Holiday houses in Woodlawn, Chicago

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Open floorplan, hardwd floors, stainless appliances, 2 Smart TVs in bedrm & living rm, in-unit laundry, and private parking space. Features a cozy reading nook and large outdoor patio. On a quiet treelined street - minutes from Hyde Park and waking distance to Lake Michigan, Jackson Park Golf Course, the 222,000sq ft Regal Mile Film Studios, and upcoming Obama Presidential Library. Your stylish home away from home!

Charming 2-bdrm near University of CHI Campus

Perfect for business travelers, healthcare professionals, and U of C affiliates, this newly renovated and fully furnished 2-bedroom, 1-bath apartment offers comfort and convenience. Located on a peaceful, tree-lined street in the vibrant Woodlawn/Hyde Park neighborhood, the unit features modern amenities including an in-unit washer and dryer, high-speed Wi-Fi, and a dedicated workspace. Public transportation (Metra + CTA) is just steps away and downtown Chicago in just 15 minutes by car.

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate office/baking space and front half is your private Airbnb suite. There is no kitchen in the unit. This Airbnb is in our 4-unit apartment building and next door to our house where we've had a 5-star Airbnb room for 9 years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

Lux amazing Stay on University of Chicago Campus

Tastefully decorated 3-bed, 2-bath apt on the renown University of Chicago campus , 11 min walk to CCD & Bernard Mitchell Hospitals and Main quadrangles, and a 5 min walk to a grocery store. Offers office space, Chef’s kitchen, in-unit washer/dryer, Nespresso, TV in every room, and fast WiFi. Ultimate luxury living! We believe that everyone should have a place to call home. Therefore, 15% of our profits are donated to homeless students who attend Malcolm X College in Chicago.

Cozy Apt~Location near UChicago & Lake Shore Drive

Welcome to Woodlawn, a charming neighborhood just minutes away from the Obama Library. My home is located in a historic area with local shops and beautiful buildings that offer a true Chicagoan experience. Here are some features you'll love: 6-min drive to the Obama Center, 15-min to downtown, newly renovated interior with keyless entry, CTA bus line nearby for easy transportation, excellent investment opportunities, historic Woodlawn neighborhood, and free street parking.

Comfy Solar & Green 2BR Near Hot Hyde Park!

Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

Beautiful 3BR/2BA Penthouse

This is 3 bedroom 2 bath condo located in Woodlawn on the confluence of Hyde Park, walking distance to the University of Chicago and a 15 minute drive from downtown! The condo includes custom cabinets and fixtures, hardwood floors, stainless appliances, quartz counter-tops, fireplace, In-unit washer/dryer, walk-in closet in primary suite with professional closest organizers throughout, double vanities in bathrooms, and a rear deck. Exterior parking is also included.

Classic Den @ U Chicago

Our homey space includes full bath, kitchenette, living area and super comfy Queen bed. Direct access to unit from the exterior rear door makes coming and going easy. Located on University Ave. just a minutes walk to U. Chicago campus, easy access to public transportation taking you downtown in just over half an hour. *Note*This is in the basement of our home. Interior stair door locks from basement side to ensure guest privacy. You will hear us upstairs at times.