Family-friendly holiday rentals in Cook County

Our stay was fantastic! The house was gorgeous and clean and the view of the water was so nice. The beds were super comfy and the area where the property sat was peaceful. We had some issues with the internet going in and out while trying to watch a movie together, but we just turned the tv off and everyone went to bed. It's definitely a great location for any type of retreat or girl's trip. Thanks so much for a great vacation!

Great stay! Thanks for making it so easy. Big space for lots of family to be together and have space.

Everything was good just washing machine was not working and dish washer wasn’t operating good and there was enough toiletries

This was a lovely cottage and a great getaway from a busy Chicago life. We only spent a couple nights but we brought my dog and we just wanted to chill for a bit. Soaking in the hot tub was a must! The backyard was completely fenced in so my dog could roam and investigate while we enjoyed the hot tub under strings of yard lights, creating a peaceful vibe. Loved it! We cooked a lot (inside) since the weather was cool and windy and the well-stocked kitchen was much appreciated. Great coffee machine (bring your own coffee!) and dishwasher. They came in very handy. Comfortable beds, clean linens, adjustable thermostat with easy instructions, extra blankets and pillows... all you'll need to feel at home. Thank you for a great time and we can't wait to come back. Next time we're bringing our friends!

This is a wonderful spot. The place was totally immaculate, Bryan was very responsive and accommodated us arriving early. The place has everything you could want/need. We would definitely stay again!

i loved this airbnb, great spot if you just want to explore chicago. max was super quick with responses and helpful with any questions i had.

Great house with lots amenities. Hilary was very responsive and accommodating.

We had a great stay at Delphine's place in Uptown. The location is excellent, being on a tree-lined street, but very close to the Red Line, the Broadway bus, Andersonville, Little Asia, grocery stores and more. As we had a little kid, being right on top of the little park downstairs was also very convenient. On the flipside, it can get noisy in the summer with lots of kids/playgroups coming there, but as parents, we didn't mind. Delphine herself was very quick to respond via Whatsapp to all our queries before and during our stay. One thing to keep in mind at her place is that you are very much living in their home. If you are looking for an apartment that is only intended for guests, this is not it. While it is plenty big as a 2BR/2BA, it is full of stuff, furniture, photos, books, toys, etc. They have made a very nice office space in the main living area, but the drawback is that the living area is now very cramped. The main bedroom has 2 queen size beds in it, which is a bit weird, so we just ended up using one bed to keep our clothes on. The other bedroom with bunk beds is excellent for kids and more spacious. So overall, a great place and a great stay, and especially good if you are a couple with 1 or 2 kids. Just a bit cramped and crowded with stuff. We stayed for 2 weeks.

Had an amazing stay. Would definitely recommend. Very cool and unique spot.

Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

Jamie's place was absolutely adorable—just as pictured and described. The bedrooms were very nice, and the beds were super cozy. The kitchen was fully stocked with all the gadgets you’d need to prepare whatever you'd like, plus a few condiments, which was a nice touch. The bathroom was tidy and well-kept, with fresh, clean towels and linens provided. Jamie was more than welcoming and very accommodating to any requests. Even though she lives below the rental, she was incredibly respectful of our space—warm, friendly, and never intrusive. It truly felt like having my own little apartment. Overall, a wonderful place to stay, and I will definitely be returning.

Place was just as described. Easy instructions to enter and house manual was clear. Steve checked in to ensure all was well upon arrival

Lovely flat, excellent collection of games and books. Very well stocked, super clean. Hosts were very friendly and responsive.

Keith’s place in Bucktown is a great find. The place itself is just as described- a spacious lower level apartment with a separate sitting area and well-stocked kitchen. The location is in a very walkable area among beautiful townhouses and plenty of restaurants, coffee shops and bars. Conveniently located to public transit to get to downtown and the airport. Would definitely stay here again!

Lovely town house. Very comfortable and inviting. This was the perfect location. We parked our car for the duration and could walk almost everywhere. Excellent host who provided good info in a very timely manner. Very happy this was the place we chose.

We truly enjoyed our stay. It provided a great stop on our cross-country road trip and was a short walk to Northwestern University.

Great location in downtown Chicago with easy access to the city.

The location is perfect for getting to any part of Chicago. It's within walking distance of endless activities, and within one to two blocks of multiple "L" and subway lines that will take you anywhere. You are staying in the middle of the city, so you will hear the train and sirens throughout the night; however, the host provides disposable ear plugs which were very helpful. I had no problem sleeping throughout the night. Front desk staff is always friendly. The host is very responsive, and courteous. Washer and dryer in unit helped me with not having to pack as many cloths for my trip. Everything was spotless upon arrival. Would absolutely stay here again.

A great stay right near a Main Street. Tons of options for going out but still quiet in your space. Warning. You will smell the BBQ restaurant and you will salivating.

Second stay. Rose accomplishes blending comfortable clean accommodations with a relaxed and folksy vibe. Recommended!

Great location and nice floor plan. A bit noisy because of the elevated train, however, earplugs were provided and I enjoyed watching the trains. I would definitely stay there again.