Pet-friendly vacation rentals in Woodlawn, Chicago

We stayed for a week with 2 children of 8 and 10. The place is larger than we expected; which is nice. The street and neighborhood are both really nice. Train is close; which is very handy to visit the city. Close to Lincoln park and many restaurants and shops. This place was very comfortable, private and quiet. Brian was also also very flexible with check in and check out times. Definitely recommended !

The home was beautiful. And I love the master bedroom I felt like a queen walking into the room private bathroom. Big backyard. Everything was fabulous and next time I go back I will stay there again if available.

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!

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!

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

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.

The location is perfect for getting to any part of Chicago. It's within walking distance of endless activities, and within one to two blocks of multiple "L" and subway lines that will take you anywhere. You are staying in the middle of the city, so you will hear the train and sirens throughout the night; however, the host provides disposable ear plugs which were very helpful. I had no problem sleeping throughout the night. Front desk staff is always friendly. The host is very responsive, and courteous. Washer and dryer in unit helped me with not having to pack as many cloths for my trip. Everything was spotless upon arrival. Would absolutely 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.

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

We had a wonderful stay in Chicago with our infant and toddler! The check-in process was smooth and easy, which made settling in stress-free. The apartment was clean and cozy, with fresh sheets, a spotless bathroom and bedroom. The kitchen was fully stocked with all the essential utensils made it convenient to prepare breakfast for the kids. One big plus was the parking, the detailed video provided made it super easy to find the exact location without any confusion. The location of the apartment was fantastic within walking distance to Willis Tower and surrounded by great restaurants. It was also just a short 15 mins drive to major attractions like the Shedd Aquarium, Adler Planetarium, and Navy Pier. Everything we needed was already available in the room, we didn’t have to call out or ask for anything during our stay. Overall, a comfortable and convenient stay for families traveling with little ones. Highly recommended!

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.

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

From the moment we arrived, everything about this Airbnb was spot on. The listing was 100% accurate—from the layout and amenities to the beautiful decor and serene location. What you see in the photos is exactly what you get (and maybe even better in person). What truly made our stay stand out was the host’s genuine hospitality. They were incredibly responsive, proactive with communication, and went out of their way to make us feel at home. Thoughtful touches like a personalized welcome note, and real care for our comfort and experience. The place was spotless, well-stocked, and every detail had clearly been thought through. Whether you’re here for a weekend or a longer retreat, you’ll feel cared for and completely at ease. Highly recommend to anyone looking for a reliable, welcoming, and exactly-as-promised Airbnb stay!

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!

Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I

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.

Host was super responsive and helpful. The place was good, we had no major concerns. We enjoyed our stay!

Five star stay all around. Great location, near a nature reserve. Large living room and bedroom, lots of amenities. Cornell supplied excellent directions and instructions. Super easy to communicate with. Thoroughly enjoy the stay. Would love to book again, but calendar is full and I know why - this please is great, Thank you Cornell!

this is our second time at James place. it was great the first time and great the second time. The apartment is comfortable, inviting , spacious and has all you need for the stay. Bathrooms are clean. Kitchen is well equiped. access is easy. Parking on street is easy. Grocery is nearby. it is pretty close to uchicago campus so it is perfect isf you are visiting that area. James is a very responsive host. I hope it is a available when we visit our daughter next!! I would take it again!!

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!