Not even the leaden skies and single-digit frigidity of a recent January afternoon could hide the fact that Jackson Park feels like an urban resort district, tailor-made for hot, sunny days.
"In the summertime, it's nice to just walk around along the beach," said Ware. "They have a triathlon for kids — a bike-run-swim — at 63rd and the lake. There are a lot of runs and biking events in the Jackson Park area. It gets you outdoors and relaxing."
Jackson Park residents can also walk, jog or in-line skate through the namesake park, hit the links at the 18-hole Jackson Park Golf Course or nine-hole South Shore Golf Course and pilot their boats from the harbor adjacent to La Rabida Children's Hospital, Gibson and Ware said.
At the very north end of the park called Jackson Park, which is directly north of the neighborhood bearing the same name, stands the famed Museum of Science and Industry. And inside the park is the Osaka Japanese Garden, located on Wooded Island just south of the museum.
Another distinctive feature of the community, which is bordered by 67th and 71st Streets, the lakefront and Stony Island Avenue, is its rich variety of vintage housing. Whether stately 2 1/2-story brick single-family homes in Jackson Park Highlands, or the elegant red-brick apartment buildings for which Jackson Park is known, the residences are historic, solid and voluminous, said Ald. Leslie Hairston, whose 5th Ward covers Jackson Park.
"The housing stock of this community was built for a professional class of people. Many owned businesses on what was then very ritzy 71st Street, or were affiliated with the faculty or administration of the University of Chicago," said Hairston.
Some of the 100-year-old-plus apartment buildings feature original walnut woodwork, wainscoting, elaborate lobbies and extra-large windows, she noted.
"Everything was custom, particularly in buildings on Crandon and Oglesby [Avenues]," Hairston said, adding some units sprawl to an enormous 3,500 square feet and larger.
The apartment stock is lauded by working folks like Ron Ames, barber at B Selfish Salon & Barber Shop, 2300 E. 71st St., who said he likes how well-maintained the buildings are. "They keep the property up real nice," he said.
Nestled within Jackson Park is Jackson Park Highlands. The uninitiated could be forgiven for calling it "part of" Jackson Park. Jackson Park Highlands is actually a separate community, and one of the most beautiful in Chicago. Extending from Euclid to Cregier Avenues, and 67th to 71st Streets, the Highlands is a historic district of architectural gems built from 1905 to 1925.
Many of the houses in the Highlands are so large and distinctive they defy easy categorization. They're not Georgians, but most don't quite qualify as mansions. Many are two- and 2 1/2-story homes featuring dormers and porches, and set back from the streets to create handsome front lawns, Ware said.
Residents of Jackson Park Highlands are fastidious about maintaining their enclave, and also are active in the larger South Shore community, said Robert Van Puyenbroeck, a 14-year Highlands resident and former president of the Jackson Park Highlands Homeowners Association. Many donate time to help clean up and maintain the park, or volunteer at the museum, he said.
The exclusivity of Jackson Park Highlands is reflected in its home prices, which go from $400,000 to $900,000, Ware said. Elsewhere in the area, single-family homes are priced from $150,000 to $350,000, and many apartment rentals can be fetched for $650 to $750 a month on one-bedrooms, she added.
Paul Gibson grew up in Jeffery Manor. But as a teenager he often tagged along with a friend when the friend visited his uncle. His first look at the uncle's home in the Jackson Park Highlands neighborhood blew young Gibson away.
"I said, 'Wow! I didn't know these types of homes existed within the city limits. When I grow up, I want to live here,' " Gibson recalled with a chuckle.
It took him more than two decades, but over the Fourth of July weekend seven years ago, Gibson moved with his wife to their newly-purchased home on 68th Street in the same Jackson Park Highlands enclave he so admired.
"My wife and I love it," he said of their neighborhood.
Gibson, a Realtor with the Hyde Park office of Coldwell Banker Residential Brokerage, and a certified residential real estate appraiser, isn't the only one who set his sights on "the Highlands," or the separate and larger Jackson Park community that extends east and west of it, over the years.
"In summertime, when we walk along the lake in the morning, it looks just like Catalina," Gibson said. "The boats on the harbor, the golf course behind you, it's nice. You have joggers, walkers and bikers on the lakefront, and there are the local fishermen there too."
The best bargains in the area are on condos. "The condo market has been hit hard in Jackson Park; they have really taken it in the neck," Gibson said, noting most sales in the past six to 12 months have been bank foreclosures. Financing is difficult but if you have cash, there are condos for $20,000, he said.
The key to remember about all domiciles in this community is they are a scant 10 minutes from the Loop, Ware said. CTA buses and Metra Electric South Shore Line trains whisk residents quickly to Chicago's busiest commercial districts. And, she added, "On a good day, you can ride your bike downtown."
What the community most needs is more restaurants and retail venues. Though Hairston has lured a number of national and regional retailers to the Jackson Park area in her 11 years as alderman, she would like to see more commerce. "I'm speaking with restaurateurs to bring some restaurants to the lakefront," she said. "And I would love to see a Target on Stony Island."
That would help make the neighborhood some see as a well-guarded secret an even nicer place to be. As Ware observed: "It's like a hidden gem."