The Villa Toscana Guest House

93% love it
Elegant & unique accommodations
In the heart of Boystown, Villa Toscana offers a charming Victorian-inspired B&B experience. Mere steps away lie the thriving nightlife of the city and within the walls, you will find divine comfort & relaxation.


    • shadowgwm
      shadowgwm Over a year ago
      Loves it

      You should check it out
      We stayed there a long time ago. Our experience was great. The owner and host was super friendly. He suggested places for our weekend. Much of it was spent in our room as I unknowingly had pneumonia and was feeling pretty rough. I would recommend it to a friend. Right on Halsted in Boystown, can't get better than that.

    • bill.vanhemert
      bill.vanhemert Over a year ago
      Loves it

      Great location. Ron, Inn Keeper, provided communication / coordination prior to our arrival, excellent host, and friendly. Guest house is charming, comfortable, clean accommodations.

    • wade.esser
      wade.esser Over a year ago
      Loves it

      had a great stay here
      perfect location to walk to all the nightlife and the rooms are great. friendly staff!!

    • utahboy
      utahboy Over a year ago
      Loves it

      A great place for gay guys to visit
      Had an unbelievably good time here in June 2013. Location is right in the middle of Boystown. Beautiful charming house (Victorian style) and clean, airy, pleasant. Breakfast was good, many choices. Ron the innkeeper is phenomenal; he took care of ALL of my needs ;)

    • terrist20
      terrist20 Over a year ago
      Loves it

      Great B&B
      My partner and I recently stayed here and had a very nice time. A beautiful house with may room motifs to choose from. Located right in the middle of Boystown, we found it to be a great location from which to walk to may stores, restaurants and bars as well as the train. Ron was the perfect host.

    • crboar
      crboar Over a year ago
      Loves it

      Muy céntrico, todo lo ambiente queda a la mano
      Hotel, con desayuno incluido muy aceptable, cereal, jugos , pan y fruta, ubicado en medio de la zona gay, todo te queda cerca, muy cerca la estación del metro que te lleva a la zona turística del centro , llegas en unos 20min. No es el más barato pero lo compensas con la ubicación, Excelente atención del propietario. Ojo el baño se comparte con los demás huéspedes, así que sí coincides con otra persona esperarás tu turno. . .

    • ChicagoNick
      ChicagoNick Over a year ago
      Loves it

      Excellent guesthouse for Gay Men
      I stayed here on three occasions over several months while applying for jobs in the Chicago and Evanston areas. I found it while web searching and decided to try a B&B instead of a chain hotel. Also I prefer staying in surroundings of other Gay men like myself. I was very pleased with everything! It is located on a busy street in the Boystown entertainment district. Parking can be a challenge but there will always be a space somewhere nearby. The manager will give you a parking pass when you check in., Very simple process. OK, so I stayed in three different rooms and loved all of them. Some have a private bath, some share a bath (upstairs rooms.) I was here in summer, early fall and early winter, a good mix of the seasons! There is an outdoor garden, good for sitting or cruising :) or for hanging out. It is on a main street and you can watch all the boys go by. It is in a safe and clean neighbourhood. The rooms are small and cozy and very clean. There is a nice common area for sitting, reading, having tea, etc. The kitchen is where breakfast is given from 6:00am and there is an excellent balance of foods such as cereals, fruits, yogurts, coffees, teas, grain bars, pastries, buns, etc. I was impressed with the array on offer and also the manager was there several times to clean and arrange during the breakfast hours for the good of the other guests (I swear, gay men can be so messy like yoiungsters at times, right, LOL?) There is also an assortment of juices in the refrig. They have free WiFi and it was blazing lightning fast! Check-in is speedy and efficient and they called me the day before my arrival (2 of the 3 times I stayed there) to confirm my arrival and to welcome me to the B&B. I appreciate this little touch. Ron the manager is very welcoming and answered all of my questions about the area and showed me all the amenities of the B&B. He was an encyclopedia of knowledge about places to go in Chicago, restaurants, bars, clubs, saunas, etc. He gives great attention to detail in all matters pertaining to the guests, a trait not always seen in small guesthouses these days. I was made to feel very welcome. Lastly, as a room tip, if you don't want a lot of street party noise, avoid Room 1 the Art Deco. I personally loved Room 8 the Morocan because it is private off the side of the breakfast room and had a nice comfy feel to it and a large private bath. Highly recommended!

    • Pancho_Miami
      Pancho_Miami Over a year ago
      Loves it

      Location is a gem!
      Stayed here November 2012. The best things about this guest house are its central location (within steps of Boytown's nightlife) and Ron, the on-site Manager (he is extremely helpful, knowledgeable, and friendly). There are also two train stations within walking distance if you want to explore the rest of Chicago.

    • wolfeyes_85
      wolfeyes_85 Over a year ago
      Loves it

      Awesome price, location, set-up, and staff!
      Currently staying in the guest house Morrocan room, love this place and you can't beat the location or the price! Definitely will return next time I'm back in town!

    • thtguy05
      thtguy05 Over a year ago
      Loves it

      amazing place
      i stayed here for a weekend get away with my bf. amazing place walking distance to all the bars and resturants in boys town..contherable beds, amazing staff, easy to talk too and really assesable kitchen. highly recomend to any couple looking for a nice weekend away from home.

    • dutchwim48
      dutchwim48 Over a year ago
      Hates it

      small rooms
      Stayed with my boyfriend in a basement room. A small room for a big prize. Staff was friendly.

    • geniusdevil
      geniusdevil Over a year ago
      Loves it

      The rain flooded the rooms in the basement. Quite unpleasant it turned out the first day but later the stay was enjoyable as i was moved upstairs. Its right in the village, beautiful, cosy, the couple who owns it is very sweet.

    • its4kito
      its4kito Over a year ago
      Loves it

      Great location
      Basic guesthouse. Basement rooms felt like a fire trap. Prefer upstairs rooms.

    • YvonJustinCote
      YvonJustinCote Over a year ago
      Hates it

      Rude Reservations
      I come to Chicago a few times a year and when The Majestic is booked I stay here. I stay because of the location mostly. I find the reservation staff abrubt and rude but normally just put up with it. Today different story I'm done with these guys. Terrible representation of such a beatiful friendly city. Phone manners aren't that difficult to learn.