Holiday rentals in South Side

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Chicago Post-Punk/Industrial Museum Apt • 3BR

Live inside Chicago's post-punk/industrial story • museum-themed 4BR in Bridgeport. Vinyl, posters, fast Wi-Fi, easy parking, 12-15 min to McCormick/Loop/Sox This unique 2000sq ft apartment is full of authentic music memorabilia, art pieces, vinyl, cassettes, books, and curated design making this part of Chicago's Industrial history. Set in vibey Bridgeport (96/100 walking score) – books, vinyl (2), coffee (6), pizza (4), dive bars (3), restaurants, art spaces & more all within walking distance

Luxury Condo | Spa Bath | Full Kitchen | FREE PRKG

Enjoy a luxurious escape in this modern Bronzeville home where style meets comfort. Designed with contemporary finishes, cozy textures, and a serene vibe, it’s perfect for couples, families, friends, or business travelers. Easily accessible to UChicago, McCormick Place, Soldier Field, Shedd Aquarium. With quick freeway access to I-90 & Lakeshore Drive, Downtown Chicago is just minutes away! Relax, unwind, and enjoy free street parking plus all the essentials for a premium Chicago stay.

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!

Charming 1BR/1BA Apt in Chicago

Welcome to this charming 1-bedroom, 1-bath apartment nestled in one of Chicago’s most desirable neighborhoods. This cozy unit blends classic character with modern updates, featuring hardwood floors, large windows, and a bright, functional layout. The kitchen offers updated appliances and plenty of cabinet space, while the bedroom provides a quiet, comfortable retreat. Enjoy easy access to local cafes, parks, shopping, and public transit—perfect for city living with a touch of charm.

Designer Hyde Park Studio • Walk to Shops & Lake

Escape to this stylish Hyde Park studio near the University of Chicago, Museum of Science & Industry, and Lake Michigan. Perfect for solo travelers or couples, it features modern décor, a comfy queen bed, smart TV, and fast WiFi. The kitchenette is stocked for light cooking, and everything you need is within walking distance—cafés, restaurants, and shops. Enjoy easy access to downtown Chicago by train or bus for sightseeing, dining, and exploring the city’s vibrant attractions.

McCormick332, Chinatown, SOX, GrantPark, UC

Feel free to check us other listings: https://www.airbnb.com/h/zengarden001 https://www.airbnb.com/h/zengarden221 https://www.airbnb.com/h/zengarden331 https://www.airbnb.com/h/zengarden333 A new renovated luxury zen garden step to Chicago loop, McCormick Place, Millennium Park, Navy Pier, SOX, Art Institute, UIC, IIT, UCHICAGO, Chinatown(hundreds of delicious food), Midway Airport. Perfect place for everyone in Chicago! Super easy free street parking!

The Chicago Cozy Brick Retreat

This unit offers a charming blend of modern amenities and historic charm. This thoughtfully designed unit features an open-concept living space with exposed brick walls and stylish furnishings. The fully equipped kitchen boasts new appliances, perfect for culinary adventures. The comfortable bedroom, with a cozy bed and ample storage, ensures a restful stay. The sleek bathroom includes contemporary fixtures and a walk-in shower. Street parking is easily available.

Chicago River Room near Resurrection Med Ctr

R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.

Private BR;Parking by UofC/HydePark

This comfortable condo is a stones throw away from Hyde Park and University of Chicago. The space is great for visiting parents, researchers or professors. Your room features wifi, and a 32" TV. Access to the"L", Uber, close to lake, 20 minutes from downtown (depending on traffic). Room can accommodate 3 (4 in a pinch)

Private room w/bath in urban canopy

Private bedroom w/attached private bath in a gorgeous 3-bedroom/2-bath apt on the only curvy street in Hyde Park. Common entrance and living spaces, shared with an artist who uses two bedrooms - one as studio. Enjoy the lush light-infused top floor of a turn-of-the-century urban tree house.