Members-only rates
4.3 / 5 Excellent

Dorothy's

Dorothy's
Dorothy's – Chicago, IL
Dorothy's – Chicago, IL
Check in 4:00 PM
Check out 12:00 PM

About Dorothy's

Comfortable Accommodations Dorothy's in Chicago offers adults-only bed and breakfast accommodations with free WiFi, air-conditioning, and private bathrooms. Each room includes a tea and coffee maker, dining table, and TV. Convenient Facilities Guests can enjoy a lounge, shared kitchen, outdoor seating area, express check-in and check-out, room service, and luggage storage. Additional amenities include a washing machine and dishwasher. Prime Location Located less than 0.6 mi from Wrigley Field and an 8-minute walk to Brier Street Theater, Dorothy's is near attractions such as Fullerton Beach (1.7 mi) and Lincoln Park Zoo (2.1 mi). Midway International Airport is 14 mi away. Boating is available in the surrounding area. License Number(s): 2992700

Amenities

  • On-site dining
  • Express check-in / check-out
  • Luggage storage
  • Full kitchen / kitchenette
  • In-room refrigerator
  • In-room microwave
  • Pet friendly
  • Smoke-free property
  • Air conditioning

Reviews

4.3 / 5
Excellent 186 reviews
  • Engine customer Sep 2026

    The problem with not seeing the owners (ever) is that if there’s an issue, it’s not real clear how to resolve it. My room was a little musty, and had I seen someone at breakfast, I’d have likely mentioned that. I’d have also suggested a basket in the bathroom for the used hand towels. And they could probably start a pot of coffee in the morning (or at least instruct how much grounds to scoop for 12 cups). But overall, minor issues for a decent place at a good price in a safe neighborhood. Convenient to the El and several bus lines … an easy CTA trip from either airport. Recommended, and I’ll be back.

  • Engine customer Sep 2026

    Stunning courtyard, relaxing porch and sweet grey cats!! Instructions were easy to follow for access & luggage storage. Blackout curtains were a huge help as 3rd floor W was warm— another guest left something that spilled on our refrigerated items and towels in the bathroom, but it was convenient to have laundry machine access— we enjoyed our stay!!

  • Engine customer Sep 2026

    this was awesome but we had crazy ass dreams, pretty sure it’s haunted. super cute though!

  • Engine customer Sep 2026

    Space was so clean and modern. Breakfast was good also. Very nice stay.

  • Engine customer Sep 2026

    The room was extremely clean and nicely set up! The ac was tooo cold but other than that, Loved my 3 day-stay and would stay again!

  • Engine customer Sep 2026

    We didn't even check in because we got a message right before we checked in with more details and it said there were 3 cats that roamed the property inside and out. I am highly allergic so knew I couldn't even be there. We actually would like our money refunded for lack of that not being told when confirmation of booking long ago.

  • Engine customer Sep 2026

    Easy to access even without human contact once the system is understood

  • Engine customer Sep 2026

    The most aggravating check in experience I have had in 45 years of travel. This place is disingenuous at best.

  • Engine customer Sep 2026

    Thank you for everything

  • Engine customer Sep 2026

    👍

  • Engine customer Sep 2026

    Staff could have been present during breakfast to make coffee which needed to be done several times.

  • Engine customer Sep 2026

    Other than a little confusion getting in the front door, everything was great. Love the neighborhood and the proximity to Wrigley. Walked all around, by myself at night and felt safe.

  • Engine customer Sep 2026

    This place is amazing! It's located in a gay Chicago Neighborhood that is super friendly and clean. The building is super historic and the room was fantastic. They have everything covered. I felt at home and loved it. The customer service needs improvement. They send these links that are somewhat confusing at first. Some of it was definitely on me not figuring it out but the lady working treated me like a nuisance. She didn't want to take the five minutes to explain. Once the guy walked me to my room it was awesome.

  • Engine customer Aug 2026

    Great place to stay in the heart of Boystown/Wrigleyville. We loved the close distance to the Wrigley Field & all the bars. We had a blast, & the breakfast in the morning was just the cherry on top to a nice overnight getaway.

  • Engine customer Aug 2026

    The patio was a nice place to enjoy a continental breakfast. Small room but spacious living area adjacent. Good bathrooms and shower.

  • Engine customer Aug 2026

    Parking was terrible and no one on the staff was helpful. Breakfast did not have any staff to help with food,

  • Engine customer Aug 2026

    Can't say enough about our stay here. First time in Chicago and this is located in a beautiful, vibrant neighborhood and a 7-minute walk to the Red Line/Wrigley Field. The staff was communicative, and the room itself was clean, spacious, air-conditioned, and had everything we needed. Can't recommend Dorthy's enough. On the website, they warned about being in a noisy area; we did not find that to be an issue whatsoever.

  • Engine customer Aug 2026

    Walking distance to Wrigley, great neighborhood. Just basically slept there & got ready! Had everything we needed great little balcony out back, Great price. Highly recommend 10/10

  • Engine customer Aug 2026

    Parking is difficult. There is no front desk and contacting staff is not easy if you have an issue.

  • Engine customer Aug 2026

    Room was clean, but it’s a pet friendly location so random pet hairs were found -but also expected- which we weren’t wild about. Breakfast was 10/10! Location was excellent for our needs and would absolutely stay again.

Frequently asked questions about Dorothy's

Does Dorothy's have free Wi-Fi?
Yes, Dorothy's offers free Wi-Fi for all guests.
Does Dorothy's offer parking?
Yes, Dorothy's offers free parking on-site.
Does Dorothy's have meeting spaces, conference centers, or conference rooms?
Dorothy's does not list dedicated meeting or conference facilities. For business event venues in Chicago, see business hotels in Chicago.
Does Dorothy's have a fitness center?
Dorothy's does not list an on-site fitness center. Some properties partner with nearby gyms — check directly with the hotel.
Where is Dorothy's located, and how walkable is the area?
Dorothy's is located at 3445 N Halsted St, Chicago, IL 60657. With a Walk Score of 94, the area is rated Walker's Paradise. Most daily errands can be done on foot — ideal for travelers without a car.

What's nearby

Map of points of interest near Dorothy's
  • 875 North Michigan Avenue 3.5 mi
  • Chicago Merchandise Mart 4.0 mi
  • Trump International Hotel and Tower 4.0 mi
  • Haymarket affair 4.2 mi
  • Aon Center 4.4 mi
  • United Center 4.6 mi
  • Willis Tower 4.6 mi

Why no public rates?

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