Kid-friendly holiday rentals in Chicago Loop

Had a nice time, was flexible about parking spots.

Abby is a wonderful host! She is very respectful and is there if you ever need anything! The place was nice and clean. I would not hesitate to return again.

Musa was very friendly and helpful the entire time we stayed at his place. The house is big, neat and located in a nice and calm neighbourhood, ideal if you want to rest after a day in downtown. Good shops nearby so I recommend go for a walk around the beautiful Evanston.

Was a very nice and relaxing place to stay after spending time in the city! Really close to multiple bus stops which made the public transport really easy to access. The inside was very clean and nice, the bed is extremely comfortable! Would stay again!

It couldn't be better. No, it is not a luxury accommodation. It is the classic Airbnb, namely a room in a privately used apartment. Diana lives and works there alone. Above all, out of interest in foreign cultures, she rents a room with an opposite bathroom, which only the guests use. The accommodation is located in the Ukraine district, which is very quiet and about 30 minutes outside the downtown. In the morning, Diana surprised us with a prepared coffee machine (just turn it on), a few cookies and a lovingly prepared fruit plate. Bus no. 66 takes you quickly to the city center. We really enjoyed our time in Chicago. We received a lot of information from Diana, but also had very personal conversations. When we come back to Chicago, we'll check in with Diana! Thank you for the authentic and so lovely stay!!!

Tippi was a great host! The room was clean & comfortable. The area has a few gems and great transport options. Would definitely recommend to others to stay if you're looking for a place not too far out of the city!

Ryan was a great host. He gave very clear instructions which made checking in very simple. The location of Ryan’s place was perfect for my half marathon and conveniently located near the L so I could get to anywhere I needed to go. The house was very quiet even with it being fully booked. My room was spacious and very comfortable.

This was my first Air Bnb stay & it was 1000% worth it. I stayed at the Marriott OHare for two nights then came here for another two nights and I felt more comfortable, slept better and more at home here. I was able to walk peacefully back after a day in the city with no issues. I was a bit skeptical about the shared space but it was if no one else was really there and the one person I saw was so pleasant and respectful. I would definitely be back here! It felt like my home away from home.

Dean was the best host my girlfriend and I have had! He is proactive, friendly, great with communication, and provides everything you need for a great stay. Not only this, but the place was extremely comforting and beautiful! We had an amazing stay and would love to stay here again! Not to mention this place is an amazing price for how nice the stay was! Thank you Dean! You rock😎

We watched together with my wife “Frida” is story and house is vibe matching I had an incredible stay at this gorgeous Mexican-style house! The home was beautifully decorated with vibrant colors, traditional touches, and an authentic charm that made the experience truly special. Everything was spotless, the amenities were perfect, and the attention to detail was exceptional. Janet was welcoming and responsive, ensuring a smooth and comfortable stay. The location was also great, making it easy to explore the area. I highly recommend this place to anyone looking for a unique and memorable stay—I can’t wait to come back! It’s in my wishlist Janet thank you soon come back to visit Chicago in a week

We loved our stay in the Pink House, which felt truly like a home away from home with everything we could possibly need. You can tell how thoughtful Niki and Sean are about their space and that they care about their guests having a lovely time - especially appreciated the comfy linens and snacks! Perfect location too with an easy walk to the L and plenty to discover just by wandering around the immediate neighborhood. Niki has all the recs.

I loved this stay! It was in a great walkable area and not far from downtown Chicago. I would definitely stay again.

Very clean, large, open plan apartment in prime location, right at Chicago south loop. Close to many sites, even Trader Joe's is near by. The elevated railway may cause some vibration and noise but soon will get use to it.

Next to the trains, a apartment with separate bedroom, living room, kitchen and bathroom, even a laundry room available if necessary and a host who responds quickly and does not hesitate to give advice on Chicago. I highly recommend!

This is the place! It’s even better than pictured. It’s spacious and super clean. In the heart of the city, you’ll find a safe neighborhood, walking distance to everything and a spectacular view. Check in is a breeze. A security guard as well as a key-fab for elevator access added to our sense of safety. Our host responded immediately. This cool flat is also very quiet. I didn’t want to leave. I would have extended a week. Grab this one if you can. Mom and I will be back for sure! We loved our stay.

Really enjoyed the spaciousness Carmen’s place offered my brother and I. The living room was my fave with its open concept. Just be vigilant at night and you’ll be fine. Don’t hesitate to book!

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.

Very clean and spacious airbnb - Adam was super easy to communicate with and checked in to make sure we had everything we needed. Thanks again!

Great stay at Anne’s place. She was very communicative and went out of her way to ensure we were comfortable. We would definitely recommend to anyone coming to the Chicago area!

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.

I had an amazing stay! Place was very accurate to the post on Airbnb and the host was very polite with clear instructions, and check in! Thank you for providing such an amazing Chicago experience for me and my husband!

Great host and great stay! Beautiful home. Thank you so much!

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.