North Shore Outdoor Dining

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If you would like to make an appointment, call or text Scott Gettleman at 773-875-6792 or email

Highland Park
Named for its park-like setting and lofty elevation, this Lake County city boasts great restaurants, downtown areas and several beaches. Ravinia Festival hosts various types of live concerts throughout the summer months. Most of the housing market in Highland Park is made up of single-family homes, although there are townhouses and condos available as well. John Hughes directed many 1980s films in Highland Park locations. A true mix of vintage and modern, Highland Park has a feel of suburban life with hints of city living.

Places to Visit:
Rosewood Beach
Moraine Park
Ravinia Festival

Located just West of Highland Park and 25 miles from Downtown Chicago, Deerfield is home to many large corporations and has become an area of employment for thousands of educated professionals and their families. Close to transportation, this neighborhood is comprised mainly of single family homes. Constantly being developed, Deerfield incorporates downtown shopping areas and great restaurants.

Places to Visit:
Deerfield Historic Village
Brunswick Zone
Harvest Fest

With top-ranked schools, the community of Northbrook is comprised of picturesque parks, renowned restaurants and shopping centers. Northbrook is close to transportation and is the home of many large corporations, such as Walgreens and Crate & Barrel. This neighborhood has maintained greatness since the early 1900s and is continuing to grow.

Places to Visit:
Chicago Botanic Gardens
River Trail Nature Center

Located just south of Northbrook, this affluent area of the North Shore has been recognized by Business Insider as having some of the best public schools in the country. Originally centered around “The Park”, Glenview’s most coveted neighborhood, Glenview has recently built The Glen, a centralized area with top-notch shopping and restaurants. The community hosts several events for all ages throughout the Summer months.

Places to Visit:
Kohl Children’s Museum
Historic Wagner Farm

Lake Forest
Along the shore of Lake Michigan, Lake Forest has been the setting for scenes from movies such as Ordinary People, Ferris Bueller’s Day Off and Ocean’s Twelve. Single family homes in East Lake Forest have large lots and combine both vintage homes and new construction. Award-winning Lake Forest College sits near the scenic and charming downtown area.

Places to Visit:
Market Square
Popcorn Factory Store

Only 15 miles North of Chicago, Winnetka is known for its great estates and remarkable history. Comprised of mainly single-family homes, most families move to Winnetka for the distinguished schooling system and proximity to Chicago. Great restaurants and boutique shopping can be found along Green Bay Road, which is a central location of the town.

Places to Visit:
Skokie Lagoons
The House from “Home Alone”

Nationally awarded schools, access to transportation, and closeness to Lake Michigan give Wilmette the honor of being the seventh best place to raise children in the U.S., according to Business Week. As with most North Shore communities, Wilmette houses great restaurants and boutique shops. Single-family housing located throughout the city, with condo buildings lining the coast of Lake Michigan gives buyers options of lifestyle and community.

Places to Visit:
Gillson Park
Wilmette Historical Museum

Fort Sheridan
With walking paths along Lake Michigan and breath-taking ravines, Fort Sheridan is comprised of both Highland Park and Highwood. Originally an Army Base, this area is a great community for families and those looking for easy-living, Historical homes and landmarks tell a remarkable story of the past, which is evident through the scenic properties and original Army housing. The town of Fort Sheridan is maintained by residents that understand its importance and is a true community on The North Shore.

Places to Visit:
Fort Sheridan Water Tower
Fort Sheridan Forest Preserve

Known for its city-like downtown area, Highwood is views as having the best restaurants on the North Shore. Nestled between Highland Park and Lake Forest, this community is close to the Lake and the Metra. An easy commute for those who work in the City, Highwood allows residents to enjoy many different aspects of suburban living. Rooted in tradition, Highwood is known for their festivals, the village of Highwood is always welcoming people of all surrounding regions by creating unique and interesting events.

Highwood Festivals:
Pumpkin Fest
Bloody Mary Fest
Taco Fest

On the border of Cook and Lake County, the town of a Glencoe combines elegant homes with breath-taking landscapes. Brick sidewalks and vintage street lights demonstrate Glencoe’s historic appearance and status. Glencoe is mainly comprised of single-family homes, which include Frank Lloyd Wright architecture and other notable properties.

Places to Visit:
Writers Theatre
Sylvan Road Bridge
Eklund History Center Museum

Twelve miles North of Downtown Chicago, Evanston is rich in history and has been a thriving community since the 1830s. Home to Northwestern University, historic churches and libraries, and a renovated downtown area, Evanston has something for everyone and is considered a great place for people of all ages to live. Condos, townhouses and detached single-family homes are abundant in Evanston.

Places to Visit:
Northwestern University Sporting Events
Block Museum of Art
Merrick Rose Garden

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