In Roscoe Village, older buildings (like the one above, near Roscoe Street and Damen Avenue) now house funky boutiques.

Average house price: $869,354
Transportation * * * (out of 4) Pick up the Brown Line at Lincoln Avenue, a few blocks east of the neighborhood; the Kennedy Expressway is about two miles west.
Schools * * * Test scores at Audubon Elementary surpass the city average by 15 points.
Shopping * * * * Funky shops and restaurants line Roscoe Street, selling everything from healthy meals to hip baby clothes.
Plus: Retro on Roscoe, the annual two-day fest that shows off the neighborhood, starts August 7th.

On their usual circuit through the neighborhood, Kristen and Victor Ramirez and their two small children have a lot to do. They need to get their feet wet in the swimming pool at Hamlin Park; stop to see the penguin statue outside Suckers Candy; drop in at Glam to Go and a couple of other Roscoe Street boutiques; and finish with some sugar cookies from the old-timey Rudy’s Bakery. The family’s list of stops around their Roscoe Village neighborhood is testament to how a onetime tavern strip whose trolley line led into the legendary Riverview amusement park has been transformed into a cheery, magnetic neighborhood for young urban families.

Roscoe Village is not a new hot spot by any stretch; loft-hunters first found it in the 1980s. Nonetheless, it offers opportunities for surprising discoveries. “I still feel like it’s our own hidden gem,” says Kristen Ramirez. “Even people who come here for Retro on Roscoe don’t seem to know that there are all these other little treasures here.”

Some homes in the neighborhood are pricey—in the recent building boom, many old residences got million-dollar replacements—but there are also apartments and, since the downturn, some opportunities for bargain-shoppers to pick up distressed properties. As for the Ramirez family, since their older child landed a coveted spot at the Audubon school, where he is in the pre-K program, their intention is to stick around and keep doing the circuit.

Photograph: Tim Klein