Family-friendly holiday rentals in Grant Park, Chicago

We had a great stay in Logan Square. The location has walkable access to the Blue Line making downtown easy. While this is a lower level unit, this does not feel at all like your standard “garden level”. It was full of windows and bright. Furniture was very comfortable. Bathrooms well appointed with amazing shower pressure. The bedroom is so quiet you get a great nights sleep. Bonus points for lamps on BOTH sides of the bed. The closet had high quality hangers plus good storage. The kitchen has everything needed for cooking or for storing leftovers from fabulous restaurants in area. The garage is a great bonus. Our young adult children live in the area and it was prefect for them to come over, hang out and visit with us. We spent time outside in the garden area with the fire table. Bryan was very responsive and helpful through our four-night stay. We will be back!

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

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.

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.

The place was as expected, and had everything we needed. Location is great, close to subway and many restaurants. Elizabeth is extremely responsive, and gave us a heads up regarding some road work (which didn't affect us in any meaningful fashion). Great host, great place.

I would highly recommend Dennis' place. It was super clean. Had all the amenities you may want. Close to a lot of places yet quiet. We felt totally safe and loved the balcony.

We loved our stay at Kyle’s place - it was decorated SO cute (I went with two girlfriends and I’m pretty sure we all squealed with joy when we first opened the door). The location was perfect - just a quick walk to all the shops and restaurants Logan Square had to offer - and to public transportation (which we used the whole time in Chicago). The neighborhood was very peaceful and quiet; we all felt very safe. When I come back to Chicago, I will absolutely be staying here again. Thanks for sharing your space with us, Kyle! We loved it! (Side note: you gave me so many ideas for house decor, your style is impeccable!)

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 was a really amazing host! She was friendly, helpful, caring and went over and beyond to make sure me and my kids were comfortable and had everything we need. Gave us lots of great recommendations to restaurants and as a first timer in Chicago she made sure I was aware of the traffic and other helpful information! My kids LOVE her she was vey nice, patient and gentle with them. Kid friendly house/area VERY quiet. The beds are the BEST after a long day of traveling very comfortable. The place was beautiful very nice decor and nicely maintained. We will definitely be staying here on our next visit to Chicago.

Comfortable, homey place for our group of five. Great back deck for outdoor time. Wonderful neighborhood with lots of shops and restaurants. Good beds.

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

Great host. Would definitely stay again. Good location, convenient subway within a few minutes walking. 12 min to Downtown.

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!

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.

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.