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Dorothy's

2.0 star property

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Photo gallery for Dorothy's

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.
A kitchen with a dining table set for a meal, a dog sitting at the table, and various kitchen appliances and utensils.
A bedroom with a bed, pillows, a painting, wall-mounted candelabras, and a window with curtains.
A living room with a black patterned rug, a glass coffee table, a wooden dining table with chairs, a small bench, and a cityscape painting on the wall.
A modern kitchen with wooden cabinets, a stainless steel dishwasher, a coffee maker, and a glass dining table with chairs.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Kitchen
The current price is $124
$111 nightly
$124 total
Total with taxes and fees
Aug 10 - Aug 11

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
    ‪11 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪32 min drive‬

Room options

View all photos for Basic Single Room

A bedroom with a bed, green and red pillows, a painting on the wall, and a window with curtains.

Basic Single Room

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

View all photos for Economy Single Room

A bedroom with a wooden door, a bed with blue bedding, two framed artworks on the wall, and a small bedside table.

Economy Single Room

10.0 out of 10
Exceptional
(1 review)
  • 50 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Standard Single Room

A bedroom with a bed, a ceiling fan, and three framed pictures on the wall.

Standard Single Room

7.8 out of 10
Good
(6 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
  • Free WiFi

View all photos for City Single Room

A bedroom with a bed, a window, a painting, and a nightstand.

City Single Room

  • 50 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Standard Studio

A bedroom with a bed, a nightstand, a lamp, a wall-mounted picture, and a wall sconce.

Standard Studio

9.8 out of 10
Exceptional
(7 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Basic Apartment

A bedroom with a wooden door, a bed with blue bedding, two framed artworks on the wall, and a small bedside table.

Basic Apartment

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

View all photos for City Apartment

A bedroom with a wooden door, a bed with blue bedding, two framed artworks on the wall, and a small bedside table.

City Apartment

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

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The price is $119
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About the neighborhood

Chicago

Located in Chicago (Lakeview), Dorothy's is within a 15-minute walk of Wrigley Field and Lake Michigan. .This bed & breakfast is 3.6 mi (5.7 km) from Michigan Avenue and 4.4 mi (7 km) from Chicago Riverwalk.
View more B&B in ChicagoOpens in a new window

What's nearby

  • Lincoln Park - 8 min walk - 0.5 miles
  • Wrigley Field - 8 min walk - 0.5 miles
  • Vic Theatre - 11 min walk - 0.6 miles
  • Wrigley View Rooftop - 13 min walk - 0.7 miles
  • Theater Wit - 17 min walk - 1.0 mile

Getting around

  • Chicago Ravenswood Station - 5 min drive
  • Addison Station (Red Line) - 7 min walk
  • Chicago Midway Airport (MDW) - 48 min drive

Restaurants

  • ‪Sidetrack - ‬3 min walk
  • ‪Roscoe's - ‬2 min walk
  • ‪Hydrate - ‬1 min walk
  • ‪Replay Lakeview - ‬1 min walk
  • ‪The Chicago Diner - ‬1 min walk

About this property

Dorothy's

Dorothy's offers 7 air-conditioned accommodations with hair dryers. This Chicago bed & breakfast provides complimentary wireless Internet access, with a speed of 25+ Mbps. Guests can make use of the shared/communal kitchen. Bathrooms include showers. Housekeeping is provided on request.
Make yourself at home in one of the 7 air-conditioned rooms featuring microwaves. Prepare your meals in the shared/communal kitchen. Complimentary wireless internet access is available to keep you connected. Bathrooms have showers and hair dryers.
Make use of convenient amenities, which include complimentary wireless internet access and a communal living room.
A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Featured amenities include luggage storage, microwave in a common area, and refrigerator in a common area.
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 microwave
  • Mini-fridge

Conveniences

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

Guest services

  • Housekeeping (on request) (for a fee)

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

  • Freezer
  • Meal delivery service
  • Microwave
  • Mini-fridge
  • Paper towels
  • Restaurant dining guides
  • Shared kitchen access

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
Information provided by the property may be translated using automated translation tools

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
Safety features at this property include a fire extinguisher

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

8.6

Excellent

Rating 10 - Excellent. 101 out of 168 reviews
Rating 8 - Good. 38 out of 168 reviews
Rating 6 - Okay. 13 out of 168 reviews
Rating 4 - Poor. 10 out of 168 reviews
Rating 2 - Terrible. 6 out of 168 reviews

9.2/10

Cleanliness

8.4/10

Staff & service

9.0/10

Amenities

8.8/10

Property conditions & facilities

Reviews

Verified review

8/10 Good

stan

Liked: Cleanliness, amenities, property conditions & facilities
Inexpensive place for Chicago.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Kimberly

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the place. Has everything I needed.
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Winter Fox

Liked: Cleanliness, property conditions & facilities
cozy and close to cool places
Stayed 2 nights in Jan 2026
Verified review

8/10 Good

Erica

Liked: Cleanliness, property conditions & facilities
Automated check-in worked well, waffles were great
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

ROMEO

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun place
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
First time at Dorothy's but I've stayed at her sister location so I know the owner/management and what to expect. Great location and the building is kept up very well. My only non happy comment was no dresser in this room. Its ok since this visit was just me. Being able to use a full kitchen and store food in the refrigerator is a major plus
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Yesim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was nicee
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

Ashley

Liked: Cleanliness, property conditions & facilities
Can’t beat the price or location. Everything seemed clean and I loved the waffles.
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Zac

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice location to wrigleyville
Stayed 1 night in Sep 2025
Verified review

8/10 Good

Philip

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

10/10 Excellent

James

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
What an absolutely amazing room, made me feel like home. Wonderful apartment in the middle of everything.
Stayed 1 night in Dec 2025
Verified review

10/10 Excellent

bijan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
so convenient, cozy, and welcoming. excellent
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Maricel

Liked: Cleanliness, staff & service, property conditions & facilities
At first, I was scared because it has no front desk. However, you just have to follow the instructions and everything went well. It was truly a unique experienced.
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Daniel

Liked: Cleanliness, amenities
Clean room beautiful.yards convenient
Stayed 2 nights in Aug 2025
Verified review

8/10 Good

Sam

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I would stay here again. Check-in comes with very detailed instructions, and it was a breeze– easy, straightforward. The unit was kept exceptionally clean, the kitchen is pretty well-stocked for anything you might want to make, the breakfast is a great way to start each day on time, and the availability of a parking permit is wonderful. The proximity to the best bars is unmatched, and you’re on the third floor, so the street noise isn’t even that bad. My only negative marks are that there are only two bathrooms for what could be up to 8 people, the water pressure is not great, and for some reason, the climate control was set to “Fire & Brimestone” for the duration of our stay, so we had to keep the window open. Otherwise, all top marks.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Trevor

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was great for a stay in Boystown
Stayed 1 night in Mar 2025
Verified review

8/10 Good

Konrad

Liked: Cleanliness, staff & service, amenities
It's a charming older house, with breakfast available in the morning (cereal, coffee, waffle machine). Not a bad location, plenty of bus stops nearby. Mention you're staying upstairs at Big Gay Sal's and get a discount.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

David

Liked: Cleanliness, staff & service
All as promised
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Joshua

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
Verified review

10/10 Excellent

Anthony

Love the coziness of the location and th area is nice and safe
Stayed 2 nights in Dec 2024
Verified review

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
Verified review

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I stayed here during a week of business etc and found the accommodations excellent for a long-ish stay. My room was the Purple Room - private bath, dining area, living room and separate bedroom. Clean, quiet, comfortable and appointed with everything one would need: Coffee maker, small fridge, microwave, dishes. Plenty of towels and storage in the bathroom. Big comfortable sectional sofa to lounge/work on. The staff is off site and responded quickly to text messages. The lock code provided easy and safe access to the room. VERY fun neighborhood - walking distance to everything, including Chicago's beautiful lakefront.
Stayed 6 nights in Mar 2026
Verified review

10/10 Excellent

Jose

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
Verified review

8/10 Good

Lisa

Liked: Cleanliness, staff & service, property conditions & facilities
Halsted is a nice neibourhood. We liked the secondhand shops.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Quick overnight visit and 5th stay at this property. Everything on point as usual!
Stayed 1 night in Aug 2025