Smoking friendly vacation rentals in Downtown Chicago

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.

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.

My son and I felt so absolutely comfortable here! And any issue we did have (only about how the TVs worked) we was helped instantly very quick response! Felt so very welcomed! So super clean! With so many extra amenities. Will stay here every time I visit my son in Chicago

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!

I really enjoyed this Airbnb.. The host was amazing and her place is BEAUTIFUL 😍

Greg was very accommodating! If you’re looking for a stress free place to chill this is the spot :) The space was clean and easy to get to.

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.

Gary had great communication and local recommendations. Unfortunately, it wasn't what we were looking for but the price was worth having a place to rest.

No problems - good host. Was able to do my own thing and just come back when needed. Trains are about a 10 minute walk away

Justine and her 2 kitties were wonderful! Great kitchen and large bedroom. Would 100% recommend to anyone staying in Chicago! Absolutely great experience!

I had such a great time at the Hacjenda House! I came here with my dog for a peaceful getaway and it was exactly that. Lena set up the fireplace inside for me and I was cozy all night. Plenty of firewood in their backyard. Super spacious and beautiful inside and out. Their tub upstairs is also so spacious for a bath. Lena was so kind by checking in on me throughout my stay. I didn’t want to leave. I definitely want to come back.

I wasn't sure what to expect but this was a very comfortable pad. I had no issues finding the place and Davi took time to come acquaint and give me the lay of the land once I checked in. I felt right at home and it was relatively private for me even though it had shared spaces. I will definitely rebook here if the need arises again. All in all, great host, great location and great price. Tony

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

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.

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!

My families stay at this airbnb was great! Looked exactly like the pictures, felt cozy, clean, secure and safe. For what we came to Chicago to do the location was perfect! Michael gave great suggestions for places to visit and if I had a question he responded promptly. He checked in several times to make sure our stay was going well and I myself appreciated that. I will most definitely be staying here again.

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!