Most apartments here will cover a full floor, and all will have keyed elevator access. So they’ll have the feel of standalone houses, says Mike Golden of @properties, who’s handling sales. But with shared amenities usually seen only in much larger buildings—sun deck, pool, spa, gym, theater, etc.—expect this place to feel more like a superexclusive country club. Chicago’s one-percenters seem to be eating it up: At presstime, more than half the units were under contract.

Mid-Century Condos

The world knows Chicago as the capital of modernist architecture, so why not live in the genuine midcentury article? While there are no guarantees that such condos will appreciate more rapidly than others nearby, it’s hard to imagine that foreign buyers—who are checking out the city in increasing numbers—wouldn’t be interested in owning a piece of, say, a Mies van der Rohe masterpiece. The best midcentury condo buildings in Chicago tend to be those that hew most closely to the minimalist ideal: clean-lined glass, steel, and concrete, with little to no adornment but tons of urban sophistication. The three listed here stand out in part because they were designed by giants of modernism and because they’re large enough to offer a diverse stock of units for sale.

If you’re a Mies devotee who doesn’t mind giving away half your furniture

Esplanade Apartments
900 and 910 N. Lake Shore Dr., Streeterville
Built: 1955
Units: 524 (24 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $378,000

Let’s get the negatives out of the way: low ceilings (eight feet), small sizes (mostly compact one- and two-bedrooms), and limited amenities (these apartments were built 60 years ago, after all). But among the city’s Mies residences, those here stand out because they showcase the master at the height of his powers and because they’re condos (which carry fewer restrictions than his co-ops at 860 and 880 North Lake Shore Drive). You can combine them, as did architect residents Margaret McCurry and Stanley Tigerman, into a spacious homage to modernism. Says Tigerman: “This is perfection to me.”

If you want to live in a self-sufficient bubble over the lake

Lake Point Tower
505 N. Lake Shore Dr., Streeterville
Built: 1968
Units: 758 (40 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $557,000

This iconic clover-shaped tower, designed by Mies apprentices George Schipporeit and John Heinrich, is “the most beautiful skyscraper in the United States,” according to historian Neil Harris’s 2004 book Chicago Apartments. It went up before the city nixed residential development east of Lake Shore Drive, ensuring permanent lake-in-your-face views from every unit. Its indoor-outdoor pool, 2.5-acre raised park, onsite garage, and food market have attracted everyone from David Axelrod to Sammy Sosa. And yet these condos tend to be cheaper than those in nearby Aqua or the Chandler, perhaps because units may need updating—or because the location feels a bit isolated to some.

If you want genuine period design plus the amenities of a new building

The Montgomery
500 W. Superior St., River North
Built: 1972
Units: 250 (20 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $608,000

Designed by Minoru Yamasaki, the architect of the original World Trade Center in New York City, this 28-story concrete monolith had a decidedly unglamorous function: headquarters for Montgomery Ward, catalog retailer to the masses. Its location hard by Cabrini-Green’s drab towers wasn’t exactly exclusive, either. But with the housing project demolished, a new cluster of residential towers along the river just to the south, and the epicenter of Chicago dining and drinking now barely half a mile east, the Montgomery—which went condo in 2005—has become one of the city’s most desirable buildings. Thank its many luxury amenities, which include a fitness center, rooftop deck and cabana, and private dog run. You need not even suffer the low ceilings common in midcentury modern construction: Each unit has 10-foot window walls. No wonder the typical apartment here goes for nearly double the median price on the Near North Side.

Prewar Condos & Co-ops

The period between World Wars I and II was a golden age for apartment building. Wonderful examples pepper the Gold Coast and East Lake Shore Drive—rock-solid structures with gracious courtyards, large and well-proportioned rooms, high ceilings, and elaborate moldings. These grandes dames still house the city’s elite. But paying seven figures to live in that part of town isn’t the only option for lovers of 1920s architecture. At right, see two considerably less expensive Chicago buildings from the era (OK, one is from the 19th century).

Note that three of the five buildings listed in this section are co-ops. Unlike with condos, in which you buy your unit outright, this form of ownership is a partnership in an entity that owns the building. In practice, the main difference is that co-ops have much more control over who gets to buy in and what you get to do with your unit (rent it out, for example). Monthly fees are usually higher, too—sometimes dramatically so.

If you’re young and single or a suburbanite looking for an affordable pied-à-terre

The Brewster
2800 N. Pine Grove Ave., Lake View
Built: 1893
Style: Romanesque Revival
Type: Condo
Units: 90 (three sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $95,000

That price isn’t a misprint. The midrise Brewster used to be a rooming house; it went condo in 1979, combining some units into one- and two-bedrooms. But many remain as studios, some a teeny-tiny 300 square feet. Scoff if you must—but they can be a good option for 20-somethings who would have a hard time affording the neighborhood otherwise. Noreen Czosnyka, a real estate agent who lives in Jefferson Park, helped her son Brian buy a studio here in 2002; she liked it so much that she bought one as a pied-à-terre two years later. “Everything you need, green space included, is within three blocks,” says Brian.

If HGTV’s Rehab Addict has given you some ideas

3750 North Lake Shore Drive
Lake View
Built: 1926
Style: Neoclassical
Type: Co-op
Units: 130 (seven sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $340,000

From some of the large apartments in this brick and limestone doorman building (with a vintage indoor pool!), you can gaze straight at the boats in Belmont Harbor. (Room size matters, notes Mary Kaye Buettgen, an agent with Baird & Warner: “A lot of downsizers still need a floor plan that can handle piles of furniture.”) So why do apartments here go for around the condo median for this nabe? Condition, for one thing: many need work. Paging Nicole Curtis!

If you’re devoted to the South Side

Powhatan Apartments
4950 S. Chicago Beach Dr., Hyde Park
Built: 1929
Style: Art deco
Type: Co-op
Units: 40 (three sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $430,000

Welcome to the grandest dame on the South Side (just across the line separating Hyde Park from Kenwood, President Obama’s nabe). It doesn’t get more deco than the Powhatan’s stunning lobby and rotunda, encrusted with colorful tile mosaics depicting Native American culture. And while some of the apartments feel a little tired, most are comfortably appointed and generously sized. As for classic amenities, how do staffed elevators, an indoor swimming pool, a rooftop deck, and a ballroom sound? The catch (you knew there’d be one, given the median unit’s sub-$500,000 price): Co-op fees hit about $3,000 a month for a large three-bedroom. Run the numbers carefully before you pounce.

If you’re a deco lover with a Hugh Hefner fixation

The Palmolive
159 E. Walton St., Gold Coast
Built: 1929
Style: Art deco
Type: Condo
Units: 102 (13 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $1.05 million

From soap company offices to Playboy headquarters to condos (a transformation that occurred 10 years ago), this Holabird & Root building right off the Magnificent Mile remains a landmark of Chicago’s North Side. Most units are two- or three-bedrooms with at least 1,500 square feet; many have elegant interior finishes; and some boast private terraces. The place is a magnet for boldface names: Residents have included actor Vince Vaughn, former Cubs manager Lou Piniella, and the CEOs of several large companies. Crave Vaughn’s triplex penthouse, which includes Hugh Hefner’s old office? It’s on the market at the reduced price of $13.90 million.

If you’re a traditionalist with social connections and buckets of cash

1500 North Lake Shore Drive
Gold Coast
Built: 1929
Style: Neoclassical
Type: Co-op
Units: 57 (five sold in the 24 months ending February 15)
Median sale price (for the 12 months ending February 15): $2.30 million

Along with Drake Tower and 209 East Lake Shore Drive, this stately stone building is one of the most exclusive in Chicago. It’s a discreet old-money kind of place where each enormous apartment is unique, uniformed staffers fetch your car, and everyone has a perfect view of Lake Michigan. Perhaps because many prominent bankers have lived here over the years (as have scions of families named McCormick and Wrigley), the co-op board screens would-be buyers rigorously. If you lack millions in assets and impeccable social and professional references, forget about buying one of the two apartments listed at presstime (for $3.50 million and $3.78 million).

Suburban Condos

While most Chicago suburbs contain a few condos, only two offer a significant number: Evanston and Wilmette, both on the tony North Shore. If you prefer to buy new (or newish), go to Evanston, which got swept up in the ’00s condo building boom at the same time Chicago did. The past decade unleashed more than 1,500 units on this 75,000-person burg. By contrast, Wilmette’s condo boom occurred 50 years ago. Here’s the standout building in each town. Both have 24-hour doormen and garage parking, plus shopping and transit close at hand—and, unfortunately, prices higher than you might expect.

If you’re so over the burbs yet want to be near North Shore friends and family

The Residences of Sherman Plaza
807 Davis St., Evanston
Built: 2006
Style: Postmodern
Units: 253 (26 sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $404,000

The area sure feels Chicago-like, with stops for Metra and the el a block from the building, gobs of stores, a multiplex theater, and a parking garage and gym connected to the building. The Residences’ size is cityish too: It contains more condos than anyplace built in Evanston in the past 10 years. You may not adore the faux-industrial aesthetics, but the high ceilings and balconies in every unit are a definite plus. And it’s tall enough that some units nab lake views.

If you’re a retiree who wants friendly neighbors your age

1420 Sheridan Road
Wilmette
Built: 1969
Style: Modernist
Units: 74 (five sold in the 12 months ending February 15)
Median sale price (for the 12 months ending February 15): $780,000

The half-dozen condo and co-op buildings nestled between Sheridan Road and Lake Michigan are all known for their neighborliness, especially among their many older residents. But the pleasingly fortress-like 1420 Sheridan—a condo building—is closest to the beach, with floor-to-ceiling windows that practically bring the lake inside, plus a heated outdoor swimming pool and a veranda with gardens. All units have at least two bedrooms, with prices ranging from $290,000 to more than $1 million (for a 3,500-square-foot three-bedroom). You get a lot for your monthly fee, including garage parking, an attentive staff, and lots of common space for activities with your new BFFs.