24 hours in Chicago’s South Shore neighborhood

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Named for its location along the Lake Michigan shoreline, South Shore was once one of Chicago’s fastest-growing neighborhoods. The success of the nearby 1893 World’s Fair and land availability next to Jackson Park prompted quick land sales and a housing explosion.

The first community established within South Shore was the exclusive Jackson Park Highlands in 1905. The innovative community comprised exquisite stately homes with expansive lots and large manicured front yards. South Shore established its luxurious Country Club the following year. More diversity in residents and architecture came about in the 1920s with the construction of modest single-family homes and apartment buildings.

Today, South Shore is rich in history and beautiful architecture. Residents and visitors alike enjoy the beautiful lakefront, culture, and eclectic mix of dining options. Looking to spend 24 hours in South Shore? Here are a few things to seek out.

Start your day in a cafe

Every day of exploration should begin with coffee.South Shore Brew coffee shop is a neighborhood staple serving coffee and bites in bright and spacious surroundings. Choose from various coffees, teas, smoothies, and pastries to get the day started. They also offer a few heavier breakfast bites.

Chef Sara's Cafe in South Shore
Chef Sara’s Cafe in South Shore

Prefer a heartier start to your day? Then payChef Sarah’s Café a visit. Chef Sarah, who started selling food out of the back of her truck, has created a cozy, welcoming café known for its homestyle breakfast and brunch.

Visit a historic Chicago landmark

South Shore Cultural Center (formerly South Shore Country Club) is a Chicago landmark encompassing 65 acres of lakefront green space. The Mediterranean-Revival style interior houses a solarium, grandiose ballroom, and theatre that features marble, wood paneling, chandeliers, and ornate details. The beautiful structure is where Michelle and Barack Obama chose to hold their wedding reception. In addition, the Chicago Parks Department hosts various programs and events at the cultural center throughout the year.

South Shore Cultural Center

Outside the cultural center, the grounds include a butterfly park and nature sanctuary. Visitors can walk along a boardwalk near the beach to observe dunes, wetland, prairie landscape, and wildlife. In addition, the park includes a beach and a nine-hole golf course with panoramic views of the lake.

Also in the South Shore neighborhood, Rainbow Beach and Park totals 142 acres and offers breathtaking views of the city. The fieldhouse provides a gymnasium and fitness center. Outside, the park’s green space features Chicago’s last surviving Victory Garden, basketball, tennis, and handball courts, baseball diamonds, and two playgrounds.  

Lunch at a neighborhood favorite

Refuel with lunch at Majani Soulful Vegan for plant-based recreations of Chefs Tsadakeeyah and Nasya Emmanuel’s favorite heritage and family recipes. Both vegans and non-vegans will be impressed by the numerous menu options prepared with a plant-based spin.

Mary Jane Café, Chicago’s first Black-owned CBD-infused café, is known for its grilled cheese sandwiches and offers wraps, smoothies, and desserts. Word on the street is that the peach cobbler is a must. Diners can request food items with or without CBD.

The Foodie Spot delivers fresh, quality food made from scratch with love. Menu items include burgers, wings, biryani, and famous bean pies, all with an emphasis on organic ingredients. 

Admire the beautiful architecture and history

Many notable architects were involved in the development of the South Shore community, so there’s a treasure trove of historic gems there.

South Shore is home to one of fourteenHistoric Bungalow Districts in Chicago, containing homes recognized for their historical, cultural, and architectural significance. Developed by 35 different architects, the bungalows in South Shore are a mix of frame, stucco, and brick structures exhibiting a natural variety of forms, textures, and colors. Most homes were built between 1911 and 1920, with the last completed in 1931.

One of the most architecturally significant homes in the area is the Allan Miller House. Built in 1916, this Prairie-style home is the work of John Van Bergen, a colleague of famed architect Frank Lloyd Wright. This Chicago landmark home is the only surviving Van Bergen residence in the city.

Nearby, the stunningBryn Mawr Community Church, built in 1915, was an early commission of architect Andrew Rebori while under mentor Jarvis Hunt. The original chapel is in the Italian Renaissance Style. A limestone-clad Gothic addition was designed in 1921 by the architectural firm of Lowe & Bollenbacher.

Elegant Jackson Park Highlandsis South Shore’s premier neighborhood. Architectural styles include Classic Revival, Queen Anne, Dutch Colonial, Tudor, and Craftsman, to name a few. Designated a Chicago Landmark District in 1989, Jackson Park Highlands is one of Chicago’s most attractive historic neighborhoods. 

Immerse yourself in culture

In the evening, catch a comedy show or R&B concert at South Shore’s cultural treasure, theETA Creative Arts Foundation. Take in a Friday night Jazz show atThe Quarry Event Center, or admire the artist exhibitions and DJ sets atStony Island Arts Bank.

There’s no shortage of exciting things to see, do, and eat in the South Shore neighborhood. So today is a good day to start planning your visit!

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