Vacation rentals in South Side

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.

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

Designer Garden Unit in Bridgeport

Welcome to Bridgeport! You're a short walk from the best coffee shops, vintage stores, cocktail bars, art galleries, parks, restaurants, and Rate Field, the home of the White Sox! The neighborhood has so much to offer! Just minutes from Chinatown, McCormick Place, and 10 minutes to downtown Chicago! Be sure to check out my guidebook for recs! I look forward to hosting you! -Free street parking -easy Uber/Lyft 24/7 -easy access to public transit -15-25 mins from Midway -30-45 mins from O'Hare

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!

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!

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

Beautifully Remodeled 2B in Historic Hyde Park

2nd-floor unit with two flights of stairs. Older building with radiant heat managed by the building. Enjoy your stay in this charming 2BR/1BA apartment in Hyde Park. Features a comfortable living area, full kitchen, and cozy bedrooms—perfect for families, friends, or business travelers. Close to the University of Chicago, Museum of Science and Industry, and lakefront parks. Easy access to dining, culture, and public transit. A great home base for exploring Chicago!

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

Peaceful Hyde Park Studio Near UofChi & Nightlife

Stay in the heart of Hyde Park! This cozy 400 sq. ft. studio features a queen bed, 65" Roku TV, full kitchen, and private bath. Walk to the University of Chicago, the Museum of Science & Industry, and 53rd Street’s cafés, shops, and restaurants. Easy access to Metra, CTA buses, and the lakefront make exploring Chicago simple and convenient. Perfect for solo travelers, couples, or weekend getaways seeking comfort and style in a vibrant, historic neighborhood.