Your Home in the Heart of Boystown

Welcome to Dorothy's Guesthouse

Experience the charm, comfort, and inclusivity of Chicago’s vibrant Boystown neighborhood.

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high comfort rooms

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Discover Lakeview

Nestled in the heart of the Lakeview burough, Chicago's Boystown neighborhood, now officially recognized as Northalsted, is one of the most vibrant and inclusive areas in the city. Located on the North Side, Boystown is renowned for its rich history, thriving LGBTQ+ community, and a lively atmosphere that draws visitors from all over the world.

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A gold and rainbow pylon in Chicago
#Ally

Dorothy's is proud to service the lgbt community.

Picture of Villa Toscana building
Our Sister Guesthouse

The Villa Toscana

Dorothy's totally booked? Check out our sister bed and breakfast.

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What Our Guests
are Saying...

(Swipe for more reviews)

Incredible and unique experience!

Everything was really clean and was really comfortable. Remember to bring your own shampoo, conditioner and other self cleaning stuff you might need. Everything was really well explained so you’ll never feel lost with something. Highly recommend!

Sara S.

Great Getaway

This was such a pleasant place to retreat to after enjoying the hustle and bustle of the city. They’ve created a little oasis with seating inside of a garden, quaint rooms, and surprising privacy. The communication is impeccable and you have all that you need for the perfect experience.

Nina W.

Great Spot Near Wrigleyville

Location, Location! This is a perfect spot if you are attending any event at Wrigley Stadium. Just about a 10 min walk to there and the Addison train station if you want to go downtown. The care taker was very attentive. The room was cozy. Loved the ease and security of the code locks. Lots of great places to eat with in walking distance. Breakfast was continental. Loved the coffee station downstairs.

The Skalet Family

Location, Location, Location...

If you want a clean, co-operative, really cool place to stay for a night or a week, this is the place. Great location (<1mi to Wrigley)! Easy access to the “L” and CTA busses. Small, but clean and continental breakfast. Reasonable rates for what they provide imo.

@popsx5

THE place to stay in the area

It really is THE place to stay in the Boystown area. I've been coming back for over 20 years and the recent owners are making several great upgrades. New amenities in the rooms like a retro fridge! I really like the all digital building and room access - no more keys!

William R
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Dorothy's Guesthouse
Amenities

Wifi
Room Service
Coffee/Tea All Day
Key-Free Entry
Self Check-In
Garden Access
Bag Storage

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