Smoking friendly holiday rentals in Downtown Chicago

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!

Great location and amazing property. Clean and cozy! Highly 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.

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

We had a great stay! Amy was super responsive during the check in process when we got a little confused, and she responded within a few minutes which we really appreciated after a long commute. The place was nice and clean, and overall it was a great place to come home to after exploring the city. Definitely would stay again!

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.

Kay - is absolutely amazing and such a sweet host. Very responsive and attentive to my needs and questions. Such a beautiful place to rest and relax.

Lena was the perfect host. very kind, considerate, and accommodating. Thank you for the wonderful stay.

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 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.

A good place to rest after a long day in the city, a bus stop is 3 blocks away and it connects to the orange subway line. Nearby shopping center and very quiet neighborhood, you can even arrive very late on foot. In general, it's perfect for a short stay in Chicago. Thank you Zaine.

I had a wonderful experience, he was very communicative, which was appreciated. There were a few hiccups in my trip that had nothing to do with my stay but being able to communicate with him was helpful. Next time I’m in Chicago I will definitely be booking his place.

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!

Michael’s place was just as described. It is very spacious and fully equipped. It truly felt like home for me, we enjoyed the stay. As a host, he was friendly, responsive and made sure all was well. I definitely recommended urban oasis.

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.

Very responsive, exactly as pictured. The location was great, lots to do. Easy to navigate.