Holiday houses in Woodlawn

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

Modern Apt Near U of Chicago!

Stay here in our warm apartment, a stone's throw away from the University of Chicago school and hospital! Ideal for families, scholars, students, vacationers or business travelers. Sleeps 6 (2 twin memory foam floor mattresses available). Free street parking! Close to Museum of Science and Industry, Robie House, golf courses, lake, grocery and charming streets of Hyde Park. Great shops and restaurants! Public transportation close by to travel into the city and explore Downtown Chicago as well.

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.

*Hyde Park *2 Masters *2 Living Rooms *Courtyard

Welcome to our newly renovated retreat, The Urban Oasis in Hyde Park. Embrace the artful decor throughout the spacious house only a 10 minute walk to the nearest beach. Rent a bike for a scenic ride to nearby attractions like University of Chicago, Obama Library, Museums, the Natural Walkway Nature Park and the lake. Conveniently located near Hyde Park central to downtown Chicago, this is the perfect stay for families and small groups as you explore everything Chicago has to offer.

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, UChicago, Jackson Park Highlands & Golf Course • Free designated 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.

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.