
Kid-friendly vacation rentals in South Side
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in South Side
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
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Popular amenities for South Side kid-friendly rentals
Kid-friendly house rentals

Game Room | Fire Pit | Full Gym
Great family friendly location. Kids loved the game room. Clean and comfortable with a responsive host.

Comfy Home w Access to Major Roads/Hwys, Huge Yard
Great place to Spend the night or even a week. Our fight to Miami got canceled and his place was the perfect place for our family of 5 to spend the night. Friendly and responsive would definitely recommend to anyone looking for a place to stay in Chicago.

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
Lovely place in a good location.

Family home on fescue
We loved it and we come to Aurora a few times a year. We will definitely be staying again.

Bliss in Brookfield- 5BR, 3BA
Nice to have a spacious place to stay with family. Our toddlers were in heaven in the basement toy/family room. Bedrooms and closets were spacious as well. Communication with host was easy with prompt responses. We would stay at this property again.

The Blue House: Family Retreat
Clean and kid friendly! Just as described. Perfect place to hang our Easter vacation with our group of 13!! Everyone felt comfortable and accommodated. Only thing I’d change if I could, more pillows! We’re a pillow loving family. Otherwise everything was great!!

Evergreen Retreat
This is a very beautiful house with TONS of space, big and perfect for my healing retreat, I hosted 9 ladies, the backyard is huge plus there was an outdoor event area. The place looked exactly like pictures, clean, host was responsive and polite. The house is very relaxing and peaceful. I would definitely recommend!

Rivera House-fun and comfort steps from the beach
We had an absolutely lovely time! We took a family trip and the house was perfect for 6 adults and 5 kids. The beach was super close to walk to. The large house was perfect for everyone to have their own space. The spacious living room/kitchen was a great place to spend family time cooking, playing games, eating, etc where we could all be together but doing separate things. There were plenty of towels for everyone for that many days which surprised me! Inga had thought of everything! There was all the extras you might need too like cooking basics, sunscreen, flashlight, bug spray, beach chairs, toys, umbrellas! And the espresso machine was also a hit with our family! Thank you so much Inga for having us!! We made memories that will last a lifetime in your beautiful home!
Kid-friendly apartment rentals

The Biddle House (#1)
We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!

Flexible Apt. for 8 by Oak Park-CHI
Lois is a great host! The accommodations were perfect for what we needed. Her space was clean and essentially everything you need from your airbnb. I will mention the beds are very uncomfortable:/ but that's the only thing I could complain about! thanks for having us :]

Cozy Garden-Subterranean Apartment
Jenny went above and beyond! She was super communicative & very friendly. She even let me check in before checkin time, which I greatly appreciated. The apartment has literally everything you need. All the little details and small things you could want, are there. I would highly recommend staying here for a longer extent of time, as you would feel as if you’re in your own home.

Archways at the Lincoln Park Zoo 2bed/2ba
I had an amazing time staying at this adorable Airbnb in Lincoln Park! The space was just as cute and cozy as the photos, and everything was super clean and well-maintained. Jessica was incredibly welcoming and responsive, which made the whole experience even better. The location was perfect—tucked into a charming neighborhood but still super convenient for exploring the city. I was able to catch a Cubs game at Wrigley Field and stroll through Millennium Park to see the Cloud Gate (the Bean), all without any hassle. I’d absolutely stay here again next time I’m in Chicago. Highly recommend!

*The Belltower Haven*Large*Family Friendly*Wi-Fi
Great spot to stay and James was awesome, would highly recommend this place to any of my friends, thanks again!

Adorable 1BR apartment near Northwestern
Nice place to stay in a good neighborhood! Would stay here again, thank you!

Bright, Cheery Logan Square Getaway
Great location! The place was very easy to find and within walking distance some really good restaurants. Loved our stay!

2nd floor of 1908 brick two-flat in Logan Square
Thank you for sharing your wonderful space. It was perfect to spend time as a family while moving our daughter in Logan Square. The park nearby was so easy to manage for our dog who joined us. Paul was responsive and helpful. Got to meet his pup who was adorable. Will definitely stay here again
Kid-friendly condo rentals

Entire 3Bed/2Bath Condo Near McCormick & Metro
We enjoyed our stay. John works hard to offer the best experience to his guests. The place was super clean and welcoming. Photos are matching. Close to everything with UBER. Some restaurants are located in the block. I recommend this appartement.

Convenient & Spacious 3BR Condo w/Free Parking
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend

Dream Condo steps from Wrigley Field!
I would definitely stay here again! Walking distance from Wrigleyville bars, restaurants and stadium. Comfortable, clean and quiet.

Luxurious River North 3BR/2BA- Free Onsite Parking
Neel went above and beyond for my family and I during our stay. The unit was quiet, fun to hang out in, extremely clean, great layout for a family, very convenient parking, and quiet. I would highly recommend staying here! Thank you Neel!

1 #33 - 4 Bdrm Condo - McCormick Place, Chinatown
Very great for a large group.

Gamers Getaway 20 minutes from downtown
Loved The Space! Everything Was Perfect! Any Problems Or Any Questions Daniel Was Very Helpful! THANK YOU DANIEL

Lovely 3-bedroom condo, free parking, Unite 1
This place was awesome. Felt very homie and comfortable. I love the decor and that there was a TV in each room. This place was beautiful and i wouldn’t mind staying again.

Lincoln Park 2bed/2bath in Historic Neighborhood
This was our favorite spot in Chicago thus far! The location was amazing, so close to everything! My 7 y/o is obsessed with the Sears Tower and was thrilled we could see it from our window! :) The place was clean and beds were super comfy. Would totally stay there again! Thank you, Michael!
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- Museum of Science and Industry
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Chicago History Museum
- The Field Museum
- Wicker Park
- Flossmoor Golf Club
- Willis Tower
- Brookfield Zoo
- Skokie Country Club
- Chicago Cultural Center
- Lincoln Park
- Garfield Park Conservatory
- Promontory Point
- Washington Park Zoo