Holiday rentals with breakfast in South Side

We stayed at Rachell and Cyd’s for about 3 months after relocating to the area. We absolutely loved the home as well as the walkable neighborhood, park, and downtown. We were made to feel at home with tons of useful items, abundant clean linens, and a cozy space. Cyd was very responsive at all times. This lovely house is a no-brainer for a comfortable stay on the North Shore. We will miss our time here.

FANTASTIC!! Great host! Awesome location! Clean house with everything needed available.. my kids loved the house, it felt like home away from home. Peaceful … Wish I could give more stars than 5!!!

Dawn is definitely a Super Host her airbnb is exactly like the title, Classic Charm with Modern Flair, guests will not be disappointed , from the time you walk through the door until checkout, you'l feel you're in a 5-star hotel, but at home, it was roomy the beds(queen sized) in every room with hotel style linen amenities such as appliances which included washer and dryer and hair dryer, a sun room with games for children and family, TVs in every room except dining and fully equipped kitchen quality dining ware, I'm sure this summer will be booked full because there will be a great outdoor area to enjoy, bottom line I hope next time I visit my Chicago family, she will have availability, Dawn, Thank you !

My family and I rented Kevin's place for my niece's wedding. we enjoyed ourselves and the accommodations. Kevin was super responsive and made us feel welcome. the neighborhood is isolated but peaceful.

Beautiful home that was perfect for our families!

Perfect place to stay for our visit to Chicago with friends! There was ample room in the BnB for all of us, including a spacious dining and living room. The kitchen was very well stocked including coffee, juice, eggs, and toast for us to make our own breakfast (a welcome surprise!). It was very walkable to transit, with a CTA Blue Line station nearby. Thatheu was very responsive and check in was straightforward. Also the later check-out time was very convenient as we were able to take the time for breakfast before heading out for the day. Thanks again for helping us to have a great trip!

The house was great for what we needed. Small house in a very quiet and neat neighborhood. Thanks for allowing us to stay.

We had a wonderful stay at this property, it truly felt like a home away from home. The entire place was exceptionally clean, and the kitchen and dining area were spacious and easy to move around in. Both bedrooms were spotless, and the mattresses were incredibly comfortable. If you’re looking for a quiet, private place to stay, this is the perfect choice. I would definitely stay here again! 😊

Perfect spot for 2, more spacious than expected for a 3rd floor apt. Easy, clear instructions when viewing the listing and inside the apt

Well equipped and clean Instructions are very clear

DW was very flexible and responsive. He was very accommodating to allow us to check in early and flexibility on check out as well. The location is good - if you are super sensitive to the noise of the train it may not be ideal, but the proximity to the train stop and Wicker Park was great. You must go to Mindy’s bakery - if I lived this close to a place like that I would gain so much weight 😅. Thanks again!

As most everyone says, this is a spacious and very comfortable, generous place. There isn't a welcome binder with house instructions, restaurant menus, maps, etc., so we sort of winged it, but Howard was available for questions. The dog(s?) were a little barkier than I'd expected, but not a deal-killer. The apartment is very clean and cheerful, with lots of good light and comfy seating. Recommended!

We had an amazing stay and our hosts went above and beyond to make our stay great. I reached out for recommendation to host my mom’s memorial service and they not only helped me find a caterer (who was amazing!) but also gave recommendations to hold her event. Upon arrival, they left some amazing popcorn for us and we all felt right at home. We had an amazing stay and I would definitely stay here again. Thank you so much for hosting us!!

One of the best Airbnb's we have stayed in. The location is great with excellent bars and restaurants nearby, but in a quiet street. The accommodation is as advertised, but also includes everything you need for cooking and generally relaxing. I wouldn't hesitate to recommend this place and if we come to Chicago again I would definitely try and stay here

Great location nice view amazing host

Our stay at Megan's place was awesome! Very cute apartment in a great neighborhood with all the amenities you could ask for! Megan was a great host! Will definitely stay here again when visiting Chicago!❤️

Communication with Caryl was so easy and I was very appreciative when she was able to juggle a few things around to accommodate my son's stay. My son said the house was very easy to find, beautiful, and in a great location. He said he was able to walk to campus, places to eat, and wherever he needed to go. The backyard was very relaxing and his room and bathroom was very big and comfortable. He said he would definitely stay there again when in Chicago. Thank you again Caryl!

You get exactly what you look for. The location is awesome and I found parking immediately. Great place

I unfortunately had to cancel at the last minute - but Christianne and Patrick were still so incredibly thoughtful. They sent me the weather forecast in advance as a heads up for packing, and even some encouragement for getting through an emergency situation at home (despite the fact that I was doing them a total disservice with a last minute cancellation). I would look to stay with them again in the future as priority #1 if in Chicago! They clearly understand what it means to go above and beyond on the hospitality front!!

Very cozy place in a calm tucked away neighborhood. Would definitely stay again!

Mary's place was a great location for our short trip to Chicago! It was a short Uber drive from the airport, and a short drive to the All-State Arena. We did arrive late at night due to flight delays and opted for an Uber versus the train. I am glad we did cause it seems like the train station is under construction for the side we needed and would have been a bit more of a walk departing from the other side, but definitely not a dealbreaker or anything. The house is a short walk from this breakfast place that we actually went to twice during our short stay, with other options nearby. Overall, the house felt cozy and clean, but we did struggle with getting in the bathroom first thing in the morning with the other guests in the house during our stay. Mary was very responsive and a great host to us during our stay. The bed was comfortable as well and the room had amble space for a large suitcase, a carry-on, and two large bags with space to spare for two people.

Nice chill spot

Patricia offered us unparalleled hospitality with a unique balance between privacy and availability, with tasty and varied breakfasts. Friendliness and kindness did the rest making our stay extremely pleasant.

We enjoyed our stay! It was great to be able to walk to the University and restaurants. Our windows looked out on trees and backyard, which made for an extra peaceful stay in the middle of the city.