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Dorothy's

3.0 star property

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Photo gallery for Dorothy's

Free WiFi, bed sheets
Shower, hair dryer, towels, soap
Full-size fridge, microwave, toaster oven, cookware/dishes/utensils
Living area
Free WiFi, bed sheets

Reviews

8.4 out of 10
Very good

Popular amenities

  • Breakfast included
  • Pet friendly
  • Kitchen
  • Laundry
  • Air conditioning
  • Free WiFi
$86
includes taxes & fees
Nov 17 - Nov 18

Explore the area

View in a map
3445 N Halsted St, Chicago, IL, 60657
  • Place, Lincoln Park
    ‪8 min walk‬
  • Place, Wrigley Field
    ‪8 min walk‬
  • Place, Vic Theatre
    ‪9 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪23 min drive‬

Room options

View all photos for Basic Single Room

Free WiFi, bed sheets

Basic Single Room

9.0 out of 10
Wonderful
(4 reviews)
  • 54 sq ft
  • Sleeps 2
  • 1 Double Bed

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

  • 50 sq ft
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

  • 48 sq ft
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

Free WiFi, bed sheets

City Single Room

  • 50 sq ft
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

8.0 out of 10
Very good
(1 review)
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Apartment

Free WiFi, bed sheets

Basic Apartment

  • 1197 sq ft
  • 4 bedrooms
  • Sleeps 9
  • 2 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

View all photos for City Apartment

Free WiFi, bed sheets

City Apartment

  • 5 bedrooms
  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

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About this property

Dorothy's

3-star B&B in Lakeview
Along with a microwave in a common area, this smoke-free bed & breakfast has a refrigerator in a common area and laundry facilities. Free continental breakfast and free WiFi in public areas are also provided. Other amenities include a TV in a common area. Housekeeping is available on request.
Dorothy's offers 7 air-conditioned accommodations with shared/communal kitchens and hair dryers. Guests can make use of the in-room full-sized refrigerators/freezers and microwaves.

Bathrooms include showers. This Chicago bed & breakfast provides complimentary wireless Internet access, with a speed of 25+ Mbps. Housekeeping is provided on request.

Guests can enjoy a complimentary breakfast each morning. Wireless Internet access is complimentary. This Chicago bed & breakfast also offers laundry facilities, a communal living room, and a microwave in a common area.

Dorothy's is a smoke-free property.

A complimentary continental breakfast is served each morning between 6:00 AM and 10:00 AM.

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 25+ Mbps
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free offsite parking within 0.2 miles
  • Street parking available

Food and drink

  • Free continental breakfast available daily 6:00 AM to 10:00 AM

Things to do

  • TV in common areas

Family friendly

  • In-room full-sized refrigerator/freezer
  • In-room microwave
  • Laundry facilities

Conveniences

  • Laundry facilities
  • Luggage storage
  • Shared microwave
  • Shared refrigerator
  • Virtual front desk

Guest services

  • Housekeeping (on request)

Accessibility

  • 30 steps to reach entrance
  • No elevator

More

  • Communal living room
  • Smoking not allowed

Room amenities

Bedroom

  • Bedsheets provided

Bathroom

  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Food and drink

  • Cookware, dishware, and utensils
  • Freezer
  • Full-sized refrigerator/freezer
  • Meal delivery service
  • Microwave
  • Paper towels
  • Restaurant dining guides
  • Shared kitchen access
  • Toaster oven

More

  • Air conditioning
  • Heating

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: 10:00 PM
Early check-in subject to availability
Early check-in is available for a fee
Minimum check-in age: 18

Check-out

Check-out before noon
Late check-out subject to availability
A late check-out fee will be charged

Special check-in instructions

There is no front desk at this property
Guests planning to arrive outside of normal check-in hours will receive an email within 48 hours before arrival with check-in instructions and an access code; access will be through a private entrance
Prior to arrival, you must complete online registration via a secure link
You will be asked to provide the property with a copy of your government-issued photo ID after booking
If you are planning to arrive after 10:00 PM please contact the property in advance using the information on the booking confirmation
A virtual front desk provides assistance to guests

Access methods

Access code, private entrance

Pets

Pets allowed for an extra charge of USD 25 per pet, per stay
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

Optional extras

  • Pet fee: USD 25 per pet, per stay
  • Service animals are exempt from fees
  • Early check-in is available for a fee (subject to availability)
  • Late check-out is available for a fee (subject to availability)
  • Housekeeping fee: USD 5 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards and debit cards; cash is not accepted

We should mention

This property does not have elevators

Property is also known as

Dorothy's Chicago
Dorothy's Bed & breakfast
Dorothy's Bed & breakfast Chicago

Dorothy's Reviews

Reviews

8.4

Very Good

Rating 10 - Excellent. 50 out of 93 reviews
Rating 8 - Good. 23 out of 93 reviews
Rating 6 - Okay. 8 out of 93 reviews
Rating 4 - Poor. 7 out of 93 reviews
Rating 2 - Terrible. 5 out of 93 reviews

8.8/10

Cleanliness

7.8/10

Staff & service

8.6/10

Amenities

8.4/10

Property conditions & facilities

8.6/10

Eco-friendliness

Reviews

10/10 Excellent

Joshua

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in Aug 2025

10/10 Excellent

Connor

Stayed 3 nights in Jul 2025

4/10 Poor

John

Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

4/10 Poor

Gary

Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort

Not the Best

Said they had parking was street parking and the streets were packed. The feeling was breakfast like a B&B but cereal, waffle maker and some pastries and no coffee made, empty pot. Security is like a prison. lock boxes everywhere. 3rd floor, steps. More of a hostel than a hotel. They had a 4pm check in. We found a parking place 20 minutes before 4 and I asked for my code to get in and they refused. It came at 4. The place was old, the room tiny and it was not cheap. I would not go here again. No one there so you have to do things for yourself. You have to go online and fill out registration which includes picture of yourself and you drivers license because no one will be around. A hassle I have never experienced with a hotel. I had trouble getting to their websites cause their attached web address's were not links. I had to write them down and type them into my phone. Tried on my computer but you can't copy a picture into their site for the drivers license. You have to take a live picture and my computer didn't like that. Just aggravation that you don't need at the price of a decent hotel.
Stayed 1 night in Aug 2025

4/10 Poor

Gaston

Traveled with group
Liked: Cleanliness
Disliked: Staff & service, property conditions & facilities, room comfort
It’s very weird. I felt like I was breaking in a house
Stayed 1 night in Jul 2025

6/10 Okay

Travis

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
I hated that they're was absolutely know communication except through text. Have a question text. Need to ask something text. Building was nice but a little loud but not to bad. Just poor communication.
Stayed 1 night in Jul 2025

4/10 Poor

Stan

Traveled with family
Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service, room comfort

One star overall.

Place extremely difficult to locate. Took 15 minutes to locate upon arrival. No signs or labels anywhere. Bed small. Room small. Not enough for 2 adult males. Noise from people partying went on thru 5am.! Bar below room. Check in process rediculous. No live person at any time at all. No contact info beyond electronic. Checkout same. We already were gone by 2 hours when they requested checkout timeframe. Were texted to leave bedroom door open too late to do so. Neighborhood seems to be predominatly gay. We are NOT. Should be mentioned in advertising somewhere. Was unclear whether we were welcome to use common area or not. Place was clean. Showers/bathrooms nice
In town for Cubs game.
Stayed 1 night in Aug 2025

10/10 Excellent

Colin

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect for a night. Nice shared living space and 2 bathrooms. Didn’t have any issues or even see anyone else there
Stayed 1 night in Jul 2025

10/10 Excellent

Helen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again.
Stayed 5 nights in Jul 2025

6/10 Okay

Christopher

Traveled with family
Disliked: Staff & service, amenities, property conditions & facilities
Staff was nearly nonexistent. Arrived 20 minutes early. Texted owner and was told check in was 4:00, even though no one was there. Was told I could check in any time after 4:00, but wasn’t given access until 4:05. Room we stayed on was the 3rd floor. Room was very warm and could have used a ceiling fan. Breakfast was minimal and would have been a good chance to interact with the owner. Felt like owners wanted nothing to do with us.
Stayed 2 nights in Jul 2025

2/10 Terrible

Kenneth

No place to park
Stayed 1 night in Jul 2025

8/10 Good

Susan, South Bend

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
Loved the space - it was like a private apartment with a living room, kitchenette area, bathroom, bedroom. Was promised a parking pass, which was never delivered. The closeness to Wrigley Field and Southport area was fabulous. Be prepared for night noise from nearby establishments - the owners are quite upfront about that. I (we) would definitely stay here again.
Stayed 1 night in Jul 2025

10/10 Excellent

Jeremy

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Jul 2025

10/10 Excellent

Steve, Hopkins

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Above a pizza place with great specials offered and the decor was a mix of what looked like a different decor for each room
Stayed 1 night in Jul 2025

8/10 Good

TAMI, IOWA CITY

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was hard to find. The room was very small but clean.
Stayed 2 nights in Jul 2025

10/10 Excellent

Geoffrey

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Hit the lottery!

I had my scheduled accommodation bail on me last minute- it was a real bummer because it had parking and was close to Wrigley (my destination). Luckily, I found Dorothy's Place open and I reserved it. I found parking right around the corner, and it was really easy to get in and out and around the town. It is located in Boystown, which was a fun and safe vibe. I never felt endangered and the room was AWESOME. I had the suite with the bathroom- it was spacious, clean, and comfortable. It was like a 10 minute walk to Wrigley and all of the surrounding areas (I caught 3 games in my two nights!). I really felt like I had hit the lottery, not only because of the last-minute availability but because of the quality and the value. I would stay here in a flash if I were lucky enough to get back to the city!
Stayed 2 nights in Jul 2025

10/10 Excellent

Verified traveler

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

❤️❤️❤️

My bestie and I had a wonderful stay when we came for the Stray Kids concert! Cute room, free breakfast in the building next door, and room service from Big Gay Sal's Pizza downstairs! So good and so fun! Would love to come back!
Stayed 1 night in Jun 2025

8/10 Good

Jenny

Business traveler
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Jun 2025

10/10 Excellent

Lynn, Zionsville

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Near wrigley field
Stayed 1 night in Jun 2025

8/10 Good

Philip

Liked: Cleanliness, staff & service, property conditions & facilities
I enjoyed my stay.
Stayed 3 nights in Jun 2025

10/10 Excellent

Tanner

Stayed 1 night in Jun 2025

8/10 Good

Theodore

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The area has a lot of fun nightlife and things to do, but it was surprisingly quiet in our room! The room itself was clean and felt quite private, despite being in the shared suite. All the other guests we met were kind and courteous too! We drove, and parking was somewhat difficult but the map provided showing parking rules for surrounding roads made that much easier! The only thing we didn’t love was the provided breakfast, my partner told me they would have loved for some sausage or eggs to be included.
Stayed 2 nights in Jun 2025

10/10 Excellent

Alexis

Stayed 1 night in Jun 2025

10/10 Excellent

Joshua

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Great little spot with all you need. Clean, cozy and a great breakfast!
Stayed 1 night in May 2025

10/10 Excellent

Jose

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Super clean and close to transit for easy access to anywhere you need to go.
Stayed 3 nights in May 2025