Smoking-friendly holiday rentals in South Side

Loved our stay ! Would love to stay again !

Was a great place. Never would have thought you could raise farm animals in the middle of Chocago, but it was cool to see. It is close to some train tracks and has that farm smell, but neither were that bad. Would definitely stay here again!

Loved our time here. The location is perfect and the few issues at check in were quickly resolved by Amy and team. Would definitely come back here.

Ms Denise was awesome, very helpful . The studio place was very clean complimentary Snacks and toiletries. She care about her guest, very helpful with night life restaurants and travel to city. Definitely recommend

Jerry's place was fantastic, easily one of the best experiences I've had with any of the short term vacation rental companies. I can only say that I wish more were as kind and accommodating as Jerry. The place was well appointed, with new, comfortable furniture. I would absolutely stay again.

I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

Great property. Host was very extremely responsive and helpful with any questions I had. I will definitely do business here again once I return to Chicago!

Great place for our short stay, comfy beds

Me and my wife went here for our pre honeymoon and had a great time. Lena has a great house and very private from the community. Truly amazing place and you can see the river from inside the bedroom.

We stayed for 2 months during home renovations, and rehabilitation from surgery. The home was just what we needed for our family of 5 and 2 dogs. It was welcoming, comfy and perfect in size. The host were great to work with as we had to extend our stay several times until our home was finished. The beds were so comfy, and those pillows were amazing.

They was great people and i will stay again thank you both for having us and treating us well i didn’t even have to ask for the codes upon check in they sent it ahead of time

Highly recommended looks way better in person !

The host was very responsive and helpful she really made the stay feel as if me and my girl were at home while we threw a little club themed get together for my girlfriends birthday it was great enough space and beds I would most definitely book again in the future and would recommend worth every penny I paid

We really enjoyed our stay here. House is conveniently located near many places and restaurants. The neighborhood felt safe. They were so helpful when it came to checking in. We got there early and went on into the city and I didn’t realize it was gonna take two hours to get back-and-forth between the city and the house with traffic, so they met me later that evening to let us finish seeing everything we wanted to see in the city before driving back. I absolutely love older homes so l was really excited when l seen all the charm this home had to offer. Intercoms was a huge plus as it fascinated the kids. Plenty of room for our two families to move about. Would stay again.

The space was great for Christmas family gathering. The home was spacious and clean, with plenty of bedrooms and a nice kitchen with updated appliances. Joyce was a gracious host and very accommodating to my last minute reservation needs.

Amazing spot, great price, and very guest friendly. Place was nice and had plenty of points of interest near it.

great host and stay! saurin gave us plenty of recs, allowed us to check in early and leave our luggage because we had later flights. spacious room with ample amenities. blue line and a few buses all <10 min walk away. saurin was always very friendly and made himself available to help if we ever needed something

gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.

This was truly one of the best Airbnb experiences I’ve ever had. From the moment I arrived, everything felt warm, welcoming, and thoughtfully prepared. The space was not only beautiful and impeccably clean, but it also had so many special touches that made it feel like a true home away from home. What made this stay exceptional, though, was the host. They were incredibly kind, attentive, and genuinely cared about making my visit as perfect as possible. Every question I had was answered so promptly, and they offered wonderful local recommendations that made my trip even more memorable. It’s rare to find someone who goes above and beyond with such sincerity, but that’s exactly what this host did. I left feeling not just like a guest, but like a friend. I am so grateful for this experience and would return in a heartbeat. Highly, highly recommended to anyone considering this stay — you will be in the very best hands!

I had a really great experience staying at this Airbnb. From the moment I booked, the host was extremely responsive and helpful, answering all my questions quickly and clearly. The check-in process was smooth and easy, which made a great first impression. The space itself was very clean, well-maintained, and exactly as described in the listing. You can tell the host puts a lot of care into making sure guests feel comfortable. The bed was cozy, the amenities were thoughtful, and everything was stocked and ready for use—just like a home away from home. The location was also convenient, and I felt safe and relaxed throughout my stay. Overall, it was a very positive experience, and I would absolutely recommend this place to anyone looking for a stress-free and pleasant stay. I would definitely book again in the future!

Great location and amazing host! Super walkable area that’s also close to the train. Saurin has a bunch of local recommendations and is very friendly. The room was also much bigger than expected!

I feel lucky to stay at this place during my 2 month visit to Chicago. Barbara and James were amazing hosts, always caring and making sure their guests feel at home. They were also super helpful about everything a first-time traveller needed to know, from weather to transportation, food to community events. The apartment itself was cozy and lively, way beyond what it seemed on the photos! A variety of apparatus made a seamless transition to life in Chicago. Meanwhile, a Walgreens was within 15 mins walk. A Trader Joe’s and a Target within walking distance. The neighborhood is peaceful and diverse. Nearby, there were top restaurants of Mexican, Peruvian, Vietnamese, Indian, Middle Eastern, Greek, Haiti cuisines, just to name a few. Public transit was extremely convenient to either downtown Chicago or Evanston. Despite the possibilities to adventure, living expenses were easy manageable. Because of Barbara and James, I had an unforgettable and amazing journey at Chicago.

Saurin was a wonderful host! Super helpful and the place is in a wonderful location!