Condo vacation 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!

My family and I stayed at Lisa's place while attending my son's graduation, and we enjoyed our stay. Lisa and her team are pleasant, helpful, and attentive. And the unit is clean, spacious, well-appointed, and centrally-located. We found it easy to travel to and from UChicago via car in under 10 minutes, so attending graduation activities was a snap. I wouldn't hesitate to recommend Lisa's place, especially if you're headed to Hyde Park or Bronzeville.

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.

Thomas was a wonderful host who truly went above and beyond. He gave us excellent recommendations for vegetarian restaurants, which we really appreciated. It was our first time visiting Chicago, and Thomas’s support throughout our trip made a big difference. The Airbnb was thoughtfully stocked with everything a guest might need—even umbrellas! Highly recommended.

We enjoyed our stay at Iman's place. It was very clean and had the right amount of space for a weekend away from home. The beds were comfortable and we had everything we needed.

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 !

If you're looking for a place in Chicago that is gorgeous to stay in with easy access to public transit, this is it! The hosts were super helpful with recommendations and quick to answer with any questions. I would definitely stay there again!

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

Great location right next to the train station and walking distance to lakeside. Well stocked apartment, king beds were very comfortable. Host was quick in addressing an issue with AC unit. Very nice stay in a good location in downtown Chicago, we thoroughly enjoyed the convenience and comfort of the place!

I stayed at John’s Airbnb during my trip to Chicago, and I honestly couldn’t have asked for a better spot—especially being right in the heart of Chinatown. The place was spotless, super cozy, and had everything I needed for a comfortable stay. You can tell John takes pride in keeping it clean and well-stocked, which I really appreciated. What made it even better was the location. Chinatown in Chicago is such a vibe—full of culture, energy, and some of the best (and most affordable) eats in the city. If you’re a foodie like me, you’ll love exploring all the spots nearby. One place I highly recommend is Hing Kee. Their hand-pulled noodles and dumplings are on point—fresh, flavorful, and easy on the wallet. If you’re looking for a clean, convenient, and authentic Chicago experience, especially in Chinatown, John’s place is the move. I’d definitely stay here again.

I can't recommend this Airbnb enough! From the moment I walked in, I felt right at home. The place was not only extremely clean, but also beautifully decorated with a very welcoming atmosphere. The space is also very spacious, which was a huge plus. The host was incredible, super kind and helpful. There’s so many restaurant and fun bars in the area so there was always something to do on our down time. Thanks again Will for sharing your amazing space!

The location was great. The place was very clean and felt homey. I am very happy with the host and will stay again at their place next time I visit Chicago!

We enjoyed our stay at Yuyi’s. The space was very clean! There is a beautiful park across the street, delicious restaurants all around, and a grocery store 4 blocks away! We traveled in for business and it was perfect for us, Would love to stay again the next time we are in Chicago.

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!

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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

We had a great stay at Michelle’s “Heart of Evanston.” I loved the indoor garage parking option with easy in and out. If you have a large vehicle /SUV, maneuvering in and out of the spot may be challenging depending if the spot over is occupied. We have a mid-size SUV and had no issues. The room was easily accessed from the garage and we had no issues getting in. The place was clean and well organized. I loved that it smelled clean and also had a faint hint of bleach in the bathroom. It was a little warm in the bedrooms at night but we used the air conditioning to bring the temperature down. Town is very walkable and we enjoyed the local restaurants (Taco Diablo, Bat 17, Bennison’s bakery). We found the town to be very quiet - almost too quiet for what we expected but after our visit to Northwestern found out it was spring break for the students. Michelle was available for any questions and always replied promptly. We had a great stay and 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.