Bed and breakfast vacation rentals in North Side

The hosts were great, and the property is beautiful! Our room was very clean and felt very private.

Edward and Ellen were amazing hosts. Edward was up till 12 to let us in(really unusual, but really great). He showed us the entire area even at that time, and made sure we settled in well. The refrigerator was full of great stuff, all for the guests, which was impressive. And great selection of coffee. ;) Overall, I would recommend this place to anyone.

We had a great time staying here. Christiane and her husband are both very gracious hosts - they had breakfast available for us every morning & made us feel right at home.

Very neat place with several bedrooms. Host was clear with directions for how to check in/get into apartment and a very simple check out. No surprises everything was exactly as the host described. No chance at parking on the street but not the host fault.. plenty of nearby parking garages, just gotta pay for them. Wish there was flexibility on check in time, 4pm is pretty inconvenient when just traveling to Chicago for the day. Otherwise great place, and would recommend it to friends and family traveling to Chicago.

We enjoyed our last minute booking at The Villa Toscana! The house was a cool, eclectic space and located in Boystown, a bustling neighborhood with lots to do and see within walking distance from the house. Having a sink in the room was really nice, since the upstairs rooms all share one bathroom (as is detailed in the listing), and they provided a nice variety of breakfast items, which was above and beyond. Thanks Ashley!

Wonderful stay, with a great price and a great host!

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.

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.

The hosts are fascinating, lovely people who boosted our spirits during a stressful search for a house in the Chicago area. They serve a delicious breakfast, and even brought me a special treat with a candle when I said it was my birthday! The neighborhood is peaceful and the house is very comfortable. We didn’t find a house to buy, but we feel we found friends.