Bed and breakfast vacation rentals in South Side

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.

Great location, great accomodations, and most importantly amazing hosts! Tripp and Todd were so welcoming, I felt right at home. They provided helpful suggestions for meals, activities, transport, etc. Hosts were in communication from the moment I landed to coordinate checkin, and allowed me to drop off my bags early when I arrived prior to the check in time. The location is great, only a few minutes walk to Clark Street which is well populated and has many restaurants and independent shops. Do yourself a favor and book with Tripp and Todd if you ever find yourself in Andersonville/Edgewater!

This country house is well located, quiet, off the beaten path, but easy to reach. The rooms are super clean and well appointed. The Hosts are very social and take great care and interest in their guests. They are great communicators, and appreciate all feedback. Best advice to potential guests....must like dogs and good conversation,( and movies). And coordinate plans closely with hosts to take advantage of their local tips and advice. and Respect for house rules will make for a smooth stay for everyone. Travelers can not go wrong choosing to stay with Laura and Mike, they were/are the best.

We felt warmly welcomed to Patricia’s home from the moment we arrived. The bedroom and bathroom were comfortable and the breakfast was amazing! A special breakfast was even prepared to accommodate a food allergy! Lovely visit at breakfast on the outdoor deck, we would stay at Patricia’s again!!

Everything was perfect! Enjoyed the room and breakfast. Staff was very friendly and helpful.

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!

Caryl was a wonderful host who went above and beyond to make sure I was comfortable. My room had everything I needed, and the house is a convenient walk to UChicago. I will definitely be staying here again on future visits!

A lovely room, clean and cozy, in a great location. Very walkable! My room was first floor street-facing and I didn’t notice any outdoor noise (expect a little rumble from the train). Laura was incredibly responsive and helpful. I’d stay here again. I didn’t want to pay for parking, and I’m familiar with the neighborhood, so I chose to park several blocks away.

It was a wonderful stay with a very hospitable host. We loved the access to the beautiful kitchen with instant hot water for tea. The homemade baked goods were a delicious treat in the morning. The room was immaculate. The back rooms face the tracks for the busy Chicago Transit Blue Line, so if noise bothers you, ask for a room facing the street.

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

Loved the king sized bed, and the large shower. Location was perfect. We stayed in the Wolcott which is on the front ground floor. Has a beautiful brick fireplace in front of the bed. I think this building had about 6 units. Everyone was friendly. They provided a community kitchen and breakfast was nice. Bagels, muffins, pastry, boiled eggs, oatmeal, coffee &tea, and juice was all very fresh. Easy in, easy out! We’ll return soon! Thanks!!

Nice chill spot

Great on all fronts. Lovely hosts, exceptionally clean room, great food, can't say enough positive things. Looking forward to staying here again sometime.

She was very polite and helpful. She didn’t mind letting us back in late at night. I would definitely stay here again

Nice and cozy bed & breakfast in a great part of Chicago. highly recommend

I was in Chicago for the night, and this stay made me feel right at home! We had a BEAUTIFUL room, and all the shared spaces were spotless and well-designed. I will definitely come back to Chicago and book this unit again. Most comfortable mattress I've ever slept on as well.