The Villa Toscana Guest House

I'm super grateful 🙏 that I found this adorable and extremely cozy B & B hidden away from Halsted street. I decided against renewing my apartment lease in Lakeview and I've been a nomad in the Chicagoland area since September 5th staying in various pet friendly hotels within Evanston and Schaumburg. |It was super nice to discover Villa Toscana in my old neighborhood and my pets really enjoyed the ambiance of a home environment instead of a hotel vibe. |This Victorian home 🏡 is extremely cute with beautiful furnishings so my pets felt safe. A sweet pomeranian even greeted my cat and dog and the three interacted beautifully in the living room area. |I chose the wandering room because I have a large pyrenees service dog and I'm so happy I did because both of my fur babies had ample room to sprawl and there was a roll away bed, two cute antique chairs, beautiful lighting, a chandelier, and a very beautiful antique bed with beautiful velvet sheets and an extremely comfortable mattress. |I wasn't extremely thrilled with the cable TV options because it didn't have the channels i normally watch but the room itself exceeded my expectations. |I also had issues with my smartphone wifi because I normally like sleeping with my music selections on YouTube but the wifi here kept competing with my Verizon wireless wifi.|Breakfast is fruit on the countertop, various cereals, bread, pb & j self serve or you're welcome to cook your own breakfast if you bring in groceries. I'm not a breakfast person so I saved my appetite for the Chicago Diner which is a vegan restaurant just a few yards away.|My second night here i accidentally locked myself out of my own room and forgot my room combination code. It was about 5:30 AM and I was absolutely embarrassed but hey stuff happens and it taught me a huge lesson because I had to wake up a guest across the hall from me and he had to wake up Brandon who wasn't even angry at me. Folks if you need to use the bathroom in the middle of the night 🌙 Don't close your door all the way shut and or make sure you don't push in the button from the inside of your room.|Fortunately I was allowed a late check out. I had a ton of things and the extra time was appreciated. If the house hadn't been booked for a private party I would have extended my stay here. Also the bathroom is incredibly clean and there's an antique clawfoot tub to shower or bathe in. I was initially worried about sharing a bathroom with other guests but there weren't a lot of people on my floor and I had the bathroom mostly to myself so it felt private.|All in all the neighborhood is fantastic, the other guests here were super sweet and my dog Troika found a new Friend to play with.|If you need a very reasonably priced B & B in one of the liveliest neighborhoods you should give Tosca villa a try.

Great location and friendly staff. Great option for post concert overnight. Chuckles the dog is bonus treat! Rooms are comfortable and clean. Recommend lower floor with private bathroom versus shared. Outside court yard adds charm to overall experience. We did not stay for breakfast so cannot comment. ||Steve and Renee

I was first met with quaint paintings of dogs in Victorian-style dress, along with a delicately distressed picture of potted flowers. The breakfast was divine, with perfectly aged Lucky Charms, each piece chewy like a gelatinous form. The bed sloped down like the pristine slopes of the Swiss Alps. The bathroom, incidentally trapezoidal in shape, had an ethereal and almost haunting quality. The ambient whirring of the fan provided a beautiful sonic backdrop for my morning routine. The sound replicated the mating calls of ravenous falcons splitting through cool spring air. To address the stark controversy in other reviews, The Villa Toscana has repaired the banister since a former guest took an unfortunate tumble, claiming with her the decorative newel cap atop the banister by the stairs. The necessity to procure my own parking exposed me to a wider array of what the city had to offer. In the end, Villa Toscana is an aged relic nestled into the bosom of downtown Chicago.

Quirky bed and breakfast centrally located in Boystown. Location is great. Easy walk to Lincoln Park and environs. Rooms with private bathrooms are located in the basement, adjacent to the main home. My basement room, Room 6, was small but comfy. Bedroom and bathroom were clean. Breakfast on Friday was sparse. Thankfully, there is a great café 700 feet to the left! Check-in and check-out were virtual and seamless.

I regret ignoring the bad reviews I read about this place. We were notified just a few hours before our check in that there would be 15-20 college students filming on the property until 9pm, well after we had to confirm our stay. We get there and the front door is wide open, garbage is everywhere, and the students were apologetic because they didn’t even know people were actually staying on the property. I understood that this would be a self check in place, but it seemed very careless to not make an exception and have at least one staff member on the property when there’s an additional 15-20 students there to make sure things were somewhat clean inside and to ensure the security of the place. The living room and kitchen was packed with people and their food and equipment, our shared bathroom was also being shared with 15-20 other people. Obviously this is a unique situation, but the way it was handled by the staff was very disappointing. The security of the house was a concern of ours and we didn’t really have access to any of the amenities outside of our room so why we were paying the full price we were paying seemed ridiculous (we were not told of the filming crew until after we had confirmed our stay, we would have had a few questions before confirming if we had known beforehand!). The staff member I spoke to on the phone said “well we’re pretty much always booked so we’re not concerned about bad reviews”. Cool, so you guys can laugh at this one! We ended up booking a hotel room last minute because we would have rather wasted hundreds of dollars than stay there with the fear of finding some creep in the shared bathroom in the middle of the night who snuck in because there would have been nothing stopping them from doing so!

The room is very small, but worked very well for my wife and I. Excellent location in downtown Chicago. Very safe neighborhood. So many restaurants and bars very close. Parking was fine but difficult to find. Would highly recommend staying here we will be back!

I recently stayed at this property during a road trip to Chicago, and while the price seemed like a steal at first, my experience was far from ideal. First, the **parking situation** was a big issue. On Booking.com, it was stated that there is "free street parking" and "parking on site." This turned out to be quite misleading. After circling the block several times trying to find parking, I was eventually told there is **no parking offered by the facility**, and street parking isn’t technically free. You need a parking pass (provided in the room) to park overnight, but this information was not clearly communicated ahead of time. If this had been mentioned on the booking platform, it would have saved me a lot of hassle. As for the **rooms**, they were just okay—nothing special. I’ve stayed in far better Airbnbs for only $20-$30 more. The **washrooms** were decent, and the **breakfast** was average at best, with nothing particularly memorable or special about it. Overall, for the **price**, I didn’t feel it was worth the money. If I had known about the parking issues and the underwhelming experience, I would have just booked a motel or an Airbnb instead.

Villa Toscana was an amazing place to stay in the heart of Boystown! The room was clean and comfortable and it was very clear on how to get in touch with the owners if needed. Check in and check out was very easy and I was able to do all of that online so very convenient. We received multiple emails leading up to our stay that allowed for special requests (such as requesting parking passes) and also included a very clear map on where we were okay to park. The little garden in front was very tranquil and pleasant to sit and relax in. I cannot speak highly enough of the villa and the owners - we will definitely be back next time we come to Chicago!

Management is not on site, so: 1. The property is not kept up, so the pictures on their website are misleading as to the actual condition of the property. My room was held together with caulking, extension cords and power strips plugged into other power strips, and a random brass plate covering a hole in the wall. The smoke detector was also covered with a plastic bag and tape. 2. Registration and check-in is by email and text, and management cannot be bothered to take phone calls. So instead they inundate the guest with text messages and emails (a total of 15 from the property to me, including texts from two different phone numbers) regarding the reservation, registration, and check-in. I tried to check in using a text message that had only the door code but couldn't find my room because you book your room by name (e.g., Venetian Room) but when you arrive, the rooms are numbered. So I texted manager Ashley, who ended the text with "Considering 99% of people don't have problems maybe it's not us that's the problem." Never before in my life have I have been talked to like that by someone (supposedly) in the hospitality industry. Ashley is passive aggressive and has no business working in any customer-facing position, much less in the hospitality business. And apparently she's rather immature, because she's not learned that having to have the last word is not a becoming quality, especially with guest when her intent is incite and/or insult them further. I would rather sleep on the streets of Chicago than stay at Villa Toscana again. Do you yourself a favor and stay at a real hotel in Chicago.

For the price, this place is worth it. Our room was small, but clean. Location is great and outside of the house is super cute. The biggest complaint is their hospitality. I have never seen a more passive aggressive hostess in my life. Check in instructions literally read "if you are having trouble checking it, we know you didn't read our instructions." They even said do not contact us unless it's an emergency and yet their locks were broken so we couldn't even access our room. Brandon was extremely nice and responsive but the other host didn't say hi and was beyond unfriendly it blew my mind.

this place has some rude lady name Maggie that runs it. she's a lier and try's to scam people and the villa is a total dump. all the updates that have been done to this place with the added bathrooms and room conversions look like they were done by a child or someone with zero skill. nothing is up to code and nothing was done correctly. the city should really shut this place down. She frequently has one price online after it's booked she will try to change the price and claim it's an error on the discount hotel website that happens nearly everyday. She says they offer a breakfast included But they had absolutely no breakfast.

Was better then I could of imagined. Great location and so friendly . Beds perfect and host more than helpful. Can't wait to go back!

Location is great, I'll give it that. My room was subterranean, small, grim, badly decorated. Every noise at the entry door, dogs of guests, children of guests was noted all through the night. During pandemic, the grab and go breakfast consisted of a loaf of white bread, a bowl of apples, and a jar of peanut butter. We encountered the owner on our departure. He was crabby, critical, and generally a jerk. I think he forgot that it is called the hospitality industry. Would never recommend under any circumstances.

The room was clean and new. Staffs are all friendly and accommodating. I find it very nice and good for people taking vacation. Good thing, hotel is near a bus stop. That is a plus. Overall, good experience. I was so happy seeing my family enjoyed the day. Thank you so much for accommodating us!

We had a great time at the Villa. Firstly, it is smack dab in the middle of "Boystown" which was a lot of fun! There are walkable bars, Wrigleyville is a quick 10 minute walk and it is a prime people watching location. The con of this is that you can definitely hear street noise and partiers up until 2-3am especially if you have the front facing room like we did. The room is basic. The bed was supppppperrrr comfy! The bathroom is shared between 3 rooms and that was never a problem. In fact, we barely saw anyone upstairs and saw a few people at breakfast. The breakfast is basic but good. There is a wide assortment of whatever you would want for breakfast minus any hot foods. Ron, the innkeeper, is definitely not friendly AT ALL. But who cares? We weren't there to get to know anyone else. The Villa is reasonably priced and you get a good place to stay for the price. It does appear a bit rundown (bathroom sink handle fell off a few times, the shower leaves a lot to be desired)--so if you're looking for a place of luxury and R&R I'm not sure this is the place. If you're looking for a place that will give you a bed and bathroom (and breakfast) so you can spend most your time away and exploring--this is the place for you!

I had a lovely time here, and it was a great place to stay for a first-time visitor to Chicago, especially for my gay self and my gay husband, as it's in the middle of Boystown, Chicago's gay neighborhood. If there were any cons, it would be the lack of lighting above the mirror in the bathroom (a little nitpicky I'll admit, but beautifying my face is much easier with the proper lighting!), and an often frustratingly weak wifi signal. But those are very minor complaints. This place is *very* quiet due in large part to being recessed from the street, behind a beautiful courtyard, between two much larger buildings. Once inside it almost feels secluded, although there's a balcony on the side of the building from which you can find others occasionally climbing the wooden staircases affixed to the backs of neighboring buildings on either side of the block. In our experience, such people were very friendly. (I found this to be the case of Chicago overall, actually -- at least in both Boystown and downtown.) Ron, the guy who runs the place, was very attentive, waiting until after office hours end if your flight lands later than 6 pm. He sets out a continental breakfast in the shared kitchen every morning between 6 and 11, and there is a plethora of cold-breakfast options (I ate a lot of cereal and bagels), way more than I've had at many conventional hotels. The upstairs rooms share a bathroom but the basement rooms, where we stayed, have their own private bathrooms. (I have no idea how the lighting in the upstairs bathroom compares but I guess getting a private bathroom is a fair trade.) The location is fantastic, on the same block or within just a few blocks of countless Boystown nightclubs and bars and restaurants. My husband and I are vegetarian and there is even The Chicago Diner, a vegetarian place, all of a couple of blocks away. It's maybe four blocks from the nearest "L" transit train station, on which we found it ridiculously easy to get around town. (Tip on that: get a multiple day pass for unlimited usage.) If I ever return to Chicago I might just stay here again.

My husband and I spent two nights at The Villa Toscana. Our first B&B experience. We stayed in The Empire Room or room#2. It was located across from the shared bathroom. Although, a shared bathroom is a new experience for us, surprisingly we were never inconvenienced. We will most definitely go back. Location is fabulous. Especially if you like great food, good drinks and Cubs baseball. Walking distance to several different places of interest. Upon EARLY arrival, we were pleasantly greeted by Ron, the Inn Keeper. He not only had our room available, showed us around the property and explained any and all questions that we had, he also gave us great insight on where to dine. Even though the house was at capacity it was very quiet and private. We did have the opportunity to have short conversations with other occupants, usually during included continental breakfast hours. All seemed as pleased as we are. We look forward to returning very soon.

The location of this bed and breakfast is absolutely amazing!!! The home itself is very clean and up to date. Ron who takes care of the house is phenomenal in his own right.... To start our already late flight from NYC was delayed by an hour and we didn't check in until 1 am. Ron waited up for us and made us feel extremely welcomed. He's also very knowledgeable about the area and will have an answer for any question you may have. I can not say enough good things about this place and will be booking any future visits to Chicago at the Villa Toscana and would recommend anyone else to as well.

You could walk pass this place twice and miss it. In fact, our son did. It's a small Victorian tucked back off the street in the "fabulous" north Halsted neighborhood. We stayed upstairs (shared bathroom) in the front room. Nicely sized, comfortable bed, TV. You could definitely hear when someone came up or down the stairs and there was a bit of noise from the main drag when the bars closed but, it is the city after all. Friendly not-intrusive manager. She had no problem with us hosting a bottle of Champagne and tidbits with another couple in the main floor living room before we went out for dinner. The price includes a parking pass for the neighborhood (You may get lucky and find one, we did), access to a well stocked kitchen with several self-serve breakfast options and wi-fi. I'd stay there again, for sure.

Had the occasion to stay here again hosting a couple of friends from Wisconsin. Once again a very pleasant stay, this time for two nights. Ron the innkeeper was his usual friendly self. He is such a sweet guy and made our stay everything it could be. He even went out to get hot bagels to go with our breakfast. He is the BEST!! The place was immaculate and we had the whole house to ourselves as we were the only guests on this snowy weekend. So much bang for the buck. We will absolutely be back!

What a gem! Nothing is closer to everything on Halsted. Room was cozy and clean. Hosts were very friendly. I would wholeheartedly recommend this spot and will likely be back again myself!

A hidden gem! Ron the innkeeper was more than accommodating and breakfast in the main house made us feel at home. We will definitely be back!

The high-rise we live in recently had to shut our power off for 12 hours while they replaced our generators. This would occur between 9am-9pm. So, we went looking for a place that would accommodate an early check-in of 9am. We contacted Villa Toscana to see if they could accommodate us. The date we needed was Apr. 12. We contacted them a month in advance. Today is Apr. 15. We still have not heard from them. Yikes!! Not only is that dreadful customer service, it's a loss of income on your part. Can't imagine that this place is run any better than that.

Great location in Boystown, free street parking passes, close to the red and brown line trains. small and cozy.

We loved it here. It's an oasis in the middle of Boystown. The location is what sold us to try it, but the villa itself is very clean, the accommodations are great, and the price was right! Ron is also a great host - welcoming and thorough but also unobtrusive. We'd stay here again in a minute!

It's true, all of the rooms in the (above ground) house part don't have their own bathrooms... only the themed rooms in the basement (which are smaller than their photos appear) have personal bathrooms. If you can deal with that... then, the location is perfect... offset from the street with a lovely old tree shading a green space with a few seating areas.

We stayed in the English room (garden level with own bathroom) for three nights. It's good value for the money. The bed was very comfortable. The TV was little small and the bathroom was on the basic side. But with a location like that, it's not like you're going to book in and watch TV all night, anyway. There were plenty of breakfast options available (fruit, muffins, bagels and spreads, cheese, juice, coffee, etc.) and I liked the relaxed, non-intrusive approach of the staff.

This place is GREAT. Rooms are comfortable and clean. Great outdoor covered front porch to sit on and have coffee, and the next door neighbor was friendly and let me play with his dog!! Right in the heart of boys town and next to the BEST vegetarian Restaurant I have ever eaten at CHICAGO DINER. Highly recommend this Gay B&B. I had a room in the downstairs and did Not hear any street noise at all. The staff is very friendly and helpful.

This is a very well located B&B in "Boystown". Unfortunately, that is the only positive about it. I have stayed in well over 100 hotels and B&B and this is at the bottom of my list. I have also never before written a negative review. Consider staying 2-5 blocks away in one of your other choices. The onsite proprietor was very unwelcoming. He had an awful attitude and only communicated the most minimal amount necessary, not just to us but to other guests from what we saw on day 4 when we checked out. Other than check in, this is the only time we saw him. Rooms 4-7, the "garden rooms" are basement rooms. Doors slam very loudly. There was no temperature control in the room. Bathroom had minimal light. No exterior light in bedroom as the very small glass block window and small 2nd window were barely above ground. The room (#5) felt like a fire trap. I have never before been in a B&B where there was barely a breakfast. On the counter there was coffee, cereal, a bit if bread and plastic-wrapped muffins. Since the manager barely spoke and was impossible to find, it was't until day #4 I opened the refrigerator and saw a few more breakfast choices. An orientation would have been nice. Among the many other negatives were a bad attitude about giving parking passes, even tho they advertise parking. In summary, I have traveled to over 35 USA cities and 30 countries, and Villa Toscana is at the bottom of my list. All the physical problems with the place would have been fine had the proprietor learned words like hello, thank you, can I answer any questions, and had he just been visible now and then. We have choices in where to stay in Boys Town and this is not the place.

I am thankful for the Villa Toscana to have availiblaity. rooms for the week I was there, every other hotel, within a 15 mile radius was booked, under $400. So I was grateful. The rooms were clean, the bathroom, shared, was a little leary, but never was a issue. Ron, I can see how others felt, but I am very friendly, and I had conversation every morning with him and another guest. With being a first time visitor to the Chicago area... Is very centrally located. If I were going for peace and quite, and in bed by 10, yes, there were close by activities. But once I hit the pillow, I heard nothing. I was in the center room upstairs. As for the breakfast, he supplied coffee, teas, and lots of things to choose from... And even commented on how organized and clean he was.. which was a plus, for me.... We even chatted about his plans for improvement, and he seemed excited. he loves his B&B.. Helen

A cozy bed and breakfast on Halsted that I would like to recommend to most anyone.

First, the good: Clean, fairly priced, air conditioned, fine continental breakfast, nice garden walking in, plenty of ice from the ice maker in the main fridge, adequate light, wi-fi works fine. The not so good: Extremely small room (Venetian Room) with no work area (chair next to table). No place to sit and watch TV (if you sit on the bed and lean back, it rolls away from the wall and you fall over backwards). Very stingy with supplies - toilet paper barely enough to suffice, wasn't replenished when room was serviced. Impossible to reach staff - left messages to get a blanket, finally had to call the emergency number before anyone responded. We never found anyone in the office, except to collect our money when we checked in. Air conditioning cannot be controlled, except by placing heavy objects over the registers. This room, like many others, is in the basement with tiny high windows. Bottom line: We will stay somewhere else the next time we visit Chicago.

I recently completed a 3-night stay at Villa Toscana. While the location was perfect and the room quaint, I would never stay at this establishment again due to the rude, unprofessional behavior of Ron, the "innkeeper." Ron made our stay incredibly uncomfortable with his unfriendly behavior and making rude comments. The following is a sampling: * Upon arrival, I was informed that we would be sharing a bathroom. While this was not a big deal, I did comment that I was surprised as this was not listed in my contract. Ron immediately became defensive and repeatedly stated that it was made clear on the website. I disagree. Again, it was not a big deal. Just be aware. * During our stay, the toilet in the shared bathroom became clogged. I'll spare readers the details, but I can say with absolute certainty that no one in my party had anything to do with this. However, Ron made it a point to directly accuse a member of my party for being responsible despite no evidence of this. Also, while informing us that the toilet was out of order, we did not appreciate his tone. It's been a long time since I've had someone speak to me in such a caustic tone, particularly for no reason. Neither I nor those in my party appreciated being spoken down to or accused of this. In any other establishment, I'd assume the staff would be apologetic if any of their accomodations were unavailable. * Upon checkout, he stated he would be inspecting our room. I should mention that there were other guests there at the time who expressed being surprised because their room was not inspected upon checkout. After inspecting the room, he said "Okay, gentlemen - you have two options. You can either go back up there and clean the room, or I will be charging you a $150 cleaning fee. The way you left that room is just rude and disrespectful." First of all, nowhere was it stated that we were expected to clean the room. In fact, they have a maid clean the rooms every day. Regardless, we had gathered all of our trash into a pile since there was only one small trash can. I don't believe we should have been responsible for cleaning the room without having been informed of us on the website, in the contract, or during check-in; however, if this is an uncommunicated (and, apparently, selectively enforced) policy, I think it could have been stated to us in a far more polite manner. * This one is very minor, but every time we would run into Ron in the house he went out of his way not to acknowledge our presence. When one of us would say hello to him, he would take a good three or four seconds before responding with a terse "hi" as if he couldn't be bothered. This is just a sampling of how Ron made our stay very uncomfortable. I travel quite frequently and have stayed at both high-end and low-end hotels, hostels, and other bed and breakfasts. This is certainly the rudest behavior I have ever encountered from staff and would rather pay more money or stay somewhere less convenient than to have to endure this sort of treatment at an establishment I am paying for.

Great B&B, had a wonderful stay. The Villa is clean and comfortable, great decor, Ron was more than helpful. It was really pleasant all around. I will definitely be back!

I travel alot. Alot. This place impressed me for the people's lack of interest in us as paying patrons and the apparent misanthropic misplaced career choice of the innkeeper. The basement room made me feel sick. No opening windows no way to control temperature. And dang, it was noisy. Basement had four rooms. People arrived back after bar time at three to five am and doors slammed and conversation seemed to happen upon our pillow. I longed for a table in a public laundry.

i've stayed here twice over the years: the location can't be beat and the price is right. i do wish they'd upgrade the plumbing in the main house (shared) bathroom. the shower barely trickles water and the sink drain is impossibly slow. and depending on the time of day, there can be precious little hot water.