Holiday rentals in South Side

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Lux New Hyde Park Apt by UChicago, Museum of S&I

Welcome to Your Luxury Hyde Park Retreat — Just Steps from History, Culture & UChicago Luxury 3BR/2BA apartment in a fully renovated historic Hyde Park ground floor apartment. New renovation with high-end finishes, in-unit laundry, dedicated workspace, and Peloton. Located just 1.5 blocks from the Obama residence, approx. 0.5 miles to the University of Chicago, and about 1.5–2 miles from the Obama Presidential Center. Ideal for families, groups, or professionals seeking comfort and location.

Simply Sleek & Uneek: Mins To/Fr D'Town Chicago

Simple Sleek Minimalist 1-BDR Condo at the Crossroads of Bronzeville, Kenwood & Hyde Park: Situated at the intersection of historic Bronzeville, elegant Kenwood, & culturally rich Hyde Park, this 1-BDR, condo offers a peaceful retreat just minutes from downtown Chicago & the Lake. Featuring a large living room, fully equipped kitchen, & private bathroom; designed with your comfort & convenience in mind. It's an ideal home base whether you’re visiting for work/business, school, or a getaway.

Sunny Penthouse - Oakwood Beach

Gorgeous top-floor 2-bedroom, 2-bathroom condo in the heart of Bronzeville! With high ceilings and tons of natural light. The fully equipped kitchen has everything you need to cook a delicious meal, or you can enjoy one of the many great dining options nearby. 🌊Take a 15-minute walk to the lakefront and Oakwood Beach. Centrally located near: • Downtown Chicago • Soldier Field & Guaranteed Rate Field • Field Museum & Art Institute • Chinatown, Hyde Park & Pilsen • And much more!

Modern Hyde Park Studio near UofC

Modern, spacious garden studio is perfect for a solo traveler or couple visiting Chicago. Comfortable queen bed and full pull out sofa. Quality linens, pillows and towels. Make simple meals using the provided microwave, mini fridge, toaster oven and single cup coffee maker and tea kettle. Dishes, glassware and silverware provided. Dishes can be washed using a provided dishpan, soap and sponge. Noise: airborne and impact noise. Contact for MTR rates for business travelers/professionals.

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

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

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.

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

Modern 2BR/2BA Condo | Spa Bath + Free Parking

Enjoy the entire condo to yourself in this clean, modern 2-bedroom, 2-bath home, designed for comfort and convenience. Perfect for couples, families, or business travelers seeking a quiet, cozy stay. Enjoy a full kitchen, spa-style bath, and free street parking. Minutes from UChicago, McCormick Place, Soldier Field, Shedd Aquarium, and quick access to I-90, Lake Shore Drive, and downtown Chicago.