See all properties
Save

Dorothy's

Property class: 2

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 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.
A bedroom with a bed, pillows, a painting, wall-mounted candelabras, and a window with curtains.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen
The current price is AU$209
includes taxes & fees
12 Oct - 13 Oct

Explore the area

View 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)
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

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
(2 reviews)
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

View all photos for City Single Room

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

City Single Room

  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

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

  • 111 sq m
  • 4 bedrooms
  • Sleeps 9
  • 2 Queen Beds, 2 Double Beds and 1 Single Sofa Bed

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 Single Sofa Bed

You may also like

Ad
Iron/ironing board, free WiFi, bed sheets

Motel 6 Suites Chicago Lisle IL

Lisle
  • Pet-friendly
  • Parking included
  • Free Wi-Fi
  • Air-conditioning
4.8 out of 10, 9 reviews
The price is AU$130
includes taxes & fees
25 Sept - 26 Sept
Motel 6 Suites Chicago Lisle IL

About the area

Chicago

At Dorothy's you'll be within just a 15-minute stroll of popular places like Wrigley Field and Lake Michigan. Highlights at this B&B include free continental breakfast. .This pet-friendly bed & breakfast offers free WiFi in public areas, luggage storage and a communal living room. Additionally, you'll find a microwave in a common area and a fridge in a common area. Each morning free breakfast is served. There's also the convenience of free parking nearby. .Attractions within a 10-minute drive of this Lakeview B&B include Michigan Avenue and Chicago Riverwalk.
View more B&B in ChicagoOpens in a new window

What's nearby

  • Lincoln Park - 8 min walk - 0.7 km
  • Wrigley Field - 8 min walk - 0.7 km
  • Vic Theatre - 11 min walk - 1.0 km
  • Wrigley View Rooftop - 13 min walk - 1.1 km
  • Theater Wit - 17 min walk - 1.5 km

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
  • ‪Replay Lakeview - ‬1 min walk
  • ‪Progress Bar Chicago - ‬2 min walk
  • ‪The Chicago Diner - ‬1 min walk

About this property

Dorothy's

Free breakfast is available daily. Public spaces have free WiFi. Dorothy's also features a communal living room, a microwave in a common area, and a fridge in a common area.

This Chicago bed & breakfast is smoke free.

  • 7 guestrooms or units
  • Continental breakfast (free)
  • Storage area for luggage
  • Television in lobby
  • No smoking on site
  • Microwave in a common area
  • Fridge in a common area
Dorothy's offers 7 air-conditioned accommodations, with a hairdryer. 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 a shower. Housekeeping is provided on request.

Similar properties

Lobby
The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
  • Pet-friendly
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
4.0 out of 5, Very good, 2,219 reviews
The price is AU$297
includes taxes & fees
13 Oct - 14 Oct
The Chicago Hotel Collection Ambassador Gold Coast

Property amenities

Internet

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

Parking and transport

  • Free offsite parking within 322 metres
  • 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 lift

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 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: USD 25 per pet, per stay
    • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Cots (infant beds) are not available.

Payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • 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)
  • Cleaning/housekeeping/linen fee: USD 5 per day

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property accepts Visa, Mastercard, American Express, Discover and debit cards. Cash is not accepted. For guests' safety, the property includes a fire extinguisher in all accommodation.

Property is also known as

Dorothy's Chicago

Dorothy's Bed & breakfast

Dorothy's Bed & breakfast Chicago

Frequently asked questions

Are there any beaches close to Dorothy's?

The closest beach to Dorothy's is Montrose Beach (2.6 km).

How much does it cost to stay at Dorothy's?

As of 12 Sept 2026, prices found for a 1-night stay for 2 adults at Dorothy's on 12 Oct 2026 start from AU$209, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does Dorothy's serve breakfast?

You bet, free continental breakfast is served daily from 6:00 AM to 10:00 AM.

Is there a free airport shuttle available at Dorothy's?

No, Dorothy's does not offer an airport shuttle service.

What time are check-in & check-out at Dorothy's?

Check-in begins at 4:00 PM. Check-out time is noon.

Dorothy's Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 105 out of 176 reviews
Rating 8 - Good. 40 out of 176 reviews
Rating 6 - Okay. 14 out of 176 reviews
Rating 4 - Poor. 11 out of 176 reviews
Rating 2 - Terrible. 6 out of 176 reviews

9.2/10

Cleanliness

8.4/10

Staff & service

8.8/10

Amenities

8.8/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Lynne

Liked: Cleanliness, property conditions & facilities
Great kitchy place. The stairs are a bit hard esprit lots of luggage, but the room was quaint and the property was clean
Stayed 2 nights in May 2026
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

8/10 Good

Gladys

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I stayed 4 nights, we liked the cleanliness, the location, the value and having the option of breakfast. My only concern was the room being very small and we had to share the bathroom. But in general it was a quiet good location.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely perfect stay in Chicago. Everything we needed was there, breakfast was over the top amazing. I LOVE the area and the pizza spot downstairs, this place includes other perks also like BOGO well drink downstairs. Big Gay Sal’s pizza also does room service. I have never felt so at home away from home. 10/10 recommend, HIGHLY recommend
Stayed 1 night in May 2026
Verified review

8/10 Good

Jia

Liked: Cleanliness
lots of clean rooms and clean bathrooms with products you can use. keep in mind however that not every room has its own private bathroom
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Adrian

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It is a shared experience. It helps to be respectful and polite to the other patrons
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I loved everything about this place! I was a bit skeptical when I saw how inexpensive it was relative to the location (a 5 min walk to Wrigley), but it was just perfect. A 100+ yr old house in the heart of Halsted, super clean, really quiet (weekday only stay), friendly people — it checked every box. I’ll never stay anywhere but here when I come to Chicago for Cubs games.
Stayed 1 night in May 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

8/10 Good

Heather

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It is a wonderful room with a comfortable bed and couch. It should be noted that the directions are complex for parking and just entering the building. Parking is extremely difficult to find. It is also a party district but we were there during the week and it was quiet. I absolutely adored the space though once settled.
Stayed 1 night in May 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

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

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

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

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

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

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

10/10 Excellent

Daniel

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

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

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

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