Smoking friendly holiday rentals in South Side

Loved our stay here. a gorgeous home with a ton of space and top notch finishes. Nestled between Lincoln Park and Boystown, this place was the perfect home base for our group.

I would highly recommend this Ari BnB to anyone coming to Chicago. The host Micheal was very polite and flexible exceeding his hosting abilities. He was available 24/7, proactive and very fast in correcting any small issues in a very timely manner. Polite is an understatement as he made me and the others stay there feel like home and an overall great experience. To add, the inside looked exactly like the pictures and clean all throughout. The best part was that the location was very private and peaceful. Thank You, I will definitely be booking again.

Born and raised in Chicago and moved away in 2013. I usually stay with either family or friends when I visit back home, but I wanted some privacy this go round and couldn’t have been happier with this location! It’s in the middle of everything regardless of direction of travel so, it took us no longer than 15-20 minutes to get everywhere we needed to go. There was a small hiccup in checking in, but I reached out to Amy and the hosts were very quick to respond and resolve the issue. I plan on checking this location whenever I come back home from now on. Great spot, Amy!

the host was so nice and responsive. super spacious. the place was nice and had extra amenities. the rooms were nice and it was nice knowing it’s a bed under the bunk bed to slide out. the downstairs neighbor was so nice i loved her. i would definitely book again.

Coty was a wonderful host. There was a slight hiccup with there being no hot water but Coty was extremely responsive and kept me in the loop and got the problem fixed. Highly recommend booking Coty’s place if you’re ever in Chicago. Also the family owned taco spot next door serves really good food and is great after a long day of travel.

Innesa’s home was very nice. We enjoyed our stay and the location was great for walkability and close enough to restaurants and attractions. We would stay again!

Great stay. Host came in the evening to fix cable issue. Appreciated. Location was close to downtown.

The place was very clean the host was amazing! We had a great time here and will definitely come back!

It's hard to get this much privacy and peacefulness this close to the city. Lena's home is a great little hidden gem. The location is amazingly quiet and has a great view of the wetlands below it. Lena became a friend I fell in love with her dog. I wouldn't hesitate to stay here for a day, or a month. It's a great little spot.

Kamau was very responsive and helpful with check In. Clean home and comfy bed. New renovations on the way so hopefully I’ll be back to enjoy those as well!

Clean and kid friendly! Just as described. Perfect place to hang our Easter vacation with our group of 13!! Everyone felt comfortable and accommodated. Only thing I’d change if I could, more pillows! We’re a pillow loving family. Otherwise everything was great!!

She was extremely flexible for our early check in and very nice. She even took it upon herself to get us a refund that was charged by Airbnb

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

I’m giving this Airbnb 5 stars, but I want to be honest about my experience. While the space overall has its positives, there were several issues that left me less than impressed. Pros: The house is spacious with plenty of room for everyone to spread out. Having three bathrooms was convenient, and the kids really enjoyed the small pool table and other games provided. The layout worked well for our group, and the space had potential. Cons: Unfortunately, there were some major drawbacks. The beds had plastic covers, which made them uncomfortable to sleep on. None of the bedrooms had real dressers or nightstands, which made organizing our belongings a challenge. The water upstairs was extremely hot and didn’t seem to have an option to adjust it, which was a safety concern. Additionally, the furniture was noticeably worn down and could use some updates. Overall, the space is cool and functional, but it felt like it needed a bit more attention to detail and care to make it truly great.

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.

great over all will stay again when visiting family

Saurin’s place was super comfortable and felt homely! Location is pretty convenient - with the bus stop / train station being in close proximity. Saurin was super helpful during our stay and prompt in responding to our queries. Would highly recommend his place!

Overall very nice place for the price. Only disappointment was I got to the location listed on the air bnb listing and the actual location was 3 to 4 blocks away which I was a bit upset with. It is closer to the Chicago station on the redline than it is to the river where the listing states. Host was very responsive and allowed me to check out late to avoid waiting around at the airport for a long time.

This has to be the best AirBnB we have stayed at. The apartment was like home from home, super clean and exceeded our expectations. The location of the apartment is a short walk from the L, has everything you need within a 5 minute walk and is in a great neighbourhood. John, the host, is outstanding. Nothing is too much trouble and he gives some great recommendations of local restaurants/ activities. I would highly recommend this apartment if you are in Chicago - we are sure to be back!

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.

Very nice condominium in a great location. We were attending a trade show at McCormick Place and it was about 10 minutes drive. Plenty of room, well equipped and very comfortable. The massage chair was a nice bonus at the end of a long day! Lisa is very friendly, helpful and always available to help with requests or information. Highly recommended!

I was in Chicago for a conference, and Saurin’s place was a few minutes away from a bus stop to get to the venue. The neighborhood is quiet and off the main road, which has a lot to do. Saurin was an incredibly responsive host and I’m thankful for his friendliness and hospitality.