Pet-friendly vacation rentals in Woodlawn, Chicago

This was a fantastic stay! The space was beautiful, spacious, clean, and well located. Definitely a great option if you're in the area and need a larger space.

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!

Very nice place very big only things is there was only one bathroom, With a lot of people that can get pretty cramped , Adam was very responsive and understanding!

House is centrally located . Clean. Host was responsive. 100% recommend this property !

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

Michael was a great host. Very responsive and friendly. The property was exactly as described. Very clean and looked just like the photos

We stayed for almost a week with three dogs. Sarah's place was perfect for our needs - great backyard, comfortable beds, clean and equipped kitchen, and awesome location - close to Chicago, Indiana dunes and easy to navigate thru, no traffic. Sarah and her family (and their amazing dog Chandler) are super friendly and helpful. We will definitely stay there again once back in the area.

Overall great for our stay, Fairly close to a lot of things.

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

Cool building in a great location. Everything was quite nice. Really liked the layout which provides enough space for two couples to have privacy.

This was a perfect stay for an amazing weekend getaway and Festival experience. The area was walkable and had several great options for food and bev. Free street parking directly in front of the property, secure garden level access, and all the instructions and guidance were well laid out. Additionally, they had a guidebook that was well put together and everything was cohesive and exactly as pictured and described in the app. John was very responsive, friendly, and he and his family provided a perfectly appointed environment for our getaway… And their dog, Star 🐶 was such an angel! We had a great time, thank you!

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.

⭐️⭐️⭐️⭐️⭐️ An unforgettable stay in the heart of the city! This Airbnb was absolutely amazing! The location couldn’t have been more perfect right in the middle of everything, with easy access to restaurants, shops, and public transportation. The space was spotless, beautifully decorated, and felt like a true home away from home. Our host went above and beyond to make sure we had everything we needed. Their hospitality, local tips, and quick communication made our stay even more enjoyable. You can tell they genuinely care about their guests’ experience. If you’re looking for a comfortable, stylish place to stay with an incredible host in Chicago, look no further. We’re already planning our next trip back!✨

My family of 5 including my elderly parents had a lovely stay at Rachel and David’s house for our son’s graduation from UChicago. It is in a quiet location that is very close to the university. The hosts were very friendly and flexible. The place is spacious, light and airy and extremely clean. The beds (especially the two large bedrooms upstairs) had usually comfortable beds. All in all it a 10 out of 10!

Great stay, Both host were very great communicators, helped out with ANY thing. This house was BIG too big for my party very spacious nice interior, nice decor. If I was to visit Chicago, IL again this would be my stay, Thanks to the host for making my trip comfortable and fun.

my friends and i stayed at Bosede’s lovely home for sueños festival weekend! it was lovely very quiet neighborhood. we had everything we needed from towels and shampoo/conditioner/body wash to extra blankets or pillows! we all enjoyed our stay and Bosede is a great host!

This is my second (maybe 3rd?) stay at one of Jordan & Jeremy's properties and the experience is consistently pleasant. Listing is accurate, place is cozy and clean. I wish all AirBnBs were this consistent!

Un lugar bonito. Está algo alejado del centro pero si rentas un auto, está excelente para poder moverse. Los espacios son muy adecuados y limpios.

Cornell was very thoughtful as he made sure we were staying hydrated in the extreme heat he was very welcoming I felt straight at home and he was also very nice and friendly which made it easier to get along with and talk to him! He is a great host and if I find myself ever coming back to Chicago, I’ll make sure to go through Cornell if I need a place to stay for the trip!

Lovely apartment, perfect for the 4 of us. Kitchen is wonderful and well stocked, beds are comfortable, and bathroom was clean and had everything we needed. Just a 5 minute walk to the Metra train station or bus stops that will take you anywhere you would want to go. Would stay again and do recommend!

I had a wonderful stay