
Private suite holiday rentals in South Side
Find and book unique private suite rentals on Airbnb
Top-rated private suite rentals in South Side
Guests agree: these private suite rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for private suite rentals in South Side
Family-friendly private suite rentals

2 King Beds /Easy Downtown / Free Str Parking-Read
Beautiful home, and easy access to the house. With nice bars and easy transportation near by to the city. Michelle was a wonderful host, would stay here again.

A guest suite centrally located, but so quiet
We had a lovely stay at Cinda Jo’s home. One note: Be careful if you are tall, as ceilings are low. Otherwise, the attention to detail, decor, full kitchen with nice appliances and host provided croissants were all over the top wonderful. The space was cozy and warm, and felt like home. When we left Cinda Jo wanted to make sure all went well and we had a nice chat before taking off to the airport. Recommend highly.

Tropical Bungalow Getaway in Quiet Neighborhood
This is our second time staying at this listing. The location is perfect, close to portage park and several great restaurants. It’s the best night sleep I’ve ever gotten at an Airbnb - the bed is so soft and comfortable, and the bedroom is so quiet (which, as a garden level apartment I usually expect a little noise). This is just a really great place to stay. I highly recommend it.

Private suite in Lincoln Square
This Airbnb was one of the best we have stayed in. Extra touches such as handrail for the stairs, night tables on both sides of the bed, plenty of books for a rainy day, and great instructions for doing laundry. Thanks so much for sharing your home! Patricia Otto

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
Jamie was a really amazing host! She was friendly, helpful, caring and went over and beyond to make sure me and my kids were comfortable and had everything we need. Gave us lots of great recommendations to restaurants and as a first timer in Chicago she made sure I was aware of the traffic and other helpful information! My kids LOVE her she was vey nice, patient and gentle with them. Kid friendly house/area VERY quiet. The beds are the BEST after a long day of traveling very comfortable. The place was beautiful very nice decor and nicely maintained. We will definitely be staying here on our next visit to Chicago.

Cozy, Quiet, Garden Getaway!
Beth’s place was a great spot in a beautiful, peaceful Chicago neighborhood. The Logan square area was close by and easy to walk to. Beth gave us some great recommendations. The location is also walking distance to the brown line if you would like to get to the city! The garden apartment looks exactly like the photos and has everything you would need for a short/longer stay! I also liked the quiet street it was on, safe and FREE to park your car. Would love to come back!

Wrigleyville/Boystown/Entire Private Floor!
Very accommodating! Close walking distance to Wrigley Field and several restaurants. Recommend Steve's place and would stay again!!

The Deer Suite
Private little oasis. The exact stay we needed. During a long road trip.
Private suite rentals with a patio

Comfy suite w/ steam shower near McCormick Place
We had such a wonderful stay at Felicia’s place! From the moment we arrived, it was clear how much care and attention she puts into hosting. Felicia was absolutely lovely, friendly, welcoming, and always quick to respond to any questions we had. The interior of the space was beautifully designed and clean. We felt at home here, highly recommend staying here.

Comfortable and Cozy Suite in Quiet Neighborhood
Alexis was a great host! The place was so cute and cozy and wasnt far from downtown (besides traffic ofc.) The street itself felt safe, but more of the surrounding areas felt a little more risky. Other than that I enjoyed it and highly recommend!

The Hidden Beach House
This stay was peaceful, yet SO CLOSE to everything! My partner and I wanted a weekend getaway for his birthday, and this was the perfect place to stay. Lincoln park was a short walk away, yummy restaurants, and walking/uber distance to downtown like the Bean. The location was everything!!Caid was also very responsive which made the process stress-free.

Logan Square’s Garden apt style rental
Desiree is a great host and is very friendly and welcoming. We were lucky to have found this spot.

Logan Square Chicago 2BR cottage, close to it all!
My friends and I stayed here for a weekend trip and Elizabeth's place was perfect! Check in was easy and the apartment was well-stocked and clean. Communication was also great as Elizabeth made sure that we had everything we needed. The neighborhood felt very safe, and the blue line was a quick walk away for easy access to downtown.

2BR Logan Sq Mini-Resort stay + Pet friendly
We liked that the kitchen was fully stocked with cutlery, dish-ware and cookware. It was nice having a washer and dryer for our dirty clothes. Laundry supplies being provided was nice. Although we had our own, the fact there were toothbrushes and tooth paste was awesome. The bed was comfortable. We enjoyed our stay,liked the property and look forward to staying again down the road.

The Dugout in Wrigleyville!
Responsive and hospitable hosts with a fantastic location just a couple of blocks from Wrigley. One note that didn’t bother us: You can hear footsteps from the upstairs unit. Something to beware of if you’re a light sleeper.

Old Irving Park- Sweet Garden Suite with Spa
Very Clean. Very nice neighborhood. Walking distance to train stop. 40 minute train ride to big attractions like Shed. That’s for a couple who has zero experience using public transit efficiently. Great hot tub. Friendly neighbors that we barely noticed. Super comfy bed. Wish we brought our pup but decided against it last minute. Only recommendation would be a few additional climate control options. But 99% cozy and comfortable as is!!!!
Private suite rentals with a washing machine and dryer

BnB on Grace Street - Modern 2-Bedroom Guest Suite
We had a great weekend. The host was incredibly helpful and responsive. The property was clean and a perfect size for our family of four. Great location, close to public transportation, quiet neighborhood, etc. We will definitely be back.

New Bright & Airy Entire Unit in Logan
It is a great place, had everything I was looking for, would definitely stay there again Thanks!

Travelers Retreat in Old Town Chicago
We had a great experience. Celia was very accommodating and communicated with us fast if we needed something. She even provided us with a list of fun activities and local restaurants that she could wholeheartedly recommend. The location is especially nice. It was really peaceful and quiet.

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln
Sue and Bill's place is a gem! The apartment is truly unique and the hosts have thought about practically everything that a guest would want/hope to want during their stay (communication was superb). The queen bed is incredibly comfortable (Tempurpedic) as was the futon bed. Cozy apartment with the 5ft. wall dividing the sleeping area from the "main" living area allows a little privacy. The apartment is in their home's basement, but there are windows and the lighting inside with ceiling/wall lights makes the space very bright and cheery. Large walk in shower, towels, linens were lovely. Parking is in the rear of house off the alley. The yard has sitting areas with a lot of yard art. There are a few stairs down to the basement and a walk through Bill's stained glass workshop (fascinating). Walk-able neighborhood with many restaurant choices. They also had so many local recommendations for sight seeing that we have to come back! We highly recommend this place as unique and special.

Spacious Garden Unit • Private Entry + Parking
Great place to stay with friends or as a family. One bedroom has a queen sized bed. The other has two twin beds. Restroom right in the middle. Kitchen was stocked with plates, silverware, etc. The hosts also had books and board games available. No complaints!

Contemporary, private suite w fireplace
Carin was the sweetest and the apartment was the cutest! Not too much and not too little.

Adorable studio style unit - Self check in ⚡️
Peter's place was a nice studio to stay in while doing work in the North Shore area. It's located next to a lot of restaurants and a CVS and is in a very nice neighborhood. I really appreciated the soft bed and the shower was luxurious. I also appreciated the size of the fridge and the convenience of the kitchen. I also appreciate how prompt and professional Peter was. I had an urgent issue come up during my trip and he very promptly and professionally solved the issue. Two things I would keep in mind with thisnbooking: yes, you can hear the upstairs Airbnb guests. Usually this consisty of movement around the house, but there was a time when a phone alarm went off in the top unit and it woke me up. Additionally, the room lets in a lot of light, so if you are a light sleeper this may be an issue for you. Finally, the floor is more sloped than it appears in the photos. This was not a hindrance to ne at all, but it may affect other's experiences. Overall, this was a very nice Airbnb.

Gorgeous Studio 15 Minutes From Ohare!
Edward was great, and our stay was super convenient thanks to his thoughtfulness. The space was tidy and had everything we needed!
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Bed and breakfasts South Side
- Rentals with a washing machine and dryer South Side
- Apartment rentals South Side
- Rentals with breakfast South Side
- Family-friendly rentals South Side
- Waterfront rentals South Side
- Rentals with lake access South Side
- Flat rentals South Side
- Rentals with a fireplace South Side
- Rentals with a hot tub South Side
- Rentals with an EV charger South Side
- Rentals with beach access South Side
- Rentals with outdoor seating South Side
- Smoking-friendly rentals South Side
- Rentals with a firepit South Side
- House rentals South Side
- Pet-friendly rentals South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with a patio South Side
- Rentals with pools South Side
- Private suite rentals Chicago
- Private suite rentals Cook County
- Private suite rentals Illinois
- Private suite rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club