Dorothy's
Chicago
At a glance
Dorothy's Guesthouse is nestled in Chicago's vibrant Northalsted neighborhood, commonly known as Boystown. Northalsted is celebrated for its inclusive and lively atmosphere, thriving LGBTQ+ community, and cultural richness. Dorothy's captures this essence by offering a unique combination of charm and comfort that resonates with those seeking an engaging urban retreat.
The guesthouse features a selection of color-themed rooms, each designed to offer a distinct style and a high level of comfort. Whether opting for the Purple, Red, Yellow, or Blue Room, guests can expect thoughtful amenities that enhance their stay. The rooms incorporate a key-free entry system and include conveniences such as WiFi and a dedicated coffee and tea station available throughout the day. The establishment upholds a commitment to impeccable cleanliness and ensures each guest feels at ease through accessible communication and services.
Dorothy's Guesthouse also provides a serene garden area where guests can unwind amidst the greenery, while those wishing to explore beyond the premises will find themselves in an exceptional location. Situated close to Wrigley Field, it's an ideal lodging option for sports fans. Additionally, its proximity to the Addison train station offers straightforward access to downtown Chicago and other attractions via public transit.
The guesthouse’s location places it within walking distance to a variety of dining options, catering to diverse palates and offering opportunities to experience local culinary delights. With nearby cafes and eateries, guests can dine effortlessly in the neighborhood or venture further into Chicago’s broader culinary scene.
Serving not only as a resting place but as an inclusive haven, Dorothy's is particularly suited for LGBTQ+ visitors and allies looking to engage with the spirited ambiance of the Northalsted area. Its sister property, The Villa Toscana, provides additional accommodation options if Dorothy's is fully booked. Together, they embody a charming retreat designed with community and comfort in mind.
Reviews
I loved my trip. This location was so convenient and lovely. the parking permit was a god send, especially once set up for market days started and it was permit only parking. Breakfast was really good with a lot of options, the place was clean and I even got room services from sal’s pizza on my last night and it really came straight to my door which shocked me at home convenient it was. If i had any negative experience I would say it was other guests, not the bnb itself. some people don’t respect common areas and i wish there could have been a way to negate it but with there not being any staff, i don’t see how. in the end, this didn’t affect how i felt during my stay. i loved it and im already thinking about when i can come back!
If you just need a place to lay your head and can walk up stairs, dont mind sharing common spaces with strangers, and can pick up after yourself like a decent human being, staying here can save you a lot of money. If you want to be catered to or waited on, spend the $ on a hotel. Of the services offered (clean rooms & common areas, necessity-stocked bathroom, and continental breakfast), everything seemed well done and thoughtful. The central air was comfortable, and the room basic but clean, with closet, smart TV, and clean towels/linens. We were here on a weekday so it was pretty quiet, it will 100% be loud from the street on weekends or events, but this was a perfect cost-effective way to stay a night in Chicago!
Loved the location and the room and shared bathroom were clean. Outside noise went on pretty late into the night. Our sleep apps helped to cancel it out. Wished we could have met the cats! Breakfast area was nice and super well stocked. Appreciated how clean everything was!
Lively atmosphere at night for sure, with people out front having a great time. I stayed on the 3rd floor above the pizza place - Big Gay Sal's. There was a separate house next door, but I never made it over there because I had to get my car out of a garage in the morning. Breakfast was served over there. Maybe next time I'll check it out! Bed was comfortable, it's a small cozy room (mine was 33) with a clean bed and closet, overall exactly what I needed to not have to drive back very late at night. Charming common areas with a living room with tables and a TV, a full kitchen at your disposal, and a little balcony out back to relax on. This is a very old place, it has creaky floors and all of that. I loved it. It has a character all its own that you will not find in sterile, boring modern locations. The people staying in other rooms were pretty quiet, I tried to not be annoying when I got in late. I loved the quiet and laid back vibes that the place gave off. Check in included filling out an online form that you are sent - this I fully understand and you need to make sure you get that done. Using their thorough and detailed instructions made everything so easy. A code is provided upon the start of your stay, and the doors always operated as expected. There is a front door, a floor door, and your room door, all lockable. Room door, of course, also has a chain. I asked for and was left a parking pass, however I ended up getting a garage spot for the night via SpotHero so I left it unused per their request in their guide. But a free parking pass in Chicago upon request? Yes, please and thank you! Big Gay Sal's pizza was delicious at the end of my night - they stay open late on the weekends. Fast slices and they said they can even deliver right up to your room. On the room door there was a coupon for buy one get one draft beer too - cheers to that! It made waiting for an Uber that much nicer after driving for some time. I see other comments about ghostly happenings, but I encountered none and felt nothing out of the ordinary, and I lived in a haunted apartment for several years...I'm well aware of and sensitive to any kind of spiritual activity. I didn't have any inclination that something was there or happening. In my experience, when you do encounter something "ghostly", it can of course be unsettling, but go forward with a sense of curiosity, acknowledge it (seems that most of the time accepting it makes activity dissipate), and ask that it please move on and let you be in peace.
Dorothy’s was so cute and in a perfect location as we were in town for the Cub’s game. Only a 10 minute walk to the stadium! Instructions to get in were very easy to follow— you get your pin to get into the building right before your check in time. Everything was very clean. The only thing we couldn’t figure out was how to get the TV to work. Other than that, everything was perfect! Will definitely be staying here again :)
