Highland Park Real Estate and Entertainment Guide
Highland Park Real Estate and History

Frank Lloyd Wright's Willits House
Highland Park is one of the affluent Northern Suburbs of Chicago that actually borders Lake Michigan. Now a town of around 33,000, it originally consisted of two settlements, St. John and Port Clinton. Like many North Shore Chicago suburbs, it has a great school system, expansive green spaces and parks, and it pays special attention to the arts with fine art and film festivals in the summer.
If Highland Park real estate looks familiar to you, it might be because it has been featured in many movies, especially those of John Hughes. Home Alone, Ferris Bueller's Day Off, Weird Science and Sixteen Candles all filmed scenes in the town, along with a host of other movies. Nowadays, Highland Park real estate is characterized by a variety of styles, from Frank Lloyd Wright homes to classic Victorian properties. Highland Park has many notable residents, both past and present. Actor and director Orson Welles called Highland Park home during a part of his life, as did musician Billy Corgan. Michael Jordan made his home in Highland Park during his time with the Chicago Bulls and continues to live there, along with Chicago Bulls coach Vinny Del Negro.
It is a popular suburb for many who work downtown since the commute is made easy by accessibility to six Metra stops in town. However, Highland Park is also the home to corporate headquarters of many companies, like the Solo Cup Company, providing local jobs.
Ultimately, Highland Park has the gorgeous views and the excellent recreation provided by five miles of Lake Michigan shoreline, and it's located only 26 miles north of downtown Chicago, making it a great place to make a home.
Events and Activities in Highland Park

Ravinia – Highland Park
- Frank Lloyd Wright's Willits House – Lake Forest hosts several Wright homes, and many homes designed by other notable architects, but the most famous is the Willits House built in 1902. It is considered to be the first house designed in the prairie style.
- Ravinia – The main attraction of Highland Park - and the one that brings people from all over the state in the summer months - is Ravinia Park. The park has various indoor and outdoor venues for the performing arts, and it is home to the oldest outdoor music festival in the country. Each summer the park not only plays home to the Chicago Symphony Orchestra, but also hosts contemporary music acts throughout the season. The Ravinia area, on the south of Highland Park and annexed by the city in 1899, was previously an artists' colony and still brings that spirit and character to the city.
- The Park District of Highland Park – Covering 600 acres of parklands, including three parks located on the shores of Lake Michigan, the Park District is one of the best amenities Highland Park has to offer. Owners of Highland Park real estate enjoy an indoor ice rink facility, tennis courts, racquet ball courts, a yacht club, 18-hole golf course, numerous bike trails and the 96-acre Heller Nature Preserve.
- Port Clinton Art Festival – Late August brings the two-day Port Clinton Art Festival to Highland Park, letting residents view art, taste food, and enjoy the end of summer in the outdoors. Now in its 26th season, it is heralded as one of the best art festivals in the nation.
Restaurants Near Lakeview Real Estate

Walker Bros. Original Pancake House
- Breakfast – For breakfast in Highland Park, you can try Once Upon A Bagel, a bakery and deli offering every kind of bagel topped with anything you can think of. For a more classic breakfast, check out Walker Bros. Original Pancake House, a North Shore staple for baked pancakes. Country Kitchen provides a breakfast menu that feels like Mom made it — comforting and filling.
- Sweets – Highland Park is rich with candy shops and confectioneries. Goodies, Etc. provides the best, hand-packaged gift baskets of chocolate and candy. Carol's Cookies, delicious half-pound monster cookies, are now available all over the country in upscale gift shops but the headquarters is right at home in Highland Park.
- Mexican – You have your choice of a few Mexican food joints in Highland Park or neighboring Highwood. Try Los Mogotes De Michoacan for an authentic and extremely affordable Mexican meal. Just be prepared for the fact that it is cash only and is nestled into a strip mall. You might also try Tamales, for its house specialty or another dish. You'll find classic Mexican dishes and some twists on the originals, like pumpkin tamales and duck tacos.
- Comfort Food – Simple soul food can be found in town, too. Try Bluegrass for Cajun-style dishes from baked beans to jambalaya, plus all-you-can-eat ribs on Tuesday nights. For Chicago-style red hots and other greasy grub, Michael's is where you should head. The hot dog shop serves up high-quality fast food and is a great casual spot for families. For more upscale American comfort fare, try City Park Grill for lunch or dinner. Owned and operated by North Shore locals, it's sure to please.
- Pizza – Of course in Chicago, pizza merits its own category. In Highland Park, you can have a pie delivered from Piero's Pizza or pick up a pre-made pizza to cook at home at your leisure. Viccino's Pizza Company also serves up pizza but in a gourmet style, and many argue that it's the best of the North Shore.
- Italian – In the neighborhood, you can try one of the famous Rosebud restaurants, a Chicago chain of old world Italian eateries. Rosebud of Highland Park offers an outdoor café, wines from around the world, and daily market specials. Del Rio is an unpretentious eatery, with a homey ambiance and comforting Italian dishes.
Bars and Nightlife in Highland Park

Gabe's Backstage Lounge
- Gabe's Backstage Lounge – A favorite spot of young locals, Gabe's offers lounge appeal and live music. With drink specials every night and a beer garden during warm weather, it's a great place to relax and enjoy the company of friends.
- Teddy O'Brian's – Teddy O's, as it is known to locals, is another hot spot for young folks from Highland Park and its surrounding suburbs to meet and mingle. Friendly faces and friendly bartenders will keep you coming back!
- Bridie McKenna's Irish Pub – A relatively new spot in the area, Bridie McKenna's provides traditional Irish food and spirits that give you a truly authentic pub experience. Opened by an Irish–born Chicagoan as a tribute to his mother, Bridie's offers "the warmest welcome on the North Shore" to its patrons.


