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Dorothy's

3.0 star property
Bed & breakfast with free breakfast, a short walk to Wrigley Field

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Photo gallery for Dorothy's

Relax in this stylish living area with a large sofa, glass coffee table, and patterned rug.
Bathroom features a shower with a glass door, a vanity with a mirror, and a toilet.
Classic design room with a bed, mirror, and lamp, offering a view of a nearby building.
Enjoy meals in the kitchen with a dining area and sink overlooking the view.
Relax in this open-plan living space with a dining area, featuring a sofa, chair, and dining table.

Popular amenities

  • Breakfast included
  • Pet friendly
  • Kitchen
  • Laundry
  • Air conditioning
  • Free WiFi

Room options

Available filters for rooms
Showing 7 of 7 rooms

View all photos for Basic Apartment

1 bedroom, free WiFi, bed sheets

Basic Apartment

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
4 bedrooms
2 bathrooms
Detached private bathroom
Hair dryer
Microwave
  • 111 sq m
  • Sleeps 9
  • 2 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

View all photos for City Apartment

1 bedroom, free WiFi, bed sheets

City Apartment

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
5 bedrooms
3 bathrooms
Detached private bathroom
Hair dryer
Microwave
  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

View all photos for Standard Single Room

1 bedroom, free WiFi, bed sheets

Standard Single Room

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Hair dryer
2 bathrooms
Microwave
Shared/communal kitchen
  • 4 sq m
  • Sleeps 2
  • 1 Double Bed

View all photos for Standard Studio

1 bedroom, free WiFi, bed sheets

Standard Studio

8.0 out of 10
Very good
(1 review)

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Hair dryer
Private bathroom
Microwave
Shared/communal kitchen
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Single Room

1 bedroom, free WiFi, bed sheets

Basic Single Room

8.8 out of 10
Excellent
(3 reviews)

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Hair dryer
2 bathrooms
Microwave
Shared/communal kitchen
  • 6.6 sq m
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

1 bedroom, free WiFi, bed sheets

City Single Room

10.0 out of 10
Exceptional
(1 review)

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Hair dryer
2 bathrooms
Microwave
Shared/communal kitchen
  • 5 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Economy Single Room

1 bedroom, free WiFi, bed sheets

Economy Single Room

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Hair dryer
2 bathrooms
Microwave
Shared/communal kitchen
  • 5 sq m
  • Sleeps 2
  • 1 Queen Bed

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About the neighborhood

Map
3445 N Halsted St, Chicago, IL, 60657

What's nearby

  • Wrigley Field - 8 min walk - 0.5 miles
  • Vic Theatre - 9 min walk - 0.5 miles
  • Lincoln Park Zoo - 3 min drive - 2.0 miles
  • Aragon Ballroom - 4 min drive - 2.2 miles
  • Michigan Avenue - 6 min drive - 3.7 miles

Getting around

  • Chicago Clybourn Station - 5 min drive
  • Addison Station (Red Line) - 7 min walk
  • Chicago Midway Airport (MDW) - 45 min drive

Restaurants

  • ‪Sidetrack - ‬2 min walk
  • ‪Roscoe's - ‬2 min walk
  • ‪Hydrate - ‬1 min walk
  • ‪Progress Bar Chicago - ‬2 min walk
  • ‪Replay Lakeview - ‬1 min walk

About this property

Dorothy's

Bed & breakfast near Wrigley Field
Dorothy's provides amenities like free continental breakfast and laundry facilities. Guests can connect to free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • A TV in the lobby, luggage storage, and smoke-free premises
  • Local meal delivery service
Room features
All guestrooms at Dorothy's boast comforts such as air conditioning, as well as amenities like free WiFi.
Extra amenities include:
  • Showers, hair dryers, and soap
  • Communal kitchens, full-sized refrigerators/freezers, and microwaves

Languages

English

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

Frequently asked questions

Is Dorothy's pet-friendly?

Yes, pets are allowed at this property. There's a fee of USD 25 per pet, per stay. Service animals are exempt from fees.

How much is parking at Dorothy's?

There is free parking nearby.

What time is check-in at Dorothy's?

Check-in start time: 4:00 PM; Check-in end time: 10:00 PM. A fee applies for early check-in (subject to availability).

What time is check-out at Dorothy's?

Check-out is at noon. Late check-out is available for a fee (subject to availability).

Where is Dorothy's located?

Located in Lakeview, this bed & breakfast is within 1 mi (2 km) of Lincoln Park, Wrigley Field, and Lake Michigan. Vic Theatre and Lincoln Hall are also within 2 mi (3 km). Addison Station (Red Line) is 7 minutes by foot and Belmont Station (Red Line) is 11 minutes.

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Dorothy's Reviews

Reviews

8.4

Very Good

Rating 10 - Excellent. 30 out of 55 reviews
Rating 8 - Good. 14 out of 55 reviews
Rating 6 - Okay. 6 out of 55 reviews
Rating 4 - Poor. 0 out of 55 reviews
Rating 2 - Terrible. 5 out of 55 reviews

9.0/10

Cleanliness

8.0/10

Staff & service

8.4/10

Amenities

8.6/10

Property conditions & facilities

8.6/10

Eco-friendliness

Reviews

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

10/10 Excellent

Steve

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

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

8/10 Good

Susan

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

Lynn

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

10/10 Excellent

Keely

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!
Stayed 1 night in Nov 2024

10/10 Excellent

Anthony

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

8/10 Good

Theodore

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

8/10 Good

Jaimee

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

Would recommend to stay again

Was having surgery but was canceled so I didn’t get to stay very long but would definitely stay again
Stayed 4 nights in Jan 2025

10/10 Excellent

Raheem

Cool place
Stayed 1 night in Dec 2024

10/10 Excellent

Aberham

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
How nice it was and how close it was
Stayed 2 nights in Jan 2025

2/10 Terrible

Lakshmikant

Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
The street was always very noisy
Stayed 4 nights in Mar 2025

10/10 Excellent

Rodrigo

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quaint, convenient, and extremely friendly. Recommending it to all my friends traveling to Chicago.
Stayed 2 nights in Nov 2024

8/10 Good

Douglas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I was charged twice for one hotel night
Stayed 1 night in May 2025

10/10 Excellent

amanda

Liked: Property conditions & facilities
Great
Stayed 3 nights in Jan 2025

8/10 Good

antoinette lewis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was clean and spacious. It looked just like the pictures online. The other roomies in the house were nice and clean. My bed was very comfortable including plush pillows.A little unorthodox their entry and breakfast but it all worked out. I look forward to staying there again in the future. The price was a major steal.♥️😊
Stayed 2 nights in Mar 2025

2/10 Terrible

Larry

Liked: Property conditions & facilities
Disliked: Staff & service, room comfort
just a room no private bath
Stayed 1 night in Jan 2025

8/10 Good

vavondalyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was nice, I didn't know how to adjust the heat in the room, other than that I will stay again.
Stayed 1 night in Nov 2024

6/10 Okay

Frank

Disliked: Staff & service, property conditions & facilities

Dissatisfied with our stay

Dissatisfied with our stay!! Our experience was less desirable than expected. Normal and customary check in time is 3pm, we couldn’t check in until 4 without added cost. This is in a predominantly LGBT neighborhood, not mentioned. The “quirky” old building was just not maintained well, so in disrepair rather than quirky. Mold around the shower floor. Tiny room with shared bathroom, not mentioned in description. The distance to Wrigley Field was only about a ten minute walk, which was great!
Stayed 2 nights in Apr 2025

6/10 Okay

Wendy

Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
Parking is difficult. Closest designated spot was 2 blocks away. Booking was easy enough but communication between site and accommodation was inefficient. Email was not passed on for final access instructions to unmanned accommodation site. The finalisation process did not allow for visitors with International phone numbers to be contacted directly either. Login does not accept driver's licence picture.
Stayed 1 night in Apr 2025

8/10 Good

shiju

Liked: Amenities
No staff to assist. Room is clean and well. Parking is confusing. Breakfast is fine.
Stayed 2 nights in Dec 2024

6/10 Okay

Zachary

Disliked: Staff & service
The property itself is in a great location and offers good value for the price. However, the experience was unfortunately overshadowed by poor customer service. Upon booking, we received multiple links with different sets of information—one with property details, another with check-in instructions, and other links as well. Assuming there was a master link as the webpage seemed to suggest, we missed the one specifically for check-in. When we arrived just after 4pm on 04/17, we used the keypad to contact the property for assistance. The woman who answered the call was unnecessarily rude and dismissive—something that could have been avoided with a simple, helpful response. A little courtesy goes a long way, especially in hospitality. The stay itself was fine, but the unprofessional attitude of certain staff members left a lasting negative impression. With better communication and a more respectful approach to guests, this property could truly stand out.
Stayed 1 night in Apr 2025

6/10 Okay

Otis

Liked: Cleanliness, property conditions & facilities, room comfort

Comfy Stay but Bad Entry !!

Entry was a bit of a challenge. I did not get the information needed to get in until after I was there and it was freezing. The directions in the app were not explicit bough about the process or where and how you filled out this pre evaluation… there were multiple links you had to follow to find the code to get in. I had no service for some reason, once up stairs in my room I couldn’t find the WiFi access and I had to go back outside to find WiFi at the 7 eleven in order to follow a link to find the password. The next morning I texted what time and where breakfast was and I was told to follow the link. Pretty unproductive considering they texted back.
Stayed 2 nights in Dec 2024

2/10 Terrible

GIANLUCA

Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
This was one of the worst experiences I’ve ever had with a B&B. When I called for location instructions, the staff couldn’t have cared less. Their only response was, “Just put the address,” with zero effort to actually help. To make matters worse, I had a work van and had to park on public streets because they don’t offer proper parking. I formally requested a refund for the inconvenience since I couldn’t leave my work materials unattended, and they rudely refused without any consideration. This place is a joke—they only care about taking your money and provide absolutely no customer service. If you’re looking for a place to stay that values guests, stay FAR away from Dorothy’s. They don’t deserve anyone’s business.
Stayed 1 night in Dec 2024

6/10 Okay

Christopher

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