Family-friendly holiday rentals in South Side

Kyle's apartment was a visual feast, with fun and eclectic decor, furniture, and artwork! The listing states some quirks, which was accurate, but nothing that diminished the quality of our stay (for our family of 3). We didn't have a long enough stay to enjoy the full kitchen and dining table much, but would be a well-supplied kitchen for preparing full meals. The shower had some quirks but luckily Kyle even prepared a Youtube video to show and describe exactly how to turn on the shower. Part of the quirks of an older apartment building is radiator heating, which gives some 'clanking' and other annoying noises at times, so if you're noise-sensitive that's something to keep in mind. Kyle's local guidebook was helpful (unfortunately too long of waits at the places we had hoped to try) but found other options in the area for dinner. Our family of 3 had plenty of space for sleeping and lounging. This is a really cute space in a great location and a good close to downtown spot.

Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!

This home in Chicago was exactly as advertised. Perfect for a girl's weekend in Chicago. Plenty of space for sleeping, large bathrooms with plenty of mirrors to get ready. The house was well stocked with everything we needed for a perfect weekend. The location was great too. was able to walk to bars and restaurants or take short Uber anywhere we needed to go. Having off street parking made it even better for out of towners who drove to the destination. I would definitely book again when traveling with a large group.

Incredible hosts, incredible location and apartment. Would stay again anytime!

The location is really well suited for walking around the Logan Square neighborhood. The apartment was very clean and exactly as you see in photos. It’s right by a park too if you happen to have a dog. The hosts did a great job with communicating instructions (they also have the cutest pup). Overall I would highly recommend a stay here if you’re looking for a nice and traditional Chicago brownstone Airbnb.

This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.

Afsha’s place was a great base for our family trip to Chicago. The home is clean and well maintained. The off-street paring spot is a great bonus. Afsha is a great communicator and host. We hope to stay again on a future visit.

Tracy's home is clean, comfortable, and feels like a great home to return to when you are visiting Evanston. we didn't get a chance to cook in their fabulous kitchen, but I plan to next time!!

Great weekend for our 25th reunion. We were 8 adults. Enjoyed the spacious dining room. Kitchen was well stocked. We hope to spend our next reunion weekend back at the house!

I had an amazing stay at this place. Felt like home.The space was clean, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable visit. The host was incredibly welcoming and responsive, making sure every detail was perfect. The location was ideal, close to local attractions yet peaceful and quiet. It truly felt like a home away from home, and I can’t wait to book again for my next trip. Highly recommended!

We loved our stay here! The apartment is much more spacious than we were expecting and there was more than enough storage space for our luggage. We were disappointed a bit at the poor quality of the beds but appreciated the thoughtfulness of the noise machines to aid in good sleep in the middle of the city. We would absolutely stay here again!

Rose is a totally lovely and nice landlady. Very helpful. I felt super comfortable and taken care of during my stay with her and her family.

Perfect location, walkable to everything! Clean unit and spacious for my family of 6. The listing is accurate in saying that there is ‘city noise’ while sleeping, the host has a sound machine and ear plugs for light sleepers. Would stay here again!

The apartment was just what we are always looking for when traveling to Chicago. Garden apartments are great for old knees, just a few stairs and you are in or out. This apartment was spotless all the furniture was comfortable with plenty of storage space for a long stay, we were there a week. The kitchen has everything except a stove, not really something I use while on vacation, there was a toaster oven that would work in a pinch. The bathroom was spotless with a great shower, and "my favorite" a heated floor. I am a barefoot person at night and the heated floor was a welcome amenity. The neighborhood is great, safe, walkable, plenty to do in area and public transportation is close, short walks to the L or bus lines. Most important, Susan was a great host. She easy to get ahold of when we had questions, she checked up to make sure everything was okay. I hope we get to stay in Susan's apartment next time we visit the area, which is often.

This apartment in Skokie worked out great for 3 of us visiting family in the area. It was very convenient - short walk to 2 grocery stores and transit. The kitchen was well equipped with very nice appliances and plenty of dishes and pots & pans. Andy & Maral were very friendly and always very responsive.

We had a great stay! The pictures did not do the space justice, we loved it! And Charissa was so friendly and responsive, it really made our trip so easy

Convenient location with lots of space

This place was perfect for our quick trip to Chicago! The hosts were very helpful and friendly when checking in. They live just upstairs, but our place was still very private. I highly recommend staying here!

Fantastic place in an awesome location. Very walkable part of town and a great spot to easily get to Wrigley Field. Found a number of great bars and restaurants in walking distance during our stay. Would definitely stay here again!

We loved this stay and can't wait to return. It's a older, clean, well loved & maintained home, in a beautiful, quiet and safe neighborhood. We're moving and this was a test for the style of home, community and train system. We drove in, but used CTA all week. The walk to the train was an easy 15 minute's or 20. The walk to the main street just 10. We were out late most nights, St. Patrick's Day week, but never felt unsafe walking back at 1am or so. So many good restaurants, we couldn't try them all! Fun little pubs on the corners. A comedy club with free shows during the week, and the friendliest people. This was the best holiday/ scouting trip I could have hoped for. Now, I could write a novella about how wonderful Elizabeth is. I've traveled all over the world, in many rentals, and she is hands down the best in service I've experienced. From email updates to a full call about restaurants on our drive in, she exceeds anything we expected and we will be renting here again.

Felt safe in the area . Easy parking . Close to CTA train and one stop away from our destination. Clean and quiet home felt like home also . I highly recommend this place if you attending any event at the united center and want to visit cloud gate easy directions. Joyce thanks for the wonderful stay .