Condo holiday rentals in South Side

The hosts are great—very responsive and accommodating. It’s a lovely space, with a fully functioning kitchen and very walkable to a close cta stop that’s a quick 30 minutes downtown. Area around the place is lower income, so if you’re not used to being in a city, you maybe feel less comfortable. Would recommend if you’re comfortable with urban environments though!

We enjoyed our stay at Mackson’s place. We were out and about the majority of the time during our stay, but were able to relax in the evenings in the condo. The condo is in close proximity to a local park which was nice. We traveled with a baby and brought our own pack-n-play for the baby to sleep in. There was plenty of room for the pack-n-play in the bedroom. If we have another event in that area, we’d book again.

David is a great communicator and check in/check out was easy. The apt was clean and comfortable. Having a designated parking space was also very helpful! Thank you David!

Thomas is an amazing host! He was very proactive in communicating right from the start of the trip ,was very welcoming and warm. This Airbnb house is spic and span. It is very clean , beautifully decorated and has everything you need to be comfortable in a home. The Kitchen is stocked with all vessels , has basic pantry supplies and has a gas for cooking warm meals. Thomas and his wife were also very thoughtful and considerate and left us a basket full of snacks and coffee pods - that was a really sweet gesture from their end.The coat closet has umbrellas , incase you need one , which I thought was very considerate as well. Thomas also regularly checked in on us to ensure we had a smooth stay - his check in and checkout instructions were uber clear and made it possible to check in and check out without any hassles. There is a starbucks and a bunch of small restaurants on a 10 - 13 min walk from the house.Overall , I would highly recommend his house to other guests.

This was the best property we've ever stayed at. Everything was as advertised or better. Darryl answered all our questions in a timely fashion and even had the place ready a little before our scheduled check-in to accomodate our flight schedule. The neighborhood is excellent, very safe and quiet. We never had to park more than 50 feet from the front door. Everyone's first impression was "This place is huge" and it was actually even better than the pictures indicated--and the pictures indicated it would be great. Absolutely would look to stay here any time we are in Chicago and looking for something south of downtown. Would recommend to anyone looking for a place in the area. Easy commutes to downtown or Hyde Park and ride shares always arrived within 10 minutes.

Great quiet stay! After having another host cancel the day before checking in I found Keeva’s place and I must say I’m happy the other host cancelled because staying here was perfect! Also that massage chair was everything !

Great space and location for our time in Chicago for our daughter’s UChicago graduation

recently had the pleasure of staying at Carlton's Airbnb in Chicago with family - 4 adults. We couldn't be more satisfied with my experience. From the moment we arrived, we were impressed by the cleanliness and attention to detail throughout the property. The decor was absolutely beautiful, creating a warm and inviting atmosphere that made me feel right at home. The beds were comfortable. Additionally, the convenience of parking was a huge plus, making it easy to come and go without any hassle. Overall, this Airbnb met my expectations in every way. I would definitely stay here again and highly recommend it to anyone looking for a comfortable and stylish place to stay in Chicago.

The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.

We were staying in Chicago for a concert at Soldier Field. It was extremely walkable and easy to navigate. The condo is just right with the 2 bedrooms and king sized beds. The provided keurig coffee machine and coffee was nice. Easy walk to Roosevelt station for local transportation.

My dad and I were on a baseball road trip and this was a perfect place for a cubs game! About a 15 minute walk. Will was responsive and friendly, and the place might have been one of the coolest bnbs. Such a fun and relaxing spot. Would easily stay again!

Our stay was fantastic. We have three children and everyone was comfortable. The location was perfect, the hosts were clear communicators and quick to respond. We would stay here again in a heartbeat.

Great location, and easy access to all main streets. The neighborhood is quiet, and very safe. The people in the neighborhood were very welcoming. The condo was nice, very spacious and a great value for the cost.

One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!

This is a WONDERFUL one bedroom apartment that is both private and spacious! The owner/host has the space fabulously decorated with an eclectic mix of original contemporary artwork and antiques. Nothing is generic about the space and it has been outfitted for guests with loving care. The host, Kaye, clearly puts much trust in her guests with her charming decor and furnishings. The amount of space, the privacy and the home-y feel make it a place we'd love to return to.

Great neighbourhood! Susan was very communicative and a great host. Highly recommend.

I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.

Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.

Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.

Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

You can walk to Northwestern University, and the surrounding environment is clean, comfortable, and pleasant.The house is fully equipped, and I love cooking in the kitchen.Our whole family had a wonderful week here.Would stay again.

Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.