Situated along Lake Michigan’s pristine shores, Highland Park is home to historic architecture, vibrant music venues, serene nature preserves and more. Featured in nostalgic cult classics like “Ferris Bueller’s Day Off” and “Sixteen Candles,” the picturesque town is located just roughly 25 miles from downtown Chicago. Modern Luxury’s editors have compiled our picks for the best Highland Park destinations for shopping, dining and entertainment.
Where To Eat
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493 Roger Williams Ave., Highland Park / Website
This New American hub is the place to go for luxe wine pairings and dinnertime staples like pan-seared branzino, NY strip steak and lemon truffle vinaigrette-topped duck confit salad. Or opt for a sampling of small bites like PEI mussels with Spanish chorizo, Chinese barbecue ribs, grilled eggplant flatbread and more.
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1636 Old Deerfield Road, Highland Park / Website
Get your fill of American fare with a Southern twist at this west-side joint. Dig into specials like tempura-battered Maryland soft-shell crab, pit-smoked barbecue ribs and slow-simmered Cajun shrimp jambalaya.
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675 Central Ave., Highland Park / Website
Try Eastern European staples like pierogis, kebabs, blintzes and borscht at this Ukrainian spot, complete with a sun-drenched patio for outdoor seating. Don’t miss out on chef-led favorites, including beef stroganoff, grilled Alaskan salmon and pan-roasted chicken tapaka.
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617 Central Ave., Highland Park / Website
The second restaurant concept from Highland Park natives Ajit and Sukhu Kalra (Bhoomi) entered the dining scene in May. The contemporary Indian eatery serves innovative specialties like pork belly vindaloo, masala brisket and 12-ounce wagyu steak with spiced herb butter and chimmichutney.
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1888 1st St., Highland Park / Website
Open since 1982, this deli and bakery touts New York-style bagels, latkes, matzoh ball soup, sweet treats (think rugelach, Mandel bread, kiddush cakes and more) and more. Visitors can join for daily breakfast—featuring omelets, blintzes, pancakes and, of course, bagels and lox—and stock up on favorites like corned beef, pastrami, salami and kugel.
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455 Central Ave., Highland Park / Website
Sit on the patio and try popular staples from this farm-to-table spot, including Faroe Islands salmon, black truffle burrata and braised jus short ribs. Stick around for dessert to satisfy your sweet tooth with brownies, housemade crème fraîche-topped berries, ice cream and sorbet.
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581 Roger Williams Ave., Highland Park / Website
Dine family-style or pop in for apps and libations at this Italian restaurant, which boasts housemade eight-finger cavatelli, creamy rigatoni vodka, lightly breaded eggplant parmesan and more. The skirt steak Viaggio is a can’t-miss, crafted with caramelized onions, grilled whole artichokes, roasted red peppers and Chianti wine sauce.
Where To Shop
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1700 Green Bay Road, Highland Park / Website
This Chicago-based, family-owned retailer carries uber-luxe brands like Rolex, Patek Philippe, Cartier, Breitling and more. Visitors can shop for timepieces and fine jewelry, including diamond-inlaid earrings, 18-karat solid gold bracelets and Deepsea, Air-King and Oyster Perpetual Rolex watches, among many other offerings.
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1813 St. Johns Ave., Highland Park / Website
This boutique is the perfect spot to hit up for your next celebration or hosting occasion. Peruse their selection of chic bowls, dinner plates and flatware or elevate your space with lush wool throws, statement vases and inspired glass candle holders.
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662 Central Ave.; 678 Central Ave., Highland Park / Website
With men’s and women’s boutiques just doors down from one another, this on-trend shop is the place to go for activewear, accessories, jeans, tops and more. The two storefronts carry lauded brands like Agolde, Citizen of Humanity, Xirena, Clare V, Marine Layer, Brand New Paige Denim, Vuori and more.
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651 Central Ave., Highland Park / Website
Visit this gallery and gift shop for artisan-made jewelry, home decor, handbags and more. Take home a handblown match cloche, scarves from local designer Isabelle Gougenheim and gemstone-inlaid bezel-cut rings from Austin-based jeweler Jodi Rae, among many other offerings.
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1839 2nd St., Highland Park / Website
Freshen up your home and your style with decor, accessories and apothecary goodies from this designer boutique, located in the heart of Highland Park. Browse items like salt reed diffusers, aesthetic coffee table books and gold-filled bracelets—which make the perfect gift or (well-deserved) treat for yourself.
What To See & Do
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883 Sheridan Road, Highland Park / Website
Relax and rejuvenate at this award-winning private beach, free to residents and accessible to non-residents with daily or seasonal passes. The spot features a nature cove for ecological programming, concessions, a lifeguard-monitored swimming beach and a recreation beach. Visitors can also join for upcoming events like beach yoga, fishing excursions and more.
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1390 Sunset Road, Highland Park / Website
With a freshly completed $7 million renovation and a British Heathland design, this upscale golf club is one to hit up for tee times, leagues, clubhouse eats, tournaments and merchandise, including apparel and accessories. Situated along the serene Foley fishing club, golf enthusiasts can brush up on their skills with private and group lessons or test their aptitude on the course.
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1957 Sheridan Road, Highland Park / Website
Visitors can explore museum-grade exhibitions, partake in art classes and join for upcoming events at The Art Center Highland Park (TAC). The not-for-profit organization hosts summer camps, wellness workshops and drop-in courses for artists of all ages and features a professional exhibition space and three individual galleries.
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200 Ravinia Park Road, Highland Park / Website
Every year, from June through November, this acclaimed outdoor music venue hosts live music performances, events and musical masterclasses. This season, the festival will feature more than 100 acts with artists like The Beach Boys, Norah Jones, Broadway’s Ben Platt and more on stage. Visit Ravinia Festival’s website to purchase tickets and to receive additional information about upcoming events.
See also: The Ultimate Chicago Neighborhood Guide
Photography by: Courtesy of Ravinia Festival
