Family-friendly holiday rentals in South Side

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.

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!

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!

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.

The excellent host explained everything in advance, agreed on all the nuances. We had a great time with a group of 12 people. In my experience, I recommend it.

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.

We enjoyed our stay at Michelle's place! We were visiting our son who recently moved to Chicago, and it was just a few blocks away from his apartment. The Ukranian Village neighborhood in Chicago is very cool....neat architecture, very walkable, etc. We went to the Field Museum and also went to a Cubs game while we were there. Her place was just as described, very clean, and Michelle left many extras (snacks, filtered water, etc.) for us! Would recommend her 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.

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.

Good location. Condo was very clean with comfy beds. There are 3 flights of stairs to get to condo- no problem for us but be aware

⭐️⭐️⭐️⭐️⭐️ 5/5 We had a wonderful stay! The space was clean, cozy, and exactly as described in the listing. The host was super responsive and made check-in seamless. We especially appreciated the little touches and great local recommendations. The neighborhood felt safe and was close to everything we needed. Would absolutely stay here again and recommend it to anyone visiting the area!

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.

Great building, super fun neighborhood easy to walk to everything. Great spot to be out late at night. Definitely worth booking.

Really enjoyed our stay! We found it easy to get everywhere we wanted. If you get a chance check out Move Along Coffee a few blocks away.

Loved our stay. Right in the middle of everything we wanted to do in Chicago. If we couldn't walk to it, public transportation was readily available. Stephanie was always friendly and responsive. Would definitely stay here again.

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.

This apartment had everything that I needed during my work-and-play trip to Chicago. Easy access to public transportation, pleasant walks to the river and the west loop, and the gym and pool were awesome. Stephanie was extremely quick to respond and friendly from start to finish. I would be very comfortable staying here again next time I’m in Chicago.

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.

Run, don't walk, to book this location for your Chicago stay. The view of the Chicago skyline is perfect, even better than if you stayed in Downtown itself, sometimes all you see is the wall of another building and no view. The instructions how to get there are very clear, if you're a little intimidated like I was about going to a big city never fear. The instructions are clear, easy to follow, and transit is close by to take you wherever you want to go. Overall great trip, thank you!

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

We knew from the photos on the listing that the view was spectacular and that the apartment was nice. We were not prepared for all of the extra, thoughtful touches that were part of this property. It was like staying in a spa! The lavender oil infused warm washcloths, towel warmer, and bathrobes were unexpected and much appreciated! Thank you, Amanda, for having us at your property. We'll be back.

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.