Holiday houses in Woodlawn

2 br, 2 bt, UChicago Coachman's Guesthouse

This 2 bedroom, 2 full bath, stand alone UChicago Coachman's House sleeps 5 comfortably. Less than 1/2 mile to the UChicago main quad. Situated on a quiet residential street. Full kitchen to prepare your own meals and dedicated laundry. Easy access from O'Hare or Midway airports. Less than 2 blocks from the Metra train to downtown, Mccormick Place, Soldier Field, Wintrust Arena, Grant Park and Millenium Park. Walk to Trader Joe's, Walgreens, restaurants, lakefront, stores, museums and more.

*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.

Serene retreat near Obama center & public trans

Escape to our unique historic bungalow in South Shore. Perfect for architecture lovers, this serene retreat is designed with peace and comfort in mind. Features a dedicated office, and three outdoor spaces, including a private yard with a fire pit. Just minutes from Lake Michigan, the childhood home of Michelle Obama and the Obama Presidential Center is minutes away. The Museum of Science & Industry, 3 beaches & golfing are nearby. Your private, and peaceful getaway awaits.

UChicago Condo | 2 Baths, Private Parking & Entry

Enjoy the convenience of a dedicated private parking space with direct access to your own private entrance. This upgraded and spacious 1-bedroom, 2-bathroom condo near the University of Chicago features hardwood floors, stainless steel appliances, in-unit laundry, two Smart TVs, a cozy reading nook, and a large outdoor patio. Conveniently located near Hyde Park, Lake Michigan, Jackson Park, and the Obama Presidential Center. Perfect for extended stays and remote work.

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

WoodlawnLUXE 4 Bedrooms

WEEKLY AND MONTHLY DISCOUNTS!!! Enjoy this newly renovated LUXE 4 bedroom 1 bathroom condo on the entire second floor of a two flat building! All bedrooms have LG Smart TV'S! Located with a 5 minute drive to The University of Chicago, Hyde Park, The Cultural Center, The Dusable Museum, and the new Obama Library. A 30 minute drive to Midway airport 45 minute to Ohare. Chicago’s downtown, McCormick Place, and museums 30 minute drive. Located 4 blocks to Greenline Line

Beautiful Penthouse (Near Obama Center, UChicago)

This is 3BR/2B condo located in Woodlawn on the confluence of Hyde Park, walking distance to the University of Chicago and a 15 min drive from downtown! The condo includes modern and new appliances, fireplace, In-unit washer/dryer, walk-in closet, double vanities in bathrooms, and a rear deck. Couch is also a pull-out bed for living accommodations. One designated parking space is available for Airbnb guests, with free street parking also available.

2 15 min to Downtown Next to UniversityTrain Park

☞ 1 Smart TV ☞ Fully equipped + stocked kitchen ☞ Self check-in ☞ Luggage storage available ☞ Onsite washer + dryer in basement ☞ Air conditioning 》35 mins to airport 》15 mins to Downtown Chicago 》 Minutes walk to train station 》 Walking distance to University of Chicago 》 Across street from parks Minutes walk to train station 》2 bedroom, 1 bathroom 》Sleep 6 If you need additional bedrooms please reach out we other units in the same building

Modern Eco Stay • UChicago • Parking • Backyard

Relax in this eco-friendly South Side retreat designed for comfort, style, and convenience. Located minutes from UChicago, Hyde Park, Jackson Park, the Museum of Science & Industry, and the lakefront, this unit is perfect for families, medical visits, students, and anyone exploring Chicago. With a private entrance, free parking, and a large fenced backyard, this modern space gives you privacy and peace in the city.

Lux Modern 3BR on UChicago Campus & Hospitals

Welcome to The Brown House — a bright, spacious 3-bedroom, 2-bath home just minutes from the University of Chicago and major hospitals. Ideal for families visiting students, medical professionals, and groups seeking comfort and convenience. Enjoy fast WiFi, a fully equipped kitchen, in-unit laundry, and easy self check-in. Free street parking is available across the street, with parking passes provided if needed.

Luxe Loft vibe | King Suite |4BR 3Ba

Stay in style near Chicago’s best! This luxe 4BR, 3BA loft is perfect for families, professionals, or UChicago guests. Enjoy a king suite with jacuzzi, 3 queen bedrooms with desks, and an open layout with smart TVs, exposed ducts, and dining for 10. Walk to the Obama Presidential Center, Museum of Science & Industry, and lakefront. Adjacent to Hyde Park with quick downtown transit—just 50 min to Indiana Dunes!

Sleek Apt near U of Chicago!

Come stay at our inviting apartment, minutes from the University of Chicago and hospital! Ideal for families, students, scholars, and travelers. Sleeps 6 (1 twin memory foam floor mattresses and 1 pull out couch). Free street parking! Explore nearby: Museum of Science and Industry, Robie House, golf, lake, and Hyde Park's charming shops/eateries. Easy public transport to Downtown Chicago for city adventures!