Smoking friendly holiday rentals in South Side

Daniel’s place in Lincoln Park was spectacular. The location is prime. The accommodations were perfect for my large family. Easily walkable. He was a great host.

it is super close to where we needed to be and the host was easy to get a hold of if anything came up. very quiet neighborhood, we would definitely stay here again when we attend another concert.

Had a blast staying here! The mattress was super comfy and the nightstand with the charger was a lifesaver. Loved chilling on the patio with the string lights. The place is super close to the West Loop but still quiet. The host knows the city well and was quick to respond. Would definitely stay 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!

Pamela was very helpful and had quick responses.

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.

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!!

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!

We had an absolutely wonderful stay, Rameez was very helpful! We utilized the space for a post wedding get-together and it was perfect! The kitchen is nice and open, the living room is a great size, and the game room provided wonderful space to spread out. The locations of the rooms were great because they're all on different floors. The bathrooms are in wonderful locations, clean, and updated. There was space for 4 parking spots. There is greenery to allow a dog in the backyard. Rameez even got Walmart to deliver needed supplies to the house during out stay. It is a newer Airbnb so it's clean and Rameez obviously wants to help create wonderful memories. Certainly would recommend the house and would recommend if you need a large space.

Lena rolled with the punches & communication. She was very responsive and very passionate about what she is creating. It’s a flip but the accessible part is done lovely & when it’s finished will be even more serene! Only complaint? LENA! I couldn’t even get the lock & turn! Lolololol make it easy for us old folks. Looking forward to staying again!!

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!

We enjoyed our stay at this house . She was very responsive and she made good use of space in the house to accommodate a family. Would recommend to anyone.

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

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

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.

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!

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.

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.

We really enjoyed our stay at Lisa's lovely place. Lisa is a wonderful host, reaching out to us multiple times before and during our stay in order to ensure that we had the best possible experience. The beds and furniture are very comfortable, and we loved the shower. The main TV is exceptional, and allows you to watch live TV from areas all over the country along with many subscription sports channels. Parking was no problem thanks to the private gated parking lot.

We had a really good time in Saurin's place. Thank you for being so welcoming!