Vacation rentals in South Side

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Florence Room - 3min to CTA, Free Parking, Roomy

The Florence room is one of three rooms in the grotto. The room has a king size bed and full size sofa sleeper for a maximum guest count of 4. You will have access to the kitchen for the microwave, toaster, and stove, along with free Keurig coffee. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms.There is a private mini fridge in your room for food storage. The house is one block from the Kedzie Green line rail station.

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.

A8- 6 min Walk to Pink Line

Located at Pilsen which is one of the 12 Coolest Neighborhoods around the world (by Forbes) this is a Private bedroom with a full size bed bed in a share apartment close to Downtown Chicago (around 15 min by car). Great gastronomy around. Accesible public transportation just 6 min far by walk to the train (Damen Pink Line) We made a very detailed listing so you can know exactly what to expect, don’t book before reading the whole advertisement.

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Cozy newly renovated apartment in Bridgeport

Welcome to your perfect home away from home in Bridgeport, Chicago 🏡 This newly renovated cozy 1-bedroom, 1-bathroom apartment offers a comfortable, inviting space just 10 mins to downtown Chicago. Located couple minutes from Chinatown Whether you're here to catch a White Sox game or immerse yourself in the vibrant local food scene and culture, this location is ideal for exploring the best of Chicago. FREE PARKING 🅿️ NO PARTIES.

Spacious & serene in hip spot. Sleeps 4.

Located in the heart of Pilsen, a vibrant neighborhood rich in Mexican arts/ culture, and an emerging hipsterville. Check out art gallery crawls, award winning restaurants and local taquerias. Thalia Hall (3 blocks away) w/ indie and major musicians. 7 mins via car to downtown or 2 blocks to train/bus. Mask wearing is optional. Guests are not required to wear masks. Chicago Registration #: R21000069179

Entire Home in Bronzeville

Modern 2-story condo in the heart of Bronzeville! Enjoy 2 bedrooms, 2 baths, and an open living space with a fully stocked kitchen. Upstairs, relax or play a round of pool in the loft game area. Minutes from Downtown, McCormick Place, and Lake Michigan. Perfect for families, friends, or business travelers looking for comfort, style, and fun in one of Chicago’s most historic neighborhoods!

Private Spacious Room in a shared house.

House located in Calumet City, not far from Franciscan Hammond hospital, 10 minutes away to Ford Plant, 19 minutes away to Horseshoe Casino, 18 minutes away to the BP Plant and Purdue University. Dining area and family room with television and WiFi. These areas are shared with other guests. Private room has a full bed, tv, closet and office desk and mini fridge.

Chicago River Room, near 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.

Fresh and Sunny Bed & Bath by UofC

Our private bed and bath offers high ceilings, a sunny Juliet balcony, comfy Queen bed and fresh, clean finishes, including an airy, open shower. Use us as your base for exploring the city or work as we are steps away from both public trans. and the University of Chicago. It's hard to find a more convenient location in Hyde Park! Welcome!

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.