Chicago’s historic South Side is a crossroads of culture, history, and community. It’s also home to world‑class museums, lakefront parks, architectural landmarks, and one of the most dynamic dining scenes in Chicago.
This summer, the opening of the Obama Presidential Center adds a new landmark to the mix, one that celebrates Chicago’s role in forging a presidency.
Hyde Park and its neighboring areas offer a full day of discovery, and these three itineraries — each built around the new Obama Presidential Center — will help you dive right in. Start planning your perfect visit.
Hyde Park itineraries
A playful, hands‑on day for families
Itinerary highlights:
- The biggest science center in the Western Hemisphere
- Kid-approved activities at the Obama Presidential Center
- A local favorite for pizza and ice cream to end the day
Morning: Breakfast and Museum Campus South
Start your day with a family‑friendly breakfast at Valois, the classic cafeteria‑style spot where “See Your Food” is the motto. Kids love the pancakes and adults love the history — it’s one of President Obama’s favorite Hyde Park haunts.
From there, take a short walk to the Museum of Science and Industry, one of the largest science museums in the world. Families can easily spend hours exploring the hands‑on exhibits: step inside a giant tornado, descend into a coal mine, or marvel at the restored U‑505 submarine.
Midday: Obama Presidential Center
Hop on the #6 bus or take a quick rideshare to the Obama Presidential Center in Jackson Park.
Check out the Children’s Garden, the interactive exhibits in the Museum Building, and the Sky Room, which offers sweeping views of the park and surrounding city. The Center’s storytelling spaces — including exhibits on community organizing and the Obama family’s Chicago roots — are designed to be accessible and engaging even for younger visitors.
Grab lunch at the OPC Café, which highlights local South Side vendors and kid‑friendly options.
More to explore: If you’ve got crafty kids, the Smart Museum of Art and Hyde Park Art Center both offer free hands-on workshops, art-making, exhibit tours, and more on select days throughout the year.
Afternoon: Playtime in Jackson Park
After the Center, walk a few minutes south to the Jackson Park Lagoon and the Wooded Island. At its heart sits the Osaka Japanese Garden, a Japanese garden first established in 1893. Today, it’s a peaceful spot where you can spot birds, turtles, and koi. Jackson Park is also home to several playgrounds for the kids to blow off some steam.
Evening: Pizza and ice cream
End the day back in the heart of Hyde Park with dinner at Medici on 57th, a neighborhood institution known for its wood‑fired pizzas. For dessert, walk a block to Kilwins for hand‑paddled fudge and ice cream.
More to explore: Fill out your family’s Chicago itinerary with this guide on kid-friendly things to do throughout the city.
A day of creative inspiration for arts and culture lovers
Itinerary highlights
- An inside look at a Frank Lloyd Wright masterpiece
- A walk through a Gothic-inspired college campus
- Browsing at the neighborhood’s best bookstores
Morning: Coffee and an architecture stroll
Begin with a latte at the University of Chicago Bookstore and Cafe, then take a self‑guided architecture stroll through the university campus. You’ll be walking in the footsteps of Barack Obama, who taught law at the University of Chicago Law School for more than a decade.
Highlights include the soaring towers of the academic buildings, the stunning Rockefeller Memorial Chapel, and the modernist lines of the Regenstein Library.
Book a morning tour of the Frank Lloyd Wright-designed Robie House, a UNESCO World Heritage Site located right next to campus. The Prairie School design offers a fascinating contrast to the contemporary architecture of the OPC.
Midday: Obama Presidential Center
The OPC’s architecture — designed by Tod Williams Billie Tsien Architects — is itself a cultural experience, with its luminous stone façade and tower inspired by the idea of a “hand raised in hope.”
Explore the Museum Building’s exhibits on storytelling, civic imagination, and community voices, as well as the Center’s stunning landscape design by Michael Van Valkenburgh Associates. Throughout the space, stop to admire the original, site-specific works commissioned from more than 30 different artists.
Afterward, enjoy lunch at the OPC Café.
Afternoon: Literary and artistic Hyde Park
Head back toward 57th Street (about a 15-minute walk or a short cab ride) to explore Hyde Park’s literary heart. Browse 57th Street Books, a beloved neighborhood bookstore tucked beneath the trees, then continue to Seminary Co‑op Bookstore, one of the most respected academic bookstores in the country.
Next, visit the Smart Museum of Art, which features rotating exhibitions ranging from contemporary installations to Asian and European collections. Or check out The Renaissance Society, a free contemporary art museum with thought-provoking exhibits from international artists. Both spots are less than a 10-minute walk from the Seminary Co-op Bookstore.
More to explore: The Hyde Park Viaduct Galleries is a colorful outdoor space featuring the work of 19 different artists along 53rd and 55th Street near Lake Park Avenue.
Evening: Dinner at an Obama-approved hot spot
For dinner, book a table at the Virtue Restaurant, which counts Barack Obama as one of its many fans.
This popular spot is Chef Erick Williams’s celebrated ode to Southern cooking. Savor crisp‑edged shrimp, velvety grits, greens simmered to perfection, all delivered with the gracious hospitality.
After dinner, pop down the street for a nightcap at Cantina Rosa, a colorful cocktail bar showcasing Mexican flavors.
More to explore: Discover more historic neighborhoods on Chicago’s South Side, brimming with vibrant arts, culture, dining, and more.
A day of adventure for outdoor enthusiasts
Itinerary highlights:
- Lots of time on the stunning lake shore
- A bike ride to a waterfront nature sanctuary
- A visit to a historic Japanese garden
Morning: Sunrise at Promontory Point
Start the day early at Promontory Point. Try to catch the sunrise over Lake Michigan as you meander the Lakefront Trail. Spend some time enjoying the peaceful vibe of the waterfront and soak in the stunning skyline views.
Then take a short walk to Dawn A.M. Eatery for creative and comforting dishes like a bacon flight or fried chicken and French toast.
Late morning: Obama Presidential Center
From the lakefront, it’s a quick walk straight south into Jackson Park and the Obama Presidential Center. Outdoor enthusiasts will appreciate the Center’s emphasis on landscape, community gardens, and public green space.
The OPC campus includes new trails, plazas, and gathering spaces designed to connect the park’s historic Olmsted-designed landscape with modern ecological restoration. Inside the Museum Building, check out exhibits on community organizing and environmental stewardship, two themes that resonate with the park’s natural setting.
Make sure to save time to explore the parkland surrounding the Obama Presidential Center — the Osaka Japanese Garden is a highlight. It was a gift to Chicago from Japan for the 1893 World’s Columbian Exposition.
Afternoon: Biking and birding
For lunch, head back toward Hyde Park and dig into the Indian‑meets‑soul‑food comfort classics at Rajun Cajun. It’s a quick 8-minute bus ride on the #28 or #15. There are also Divvy stations (Chicago’s bike share program) near the OPC campus and the restaurant if you prefer a short bike ride.
After lunch, rent a bike from a nearby Divvy station and ride south through Jackson Park’s lagoons, woodlands, and restored prairie areas. Continue to the South Shore Nature Sanctuary, a peaceful lakeside habitat with boardwalks and bird‑watching platforms. This area is especially lively during migration seasons.
Evening: Relaxed dinner and a lakeside stroll
End your day with Neapolitan-style pies at Nella Pizza e Pasta, known for its authentic pizzas and pastas in a relaxed atmosphere.
Afterward, take a twilight stroll back to the lakefront, the perfect way to close a day spent exploring Chicago’s most beautiful outdoor spaces. In the summer, you can stop for a cocktail at Reggie’s on the Beach, a casual waterfront bar with beachy vibes and great views.
