Willows Hotel
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via Stay22About this place Willows Hotel
The Willows Hotel is a small, gay-owned hotel for LGBTQ+ travelers in Chicago, just a few blocks from the Boys Town action. You get a quieter, more residential spot but can still walk to the city's main gay scene.
Find it at 555 West Surf Street. The rooms are done up in a French Country style, all inside a building that’s a 19th-century reproduction. It doesn’t feel like a chain hotel, which is a good thing.
Because it’s a gay-owned bed & breakfast, the Willows gives you a more personal feel than the bigger places. It’s also positioned as good value, so if you’re trying to stretch your travel budget, this could be it. You’re right on the edge of Boys Town, meaning all the bars, restaurants, and nightlife are easy to get to, but you have a quiet place to come back to.
Chicago’s gay travel scene is strong and friendly, and staying somewhere like this means you’re with hosts who get it. The French Country look is for anyone who wants something with a bit more character than a standard hotel room. For more, check their website: willowshotelchicago.com.
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The place is very nice. A beautiful old building with character. Eric is a star employee super helpful and knowledgeable about the area. He definitely added to the positivity of the place.
Booked a room with them on the wrong day and they so generously worked with me to book the right day. I thought it was going to put a huge kink in our trip, but I’m so thankful that they worked with us.
This hotel is a walk back in history. Built in the twenties turned into a hotel in the '50s has the old historic vibe. Hotel has been updated but sometimes restricted by the architecture which they have accommodated well. The staff, particularly Eric and Roxanne, go out of their way to ensure your stay is second to none. If you're looking for the newest hotel with the greatest and latest amenities and newest of architecture, probably not for you. But if you're looking for hotel that gives you that great vibe of Old Town Chicago and what service was at a premium you could not pick a better place. Could not recommend this more highly.
Want to give a huge shoutout to Mia for being such a delight and being so accommodating! Truly the sweetest person! Everyone else working gave a lackluster experience to the trip! Would stay again for the chance to see Mia!
I booked this hotel for a girls trip and it was perfect. Really liked the location. The hotel is nestled in between apartment buildings and it was quiet and we felt safe. I would say the bed and pillows were a little lumpy and there was only free coffee/tea/water. No food. But the staff were friendly and we didn’t mind.
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Last updated on 3 August 2026