Holiday 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.

Quaint Apt near UChicago, Wifi + Parking + Laundry

Unwind at our stylish and cozy 3-bedroom, 2-bathroom apartment located just steps from the University of Chicago in the vibrant Woodlawn neighborhood. The space features, an open-floor plan, hardwood floors, a fully equipped kitchen, plenty of natural light. It's the perfect place for a family or a group of friends who want a quiet place to relax while still being close to food, fun and tourism in Chicago. Ideal for family vacations, group trips, traveling professionals or students.

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

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.

Zen ~ NBY Beach, Golf, DT, Quiet, 1425 sq ft

Discover this renovated historical Chicago bungalow nestled in the cultural South Shore neighborhood. ~ Michelle Obama's childhood home and school are nearby ~ The block is the origin of the Back Alley Jazz community festival ~ Museum of Science & Industry ~ Garden of the Phoenix ~ Nature trails & Beaches ~ Jackson Park Golf Course ~ South Shore Cultural Center ~ Nearby access to bus/train, beaches, and free street parking

A Stones Throw from U Chicago South Campus!

This 2 bedroom garden unit located in vintage World's Columbian Exposition era building, it's been renovated and updated. You can't get much closer to the University of Chicago campus. This quiet garden unit is within walking distance of lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.

Private BR;Parking by UofC/HydePark

This comfortable condo is a stones throw away from Hyde Park and University of Chicago. The space is great for visiting parents, researchers or professors. Your room features wifi, and a 32" TV. Access to the"L", Uber, close to lake, 20 minutes from downtown (depending on traffic). Room can accommodate 3 (4 in a pinch)