Apartment holiday rentals in South Side

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.

First off, the pictures don’t do this place justice! It was such a beautiful and spacious unit. Everything was very clean, the host was great at communicating & making sure we had everything we needed. It was a cute community that felt like home. The drive to downtown was so quick and smooth. Close to anything you might need. Definitely recommend this place and will look for it next time we come to Chicago!

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!

Great experience and a flexible, highly communicative host. Would stay again in a heartbeat!

The place was beautiful and exceptionally clean. We loved the decor and all the thoughtful details throughout the house. We specifically chose Ademola’s home for its proximity to downtown Chicago and the excellent reviews—and it did not disappoint. Although we initially had trouble finding parking, Ademola’s husband kindly came by and provided parking permits, which resolved the issue for the rest of our stay. The customer service was outstanding—any questions we had were answered within 10 minutes. We had a wonderful time and will definitely be returning. Thank you for your hospitality!

Aminah's place was amazing. We were here for a conference and had to fit many of us in the house, and we fit great. Beautiful home, extremely clean, and very responsive. Overall it was a great stay!

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 stay in a lot of Airbnbs. At least 3 a year, most of them in Lakeview. This was the best one! I’m originally from Lakeview and have been disappointed how commercialized and impersonal Airbnb has become. This was the opposite of that. It was so homey, I felt like I’d lived there my whole life. Would definitely stay again.

Loved this condo. We had 7 adults staying and felt comfortable. Having a dedicated parking space was super helpful and on street parking was easy. Please note this is a 3rd floor walk up so if stairs are a problem you need to consider if this works for you. Easy access to Midway airport and Chinatown were also great features.

Had a wonderful stay and place was clean with two nice bedrooms. Location was convenient with brown line an easy walk. We were able to get to Wrigley quite easily and downtown. Would definitely stay here again!

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!

What a great find! I'm talking about the room AND the host! The beds were very comfortable and the amenities were all we needed. The artwork was wonderful and the design of the rooms (lamps, table, chairs etc) were great. I especially loved the small room heater, it looked like a mini fireplace, I want one for my room at home! Kaye has thought out what a guest needs with all kinds of extras (covers for the chairs for pets), extra blankets, packet full of local information, and clear instructions. She was responsive when I had questions or needs. I was glad to meet her as well, easy to talk with and a very interesting person who knows Chicago extremely well. If I make it back this way, I would definitely stay here again.

I had a great stay! The Airbnb was easy to get to and in a fantastic location within walking distance to restaurants, bars, gyms, and public transportation. The space was very clean and well-maintained. Would definitely recommend and stay here again!

Cindy was a lovely and responsive host and the apartment was great. She was very responsive and let me adjust the booking without any hassle. There was plenty of towels and blankets, and the coffee area was well stocked. Location was in a great area of lincoln park very close to the zoo & actual park area and not a far walk to the cta/many bus stops. Would definitely 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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

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.