Kid-friendly vacation rentals in South Side

This home far exceeded all expectations! Every inch of the space was thoughtfully designed and beautifully curated, making it feel both luxurious and welcoming. The decor was stunning, and it was clear that a lot of care went into creating a perfect environment for guests. The kitchen was fully stocked with everything you could possibly need, and the bathrooms were equally well-equipped with all the essentials. Every detail was considered, making the stay seamless and stress-free. The hosts were outstanding—responsive, accommodating, and incredibly helpful throughout the stay. I couldn't recommend this home more highly for anyone looking for a truly exceptional experience in Chicago!

It was amazing with the kids they enjoyed the mini golf a lot ….spacious bedrooms very good kitchen and cleaned washrooms …overall it was great

We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.

We stayed for two nights and really enjoyed it! The place was beautifully decorated, super clean, and had everything we needed—including coffee. It’s close to the city, which made getting around easy. The neighborhood wasn’t the nicest, but the house itself felt safe and had two parking spots. Lots of beds too, which was great. And the host, Jesus, was really nice, friendly, and had great communication. Would definitely recommend!

We had a great stay at this place. The location is very nice. Get to be outside of downtown still while close enough to visit whenever you’d like. The retro vibes of the home itself is very cozy and unique. Will definitely book again if we ever come back.

I loved the little cottage. Quiet neighborhood, felt safe. Restaurants were walkable. Reached out to Marilyn for a breakfast recommendation and checked out bacon and jam, amazing. House was easy to find. Clear instructions. Felt at home.

Lovely home, very clean, even bigger than what it looks like in the photos, nice and responsive hosts

Great place. Great communication. Perfect for what we needed. Great house. Great neighborhood, right outside of downtown.

This home was such a beautiful historic property. The kitchen was beautiful and it was in walking distance of Barack Obama’s Chicago home. That was such a beautiful street to walk and enjoy the homes. The bus stop was right out front and transportation was easy using the busses and metro. Thank you for the use of your beautiful home.

Gogo’s place was great. He was super helpful and the location was perfect for our trip!

Absolutely loved the stay I didn’t not realize this space was spacious but still quite cozy and very well equipped for just about anyone coming to Chicago to visit. Very clean loved that it’s hassle free to park and no stairs is always a win in my book. Love the artwork and the games available I didn’t spend too much time inside but I enjoyed the time I did spend and I’m definitely recommending this location and will be back again once I discover a few other side of Chicago I think this is by far my best stay since using Airbnb

Spacious and clean place in the quiet, convenient and safe area! The host is very friendly and response quickly when you have any questions!

Hena was super attentive and reached out to check in a few times during our trip. The apartment was clean and comfortable and a great place from which to explore Pilsen or hop on bikes and head up into the busier parts of the city. Thanks for a great trip!

Very convenient/walkable to green and red metro lines, as well as a few blocks from a great grocery store. Felt safe on a quiet street yet still very close and accessible to key Chicago locations. I was in town for a graduate class on the south side and this was a great home base.

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.

I would definitely stay here again. Plenty of space, felt safe, nice accommodations and very clean apartment. Whenever I messaged Sherry for anything she responded right away and even went above what I asked for.

Everything was great! The location was perfect—close to most of the attractions we visited during our stay. We really appreciated how well everything was set up. The honey was a lovely touch, and we especially enjoyed the peaceful, quiet atmosphere away from the city. Thank you for a wonderful experience!

A wonderful getaway place to go to for couples. The jacuzzi tub was amazingly relaxing and the location was peacefully quiet. My boyfriend and I absolutely loved this place and will be coming back soon!!

The location was great. About 15 min from downtown. The place was beautiful and clean. I would definitely book with Julia again.

My daughter and I stayed at Izakaya Studio on a recent visit to Chicago. The studio is great and Brett made it so easy to locate everything we needed to make our stay enjoyable. The next time we stay I hope to spend more time exploring the neighborhood because there were so many restaurants and shops to choose from (lots of open-air patios and decks which would be so nice during the summer season). The walk to the blue line El stop felt safe and quick. We loved the studio's layout. The kitchen and bedroom areas were separate and Brett has two big, comfy chairs for relaxing, and ample island space for eating or using as a work space. My daughter had some virtual work meetings and the Wi-Fi was reliable. The kitchen was well stocked with everything you'd need for meal prep. We ate out each day, but our delicious breakfast take-out came from a place right up the street called Yolk. I highly recommend the Izakaya Studio for a relaxing and fun visit to Chicago.

Milan runs a professional Airbnb service and promptly responded to all our queries. We stayed at Apartment No. 605 which, was clean and had all the required amenities for a comfortable stay.

In town for work and this was perfect place to stay for team. Easy walk to the shops and restaurants in Fulton Market while still providing a peacefully quiet setting. Bright, open and clean apartment with 3 large bedrooms. Nice kitchen for all meal-preparing needs If you don’t want to cook, no problem. Some of Chicago’s best restaurants are just a short walk or quick uber ride.

The home was perfect for a quick business trip. It was clean and as described. Anne was a great host and easy to communicate with!

The time spent here was wonderful. This place has everything you need to feel at home away from home. Everything was clean and comfortable. The area was also really nice with tons of food and drinks within walking distance. The blue line is a short walk away and the busses run on the corner. I would definitely stay here again when coming back to Chicago.