Holiday houses in Ravenswood, Chicago

Allen's place is great, I stayed for five days and loved it! My highest compliment is that it's super well-equipped, to the point it feels lived-in (in a good way). For example, the kitchen is stocked better than mine, you'll find it easy to make a meal here. The rest of the unit is well thought out, too. My one piece of advice is to pay reallyyy close attention to the check-in instructions. There are multiple entrances to the complex, and they look similar. You might end up trying the wrong lockbox 10 times if you're not careful :) Overall, I highly recommend this place! Friendly neighbors as well!

We had a great stay with Matt! He was very communicative and flexible with check in which was really appreciated. The place was as described and in a great location - so many places nearby to explore. Matt put together a guide with local recommendations which was really helpful - we visited one of the recommendations twice because it was that good. The unit has everything needed for a comfortable stay and was clean. Will definitely stay again when back in town!

This was a nice place to stay and Demitri was a wonderful host! The apartment was close walking distance from the brown line train at Western and that made it easy for us to get around when we were unfamiliar with the area. Any time we had questions Demitri was quick to respond and wished us well. We had all our bags from the airport the day we were going to check in and he worked with us and allowed an earlier checkout time to help us out. Great experience and would stay again!

We had a lovely stay here! Nicholas was so helpful and responsive, and the place was perfect. The studio is immaculately kept, and we were very comfortable. The neighborhood is beautiful and a short walk away from public transportation to get anywhere you want to go. My favorite part of this place is the luxurious bathroom— so nice for cleaning up and relaxing after spending the day walking around the city! Highly recommended!

Wonderful unit and had everything we needed to be comfortable with our family (and small children). Sarah was extremely thoughtful and considerate, even pulling out baby furniture based on our kids ages before we checked in. Was also super responsive and helpful. The rental is in a convenient location. Street parking can be tight, but even at its busiest was able to find something within a block (and there's a loading spot right next to the apartment).

Kathleen's place is such a find! I come to Chicago yearly to visit family and I've stayed in a number of Airbnb's. This was my best stay ever for a number of reasons. Kathleen's place is nicely laid out and so comfortable. Kathleen is so accommodating and responsive. She allowed me to check in early and when I left my purse in a rush to catch my Uber, she communicated with me immediately. Her patio is an absolutely oasis and I enjoyed spending time out there with my family. The neighborhood is wonderful. There is a great little restaurant right next door and so many things within walking distance. Her place will always be my first choice for a place to stay when visiting Chicago.

Very nice stay. Apartment was neat clean and simple. Good location close to train. Great parking host gave good simple instructions. I have a very nice stay. You do have to climb some steps to get to the apartment but it’s not bad. It was a quiet comfortable location.

This guesthouse was absolutely stunning and the entire stay felt like a warm exhale. The space was peaceful, private, and designed with such clear intention. Every detail felt like quiet luxury, from the open, light-filled layout to the serenity of the patio, hot tub, and pool area… down to the elegance of the kitchen and bath amenities. The neighborhood is calm, walkable, and close to everything I needed; but honestly, I barely wanted to leave. When I retreat, I look for spaces that feel like sanctuary; places where I can land, create, and come back to myself. This one did exactly that. Jon was a wonderful host. He was responsive, kind, and generous with his time when I needed help. You can feel the care he’s poured into the space. I left feeling more grounded, inspired, and restored than when I arrived… which, in my opinion, is the highest compliment. Would absolutely stay again!