Vacation rentals in Jackson Park, Chicago

South Shore Dr Retreat

Enjoy easy access to everything from this perfectly located home base. Walking distance to a 9 hole golf course, beach, and famous Lake Michigan lakefront bike and walking path. Commuters dream with easy access to Chicago bus line and Metra train station. You are close to the following Chicago locations: Lake Michigan lakefront path La Rabida Children’s Hospital 63rd Street Beach Museum of Science and Industry Obama Museum(opening planned in first half of 2026) University of Chicago Hyde Park

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. 1 min walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Quiet Comfort of Home

Kick back and relax in this calm, stylish space located in a historic neighborhood 1.5 miles from Hyde Park. The back door leads to a comfortable back yard with seating for eating, sunning and grilling. Lake Michigan beaches are 6 blocks away, and you can walk to the Obama Presidential Center, Griffin Museum of Science and Industry, University of Chicago, and Japanese Garden. Public golfing is near. To get down town, there are 3 buse lines on the corner, the Metra train and the bike path.

Historical Basement by Jackson Park; Metra/Parking

Stay in our historical XIX Century home in Chicago's iconic African American district! Imagine living like locals in this up-and-coming neighborhood. Enjoy: • Proximity to Hyde Park, Lake Shore Drive, Starbucks, market, laundromat, fast food • Steps to Jackson Park Hospital • 22-min Metra train ride to downtown • 15-min drive downtown • Close to Obama Presidential Center, Museum of Science & Industry, Jackson Park Highlands & Golf Course • Free designated parking

Trendy Studio in a Vibrant Area

This trendy studio apartment offers modern, open-concept living in a vibrant neighborhood. Filled with natural light, the space features sleek finishes, a stylish kitchenette with contemporary appliances, and a cozy sleeping nook. The compact bathroom is equipped with modern fixtures. Located just steps from cafes, restaurants, and shops, this apartment offers both comfort and convenience, making it the ideal urban retreat for those seeking a dynamic lifestyle.

Washington Estate minutes from University of CHI

Kick back and relax in this calm, stylish space. The Washington Estate is the professional escape. We provide a 1-bed/2-bath to accommodate a maximum of two guests. Everything you need, full kitchen, WIFI, exercise room, in unit laundry and exterior patio seating for your enjoyment. Gated parking available upon request. Near the historic Hyde Park, the University of Chicago and 8 minutes away from Lake Shore Drive. Walking distance from public transportation.

Peaceful Hyde Park Studio; Near UChicago & Lake

Welcome to our cozy Hyde Park studio, perfect for 2 guests! Just minutes from the University of Chicago and the beautiful lakefront, this space offers comfort and convenience in one of Chicago’s most historic neighborhoods. Explore the vibrant 53rd St strip filled with cafes, shops, and local charm. Whether you're here for study, leisure, or a bit of both, enjoy a peaceful stay in the heart of Hyde Park.

The Modern Woodlawn 2 Bed 2 Bath

Enjoy a stylish experience at this centrally-located place. Minutes from University of Chicago, the upcoming Obama Presidential Library, Golfing at the South Shore Country Club, Lake Michigan, Public Transportation and Downtown Chicago. There is an ALDI grocery store around the corner. Jewels Grocery Store is a few minutes drive by car. Free Street Parking.

Hyde Park 2BR, Near Museums & UChicago Med, 20%Off

Comfortable 2BR flat in South Hyde Park near UChicago Med, Midway, and key museums. Restoration toward a classic 1920s feel is ongoing, and we’re still settling in— but the space is quiet, stocked, and thoughtfully set up for real travelers. Fast WiFi (200+ Mbps), USB ports, wireless chargers, and beds that outdo most Airbnbs—and many hotels.