Holiday rentals in South Side

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

Trendy and Comfortable Stay in Hyde Park

Requires walking down 5 steps. Street parking is not guaranteed, we recommend using ride share apps. Experience the charm of this cozy apartment in historic Hyde Park. Featuring a comfortable living space, fully equipped kitchen, and stylish touches throughout, perfect for relaxing after a day in the city. Near the University of Chicago, Museum of Science and Industry, lakefront parks, restaurants, you’ll enjoy the perfect blend of culture, history, and convenience during your Chicago stay.

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transit - 5 min walk Lake - 10 min walk Obama Presidential Library - 1.8 miles University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles McCormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, access to expressways to get anywhere in the city.

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!

West Loop Urban Chic Coach House

Welcome to this historic neighborhood in Chicago, a cultural tapestry, rich in history and bursting with energy. Enjoy strolling along the streets lined with historic buildings, savor diverse culinary delights. Bronzeville is not just a place to stay; it is a community experience Enjoy, this one-bedroom, full bathroom historic coach house with a full kitchen, smart TV, and dedicated living space. Unwind in comfort with an in-unit washer/dryer. Plenty of street parking available.

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.

Studio Bronzeville 42 - 1BD/1BA APT Near Downtown

Studio Bronzeville 42 (SB42) is a cozy retreat in the heart of the historic Bronzeville neighborhood, conveniently located just 5 miles from Downtown and minutes to Hyde Park, the lakefront beach, and the upcoming Obama Presidential Center (opening June 2026). This charming and bright one-bedroom apartment suite features art from the owner’s private collection, is on the lower level of an attached row home, and includes a king-size bed, full kitchen, and in-unit W/D.

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.

Studio in Hyde Park Near UChicago & Lake

Enjoy Hyde Park living in this bright, newly updated 400 sq. ft. studio featuring a cozy queen bed, 65" Roku TV, full kitchen with essentials, and private bath. Walk to the University of Chicago, the Museum of Science & Industry, and 53rd Street’s cafés, shops, and restaurants. With easy access to Metra, CTA buses, and the scenic lakefront, this charming space is perfect for comfort, convenience, and a true Chicago experience.

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

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.

WoodlawnLUXE 4 Bedrooms

5 minutes to Obama Center and University of Chicago! 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 4 bedrooms have LG Smart TV'S! 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