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Dorothy's

2.0 star property

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Photo gallery for Dorothy's

Living area
Living area
Free WiFi, bed sheets
Shower, hair dryer, towels, soap
Free daily continental breakfast

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Kitchen
The current price is $115
includes taxes & fees
May 26 - May 27

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

Free WiFi, bed sheets

Basic Single Room

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

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

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

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

7.0 out of 10
Good
(4 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

Free WiFi, bed sheets

City Single Room

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

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

9.8 out of 10
Exceptional
(6 reviews)
  • 1 bedroom
  • 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

B&B in Lakeview
This smoke-free bed & breakfast features a microwave in a common area, a refrigerator in a common area, and a TV in a common area. Free continental breakfast and free WiFi in public areas are also provided. Housekeeping is available on request.
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.
Guests can enjoy a complimentary breakfast each morning. Wireless Internet access is complimentary. This Chicago bed & breakfast also offers a communal living room, a microwave in a common area, and a refrigerator 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 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. 74 out of 125 reviews
Rating 8 - Good. 30 out of 125 reviews
Rating 6 - Okay. 8 out of 125 reviews
Rating 4 - Poor. 7 out of 125 reviews
Rating 2 - Terrible. 6 out of 125 reviews

9.0/10

Cleanliness

8.2/10

Staff & service

8.8/10

Amenities

8.6/10

Property conditions & facilities

Reviews

10/10 Excellent

David

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

10/10 Excellent

Jace

Stayed 1 night in Jan 2026

10/10 Excellent

Jennifer

Liked: Cleanliness, amenities, property conditions & facilities
Fantastic location within walking distance of Wrigley Field and many Lakeview hot spots. Check-in and check-out were seamless, and I was pleasantly surprised by the amount of space within the suite! It's definitely not for folks who aren't used to urban street noise, although it didn't bother me at all. My ONLY "complaint" was that the room was super cold. There is a portable radiator in the living room, but even turned up all the way, it didn't warm the space up at all. I located an extra blanket in the front closet, wrapped up in that, and was warm and happy as a clam. I will definitely be returning!
Stayed 1 night in Jan 2026

10/10 Excellent

Winter Fox, Shasta Lake

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

8/10 Good

Erica

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

10/10 Excellent

Yesim

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

10/10 Excellent

Mark

Liked: Cleanliness, amenities, property conditions & facilities
The room was small, but very comfortable. Initially, I was a bit leery of the "no reception; we'll send you a code" check-in, but it went very smoothly. The code worked on all the doors it was supposed to work on, and I appreciated the triple-layer of code security - outside door, door to the floor, door to the room. Dorothy's is ideally situated, and easy walking distance to attractions in the area, in addition to the Red line train and numerous bus lines. If I had to ding Dorothy's on anything, it's this: Coffeemate isn't cream and doesn't do the same in your coffee in the morning as does half-and-half.
Stayed 3 nights in Dec 2025

8/10 Good

Janne

Stayed 4 nights in Dec 2025

10/10 Excellent

lashonte

Stayed 2 nights in Dec 2025

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

8/10 Good

David

Stayed 1 night in Dec 2025

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

10/10 Excellent

bijan

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

2/10 Terrible

Kathy

Traveled with family and small children
Disliked: Cleanliness, amenities, property conditions & facilities
Absolutely disgusting
Stayed 1 night in Nov 2025

10/10 Excellent

ROMEO

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun place
Stayed 3 nights in Nov 2025

8/10 Good

Sean

Liked: Cleanliness, staff & service, amenities
Arrangement was just a bit odd but the room was clean and secure and the location can't be beat. My room light had a flickering bulb and the fan was too unstable to use, but everything else was acceptable. One of the showers also had pretty bad water pressure but there's 2 available showers so that wasn't a problem the 2nd time.
Stayed 1 night in Nov 2025

4/10 Poor

John

Disliked: Cleanliness
There was a little bit of trash left over from the last guest. In addition, the fire alarm went off before checkout. I believe the owner was trying to wake me up. There was a smart type fire alarm that you can set off with your phone.
Stayed 1 night in Nov 2025

10/10 Excellent

Fernando Emmanuel

Liked: Cleanliness, staff & service, property conditions & facilities
Just breakfast no good… noise but I was advised, everything else is perfect!
Stayed 4 nights in Nov 2025

8/10 Good

Doug

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Shower water was cool so I expedited a clean up only.
Stayed 1 night in Oct 2025

10/10 Excellent

Zac

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

10/10 Excellent

Vincient, KANSAS CITY

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
If you're looking for something in Boys Town you could not ask for anything better, but with that comes challenges and parking and noise. There really is not parking provided but there is a parking permit available and then good luck finding parking anywhere nearby. It is a very nice facility and super clean. I thought the automated notices were a little gruff and not needed in the way they were written however they were very helpful and were very clear on the expectations. I would definitely stay here again, Even with the parking situation.
Stayed 2 nights in Oct 2025

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

8/10 Good

Steve

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Incredibly pleased with rooms/suite. Disappointed in having a cold shower and my husband skipped his. I have been informed that the water issue had been resolved this morning.
Stayed 1 night in Oct 2025

8/10 Good

Lisa

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

4/10 Poor

Troy

Disliked: Cleanliness, property conditions & facilities
Leaking water everywhere in bathroom, super old gross towels, super old sheets and blankets that may or may not have been clean and washed, carpet on stairs 85 years old and not vacuumed, no working outlet to charge anything, felt like motel 6.
Stayed 1 night in Oct 2025