Apartment holiday rentals in Woodlawn, Chicago

This was a great stay! The place was in a great location - not too far from downtown but in a peaceful neighborhood. Super comfortable and convenient. Would definitely stay here again!

Ruby was a kind host. Gave a tour so I could see where everything is and clearly explained the location, parking, etc. The place has more amenities than I remembered. I was only there for a couple nights but would be great for a longer stay. Lots of space for community and privacy with your party. Very walkable and close to Hyde Park and University of Chicago. Totally recommend.

Next to the trains, a apartment with separate bedroom, living room, kitchen and bathroom, even a laundry room available if necessary and a host who responds quickly and does not hesitate to give advice on Chicago. I highly recommend!

Great stay, carmen was very responsive and the place is very modern and clean.

I deeply enjoyed my stay, easy instructions, got the hang of the room well, cozy and nice for you or 2 people. it was very clean and the kitchen and bed area were pristine. I definitely recommend.

I enjoyed my stay! Marjorie was a great host and I felt at home. Everything was at a short distance and the location was great! Definitely recommend!

Very nice place to stay. Michael was a great host. area is walkable, within 1 mile of university of Chicago, museum of science and industry and South shore/metra.

Very nice space and Eric was very responsible when we had questions.

Christopher’s place was perfect for our needs! The place was very roomy, the kitchen and bathroom was spotless and spacious, and the bed was comfortable. The neighborhood was quiet and calm with more than enough easy and free parking. The metro was less than a 10 minute walk which was perfect for us getting in and out of the city easily. They also allowed us to drop off our luggage before check in hours which we greatly appreciated. Needless to say, we enjoyed our stay and would strongly recommend staying here.

Over the last 3-4 years we have stayed at Ian’s at least 10 times while visiting our son at Uchicago for football games and graduations. It is a very clean and welcoming place to stay. We have enjoyed this Airbnb so much we have recommended it to underclassmen families to use and keep up our tradition. Ian has been more than accommodating for us to book and has responded very promptly when asked for favors. Overall, I would give it a 10/10!

Large, clean, and cozy space. The neighborhood was very nice and quiet. We had access to a grocery store just a couple blocks away. It was easy to catch an uber wherever we needed. Host was very communicative and sent us local recommendations for our stay. It was perfect for our weekend trip. ☺️

Nice residential neighborhood. Good easy parking. Very clean. Exactly as pictured on the listing. Perfect location for our Chicago vacation and to attend our daughter’s location from UChicago.

Charming Victorian house in a peaceful and safe neighbourhood. So thankful for the really comfy queen bed - felt like my home mattress!

Just wonderful. That was one of the most beautiful accommodations I've ever been to. The apartment is totally lovingly furnished. Everything was super clean and tidy. There are even toothbrushes, toothpaste and a sleeping mask, if you need them. The kitchen is also super equipped with everything you need. The short walk to the metro was also very convenient. We would definitely come back.

Lovely basement studio in very nice neighborhood. Easy drive to nearby neighborhoods or downtown area. Highly recommend if you’re looking for a comfortable stay!

Kendal is a superhost. The apartment is as described. Enjoyed staying at this apartment. Very near to supermarkets, McCormick convention centre and public transport. Highly recommend.

We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.

What a spectacular stay! We thoroughly enjoyed our time at Stephanie's "Areal Oasis". Apartment was spotless, well decorated, very well furnished, and the view is spectacular. Stephanie was an excellent communicator and always very responsive. We thoroughly recommend staying here and hope to return.

We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.

I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.

SPECTACULAR!! This space is how you should visit Chicago. Breath taking views from this 33rd floor luxury penthouse apartment lives up to the hype. Our family of six were extremely comfortable in this 3 bedroom/3 bath unit. And for a person that likes cooking, the kitchen is spacious. Don’t pass on seeing Chicago from the views in this beautiful apartment.

The host is very helpful. The house next door seems to be abandoned; therefore, there is a lot of trash and broken glass on the floor next to this building. The place is very chic and fun. My favorite part was the bath bar and back yard. There are no dishes only cups and coffee mugs no paper towels and no plates. I liked the fact that the host asked questions before approving our reservation. I will definitely reserve again.

Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.