Pet-friendly vacation rentals in South Side

Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

We enjoyed our stay. Clean, nice house, and in a location convenient to everything we wanted to do. Host was very responsive when we had questions. We loved being so close to the train. Great restaurants around, and also a convenience store and Family Dollar right around the corner for anything you need!

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

We had an excellent stay here. hosts went above and beyond to make sure we had everything we needed. beautiful house and parking spot was ideal.

I enjoyed staying at Rich's place. If you want to fish, the calumet river Greenway isn't far, and it's easy access to I-57 N/S too.

Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.

The house is very beautiful. My family and I loved the place and how spacious it is.

Great place to accommodate a big group. Close enough to the city if you don’t want to be in the heart of the city. Responsive host

We had a fantastic stay at this beautiful stay in downtown Chicago. The views were absolutely incredible! The home gave us a breathtaking look at the city skyline, day and night. The location couldn’t have been better, as it was right in the middle of everything, with restaurants, shops, and attractions all within pretty good walking distance. The unit itself was spotless when we arrived and had everything we needed. The bed was super comfortable, and the space felt both modern and welcoming. It was the perfect spot to relax after a day out exploring the city. The host was also very responsive and helpful!! Would definitely recommend this place to anyone looking for a clean, comfortable, and stylish stay in downtown Chicago. We’d happily stay here again!

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.

Excellent place to stay, easy access to highway, quick ride to downtown

Kevin and Kayla’s unit on W Diversey Ave was a cozy and convenient spot for our Chicago trip. The space was clean, well-equipped, and had everything we needed, with quick access to buses and the Blue Line. The only minor downside was some occasional dog-walking noise from the unit above, but as it has already been mentioned before, it is to be expected. Mattresses were a bit wobbly for our tastes but it's a matter of preference. Overall a great, cozy place on a very convenient location in Chicagoland. What really stood out was Kevin’s excellent hosting—he went out of his way to make us feel at home, regularly checking if we needed anything, and was quick to help in-person when we had a small hiccup on our last day. Super responsive and friendly and a true host!

The place was spectacular. The views are breathtaking. My family and I loved the place.

Great value for a work trip! Easy to find, convenient amenities, and Patty was very proactive with a clear, easy check-in. Would recommend for a small group.

Very comfortable accommodations, Newly renovated and safe on street parking. All in all a great stay for a graduation weekend.

For basics, it is very clean and comfortable with a well appointed kitchen, comfortable beds, and easy street parking. The space itself is remarkable. Patterned tin walls and ceilings, a triangular shape, nicely decorated, and the construction details from converting it to an apartment are all in keeping with the style. We loved it.

Me my freinds and family enjoyed our stay. The host was very quick to respond to any concerns. The home was clean and spacious. The decor was nice to take pictures. I liked that it had a bathroom downstairs for easy assess. We will come back when we visit Chicago again. Thanks you guy you were awesome.

This was an excellent stay on the south side of Chicago. A beautiful quiet neighborhood with plenty of parking on the street. In addition to the garage that is already available in the property. Wonderful was able to help me with any of my needs and he went above and beyond, even adding a desk to the property when I asked. I stayed for three months for school, and was sad to leave after. This Airbnb had everything I needed even things that I usually travel with or not necessary because he provided them such as an air fryer, cookware, and even a squatty potty! I was so happy at this Airbnb because of the host and also because of the location. The community there is wonderful, and I felt safe every day. I even walked around and met people in the neighborhood and spent a lot of time there. It was quiet on the weekends and accessible to the downtown area.

Terrific apartment, and spotlessly clean. We were only 2 people, but it had a king and a queensize bed in 2 separate bedrooms, as well as a comfortable and well dfurnished iving room. Very modern and up to date.. Kitchen was ample and well equipped and stocked with basic staples. We didn't meet our josts ut they were responsive to our messages.

I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.

Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.

Quiet and friendly neighborhood. Very walkable. Place had everything I needed for the stay. Will definitely return if I’m ever in the area again.

We loved staying in this building and area. Don’t sleep on the amenities - the skydeck and lounge are really nice. Easy parking nearby w spothero. If you’re up for walking, it’s doable to walk to The Chicago Theatre or downtown. Good communication w hosts via the Kasa link they send you.