Dorothy's
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Dorothy's

Hotel
3445 N Halsted St 2 & 3, Chicago, IL 60657, USA
(800) 774-2348 · Ext 15307, then #
www.dorothysguesthouse.com

Nestled along the iconic Route 66 in vibrant Chicago, Dorothy's is a charming boutique hotel that invites travelers to experience the rich history and culture of the Mother Road. With its warm, welcoming atmosphere and thoughtfully designed rooms, this LGBTQ+-friendly guesthouse serves as a cozy retreat after a day of exploring the city's dynamic neighborhoods. Relish the vibrant local scene, just steps away from the bustle of Halsted Street, and enjoy a unique blend of comfort and community at Dorothy's, where every stay is a memorable part of your Route 66 adventure.

Top Reviews
Sean streck

Sean streck

3 months ago

"Didn't know what to expect with thus arrangement but it worked out. Enjoyed my stay and would consider it again. Some pros: Location is prime. The apartment is very secure. There's two full bathrooms for 4 rooms which is nice. Everything was clean and smelled nice. Some cons: Parking is rough as you might expect, especially weekends. Not my highest recommendation if you must drive/park. If you like really regimented and familiar check in, the way you check in might be stressful. Staff was helpful but checkin and figuring out parking was definitely a new one. The building is quite old and there were some nuisance problems with small things in the apartment but they didn't ruin the stay. Overall I'd say a solid option for a solo or couple traveling who need a no frills stop in the middle of Boys Town."

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Patrycja Mackiewicz

Patrycja Mackiewicz

3 months ago

"We really enjoyed our stay in the apartment. It had everything we needed. The only downside was the noise from the street, but the owners inform you about this before you arrive, so if the hustle and bustle of the street is a problem for you, you can choose a different location. We really liked being so close to everyday street life."

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James Gundersen

James Gundersen

2 months ago

"This is the place. First time but it sure won’t be the last. Wonderful room, in a great location for all your Chicago visit needs. Comfortable and clean, and an amazing neighborhood."

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Dorothy's | Route 66 Hotel in Chicago, Illinois