Photograph: Courtesy of

$850,000: Recent list price for 2-bedroom condo at 360 East Randolph; a 1-bedroom here lists for $229,000

Looking for a small condo so you can have a place downtown? Now is a good time to get in the market—but the best deals are available on properties just outside the hottest part of downtown.

The whole point of owning a small second home in the city is to be right where the action is. Unfortunately, prices of one- and two-bedroom condos in the desirable neighborhoods—River North, Streeterville, the area around Michigan Avenue—haven’t fallen nearly as much as the metro area’s 38 percent average. We group them as part of the Near North Side, where condos are down a mere 2.9 percent since the peak.

But there are still some neighborhoods that make good sense for this kind of investment. Here are three good options—they’re still convenient to restaurants and theatres, but each offers a greater chance of scoring a (relative) bargain.

Typical price for a one-bedroom condo (based on analysis of listings at presstime): $270,000

This historic neighborhood—roughly bordered by Armitage Avenue and LaSalle, Division, and Larrabee Streets—offers Old World appeal that glitzier parts of downtown often lack. (Old Town is considered part of the larger Near North Side.)

Pat and Bruce Leshinski, who have a house in southwestern Michigan, love that their two-bedroom Wells Street pied-à-terre (purchased in 2008 for about $700,000) is surrounded by shops and cafés—and that it’s close to Lake Michigan beaches and the southern end of Lincoln Park. For the best prices, check out the area south of North Avenue, which once bumped up against the now-demolished housing project Cabrini-Green.


$160,000: List price for 1-bedroom condo at 400 East Randolph

Photograph: Matt Kawa/

$160,000: List price for 1-bedroom condo at 400 East Randolph

Typical price for a one-bedroom condo: $200,000

As recently as 15 years ago, the string of condo and apartment towers on Randolph Street, between Michigan Avenue and Lake Shore Drive, felt a bit remote. Then along came Millennium Park in 2004 and the thriving Lakeshore East development—which began to take shape at about the same time—and suddenly Chicago had a sizzling new downtown neighborhood. (It’s considered part of the Loop, where median condo prices are 9 percent higher now than in 2006.)

Prices in Lakeshore East typically exceed $600 a square foot, but in older Randolph Street buildings, such as the Buckingham (360 East Randolph), 400 East Randolph, and Harbor Point (450 East Randolph), you will find condos going for less than $500 a square foot—and often below $400.


$199,000: List price for 1-bedroom condo in Printers Row

Photograph: Ratko Radojcic

$199,000: List price for 1-bedroom condo in Printers Row

Typical price for a one-bedroom condo: $210,000

In this section of downtown, the handsome old loft buildings, many artfully trimmed with terra cotta, offer a charming alternative to sterile new South Loop high-rises.

Located south of Congress Parkway and west of State Street, Printers Row was a virtual island until the beginning of the 21st century, when the South Loop boom surrounded it with new houses and condos, restaurants, and big-box shops along Roosevelt Road. According to Zillow, the average condo price here is about 10 percent lower than elsewhere in the South Loop.

$41 billion: That’s how much foreign buyers spent on pieds-à-terre and other U.S. residential real estate in the year ending March 2012, says the National Association of Realtors. Those investments helped fuel the Sun Belt housing revival, with Florida getting the biggest chunk: 26 percent. Chicago got less than 2 percent.

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