Penthouse Host - RM2 - The Most of Your Vacation, Steps to Bars

Troy

Response rate: 30% • Response time: a few days

Happy to share local tips

Penthouse Host - RM2 - The Most of Your Vacation, Steps to Bars

Name: Penthouse Host - RM2 - The Most of Your Vacation, Steps to Bars
Brand: misterb&b
SKU: 1023771
Price: 69.0 USD
Availability: InStock
Rating: 5.0 (5 reviews)

Chicago, IL, United StatesLGBTQ+ venues nearby•Map

Exceptional5.0(5)Booked 7 times

Private room

2 guests

1 Bedroom

1 Bathroom

1 bed

Clothing optional acceptedHappy to share local tipsLGBTQ+ venues nearbyGym nearby or in the propertyWi-FiBreakfast includedDedicated workspaceHot tubPets allowed

The Reveal

Near LGBTQ+ SceneInsta-WorthyRelaxingCentral location

Brand New Renovation - Uptown Penthouse Apartment - Steps from Gay Bars, Shopping, Dining, Transit, Theaters, Spa, and more. Centrally Located next to Boystown and Andersonville. Guest room has a full size bed, work desk, modern lighting, smart tv, black out curtains, and a shared bathroom bathroom is just across the hall. Large kitchen and two large balconies off the common areas, one has a semi-private vibe. All essentials are provided, and breakfast is always included... I am a realtor, artist, florist, chef, event planner, designer, etc and do lots of free lance work - can come up with a menu and set price to include all your meals. There are two dogs, Sophia and Rose, Black Lab Pit bulls. I can create the atmosphere you desire most for your vacation or work trip. From low key, tranquility to hosting After-Hours.

I have security camera(s) outside of my place

There are 7 traveler(s) looking at this listing!

How the beds work

Bedroom1 Double Bed

Little Luxuries

Clothing optional accepted

Happy to share local tips

LGBTQ+ venues nearby

Gym nearby or in the property

Wi-Fi

Breakfast included

Dedicated workspace

Hot tub

Pets allowed

The Classics

Wi-Fi

Dedicated workspace

Kitchen

Breakfast included

Air conditioning

Terrace

Garden

Washer

Essentials

Hair dryer

Dishwasher

Dryer

Iron

Heating

Hot tub

Outdoor dining area

Paid parking nearby

Sound system

Netflix

LGBTQ+ Favorites

LGBTQ+ venues nearby

Happy to share local tips

Adult Only

Gym nearby or in the property

Spa salon nearby

Welcome

Pets allowed

Pet owner

Clothing optional accepted

My location

Near beach

Near lake

City center

Near cultural venues

Fire protection

Smoke alarm

Carbon monoxide alarm

Fire extinguisher

LGBTQ+ Kinky Amenities

Meet Your Proud Host

Troy4.9(12 reviews)

Facebook verifiedE-mail verifiedPhone verifiedID verified

Member sinceJuly 2015

Response rate30%

Response timea few days

45 year old entrepreneur, artist, socialite, in Chicago. I spend a lot of time working.... lots of creative things; painting, T-Shirt company, organic soaps, novelty / promotional items. I'm a multi-family consultant that specializes in add value and reducing vacancy loss. Cooking, entertaining, hosting, theater, traveling. World Traveler - 41 countries

View profile

10 interests: Exhibitions & Museums / Movies / Musicals / Theatre / Cooking / Food & Wine / Gardening / Home & Interior Design / Pets / Volunteering

Protect your payments: never communicate outside of misterb&b (website or app) and never transfer money outside our secure system.

Select the dates of your stay

No dates selected yet.

September 2026

SMTWTFS

October 2026

SMTWTFS

Why Book Proud with misterb&b?

Travel with purpose. Support the LGBTQ+ community with every stay.

Your discretion is guaranteed

Your invoice and bank statement never show misterb&b.On your statement:PinkLab

Every stay gives back to the community

This booking will contribute to our Mister for Good program, helping LGBTQ+ NGOs around the world.

Built by and for the LGBTQ+ community

We're an LGBTQ+-owned platform. Your support directly funds jobs and livelihoods for our LGBTQ+ team.

Unlock the local gay scene

Meet LGBTQ+ locals with weere, discover insider tips and explore beyond your hotel.

Where It's All Happening

Chicago, IL, United StatesExact location disclosed after booking only.

LGBTQ+ Safety Score: Chicago

5out of 5Very safeRated by 5 local misterb&b members

Your Queer Map: Nearby Gay Hotspots

Full gay city guide for Chicago »

Gay RestaurantsFat Cat4840 N Broadway (at Lawrence Avenue)

310 m7-minute walk

Gay WellnessSir Spa/

504 m11-minute walk

Gay RestaurantsAndie’s5253 N Clark (between Berwyn & Farragut)

504 m11-minute walk

Gay RestaurantsSvea Restaurant5236 N Clark (between Berwyn & Farragut)

504 m11-minute walk

The social app from misterb&b

Free Gift

Enjoy 3 days free on weerePLUS with your booking

And instantly connect with the local gay community.

Discover weere

1464 active members around the city this month, ready to show you their favorite spots.

Discover weere

Nearby Attractions

The Baton, Meeting Room House, Banana Video, SoFo Tap, Atmosphere, Cell Block, Charlie’s, Fantady, Roscoe’s, Progrss Bar, Splash, Hydrate, Steam Works, Men’s Room, the Closet, Sugar Daddy Bakery, Gay Uncle Al’s Pizza, RePlay, Elixer, Marty’s Martini Lounge, Brown Elephsnt, Center on Halsted, Howard Brown Health

House Rules & Conditions

Check-infrom 4pm to 8pm

Checkoutto 10am

Host recommendations

No smoking of any kind on site.

Extra per guest$20 per night after 1 guest(s)

$20 per night after 1 guest(s)

Minimum stay (nights)1 night

1 night

Cleaning fees$25 USD

$25 USD

Deposit$100 USD

$100 USD

Registration numberR23000090364

R23000090364

Cancellation Policy

Terms of Services & Privacy Policy apply to this transaction.

Add dates to get the cancellation details

ReviewsExceptional5(5)

Reviews come from verified guests, are sorted chronologically and not subjected to prior monitoring.

Cleanliness4.8

Location5.0

Accurate description5.0

Check-in4.8

Value for money5.0

Our Community Has Spoken:

BrianStayed in June 2026

Reviewed on July 01, 2026

Great location - was easy to walk to most of the different locations for the events I was attending while in Chicago. Troy is a fantastic host, and his pups are super sweet. Definitely will consider staying with Troy again in future trips to Chicago...

DekotaStayed in March 2026

Reviewed on Mar. 10, 2026

His place was lovely and comfortable and made me feel right at home with all the goodies and food he provided throughout the stay. I grew to love the dogs Sophia and rose very sweet babies. I would recommend staying with Troy if you want amazing food and a great location to all the bars in Boystown Chicago as well as Andersonville.

KalayvanStayed in October 2025

Reviewed on Oct. 29, 2025

I had such a great time staying here! Troy's place was absolutely beautiful — super clean, comfortable, and had a really nice vibe. Troy was amazing and super helpful. He gave me great recommendations for bars and fun things to do around the area, and even hooked me up with some discount codes, which was awesome. Really appreciated how friendly and welcoming he was. Definitely one of the best hosts I've had — would 100% stay again!

deHilsterStayed in October 2025

Reviewed on Oct. 14, 2025

Another lovely stay. And crazy adorable Sophia and Rose. Love them both so much. And Troy's cookies were delish

CaetanoStayed in September 2025

Reviewed on Oct. 02, 2025

This was the most perfect and quiet location just close enough to all the action of Boystown and Andersonville. Argyle is right up the street and has lots of great food options, but any questions you have Troy will be able to answer. He goes above and beyond as the nicest host, and will also give you your space. His two dogs are the sweetest, can't recommend staying here enough!