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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

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

Reviews

8.4 out of 10
Very good

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

Free WiFi, bed sheets

Basic Apartment

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
4 bedrooms
Hair dryer
Detached private bathroom
2 bathrooms
Microwave
  • 111 sq m
  • 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

Highlights

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

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
2 bathrooms
Hair dryer
Microwave
Cookware/dishes/utensils
Local meal delivery service
  • 4 sq m
  • Sleeps 2
  • 1 Double Bed

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Private bathroom
Hair dryer
Microwave
Cookware/dishes/utensils
Local meal delivery service
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Single Room

Free WiFi, bed sheets

Basic Single Room

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
2 bathrooms
Hair dryer
Microwave
Cookware/dishes/utensils
Local meal delivery service
  • 5 sq m
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

Free WiFi, bed sheets

City Single Room

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
2 bathrooms
Hair dryer
Microwave
Cookware/dishes/utensils
Local meal delivery service
  • 5 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
2 bathrooms
Hair dryer
Microwave
Cookware/dishes/utensils
Local meal delivery service
  • 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

  • Lincoln Park - 8 min walk - 0.5 miles
  • 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
  • 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:
  • Luggage storage, local meal delivery service, and a TV in the lobby
  • Smoke-free premises
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
  • 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
  • Smoke-free property

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
Minimum check-in age: 18

Check-out

Check-out before noon

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 with special 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
  • 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.

What time is check-out at Dorothy's?

Check-out is at noon.

Where is Dorothy's located?

Located in Lakeview, this bed & breakfast is within a 10-minute walk of Briar Street Theatre and Wrigley Field. Lake Michigan is 0.8 mi (1.3 km) away. 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. 24 out of 41 reviews
Rating 8 - Good. 8 out of 41 reviews
Rating 6 - Okay. 5 out of 41 reviews
Rating 4 - Poor. 0 out of 41 reviews
Rating 2 - Terrible. 4 out of 41 reviews

8.8/10

Cleanliness

7.8/10

Staff & service

8.4/10

Amenities

8.6/10

Property conditions & facilities

8.6/10

Eco-friendliness

Reviews

10/10

Great little spot with all you need. Clean, cozy and a great breakfast!
Stayed 1 night in May 2025

10/10

Great location. Super clean and close to transit for easy access to anywhere you need to go.
Stayed 3 nights in May 2025

10/10

I initially came up to Chicago from Indiana and had found this place to stay for my duration. The area was lovely, arrangements were excellent and I loved the cottage feel to the Bed N’ Breakfast next door. If I’m ever in Chicago for another concert or to see more of the place, I’m coming back to Dorothy’s.
Stayed 1 night in May 2025

10/10

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

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

8/10

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

Cool place
Stayed 1 night in Dec 2024

8/10

The property was clean, easy check-in. My only complaint is that wifi wasn't working.
Stayed 1 night in Mar 2025

10/10

How nice it was and how close it was
Stayed 2 nights in Jan 2025

2/10

The street was always very noisy
Stayed 4 nights in Mar 2025

8/10

I was charged twice for one hotel night
Stayed 1 night in May 2025

10/10

Nice
Stayed 5 nights in Jan 2025

10/10

Quaint, convenient, and extremely friendly. Recommending it to all my friends traveling to Chicago.
Stayed 2 nights in Nov 2024

10/10

Great
Stayed 3 nights in Jan 2025

8/10

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

just a room no private bath
Stayed 1 night in Jan 2025

6/10

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

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

8/10

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

6/10

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

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

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

10/10

Stayed 1 night in May 2025

10/10

Simplemente nos encantó el lugar
Stayed 2 nights in May 2025

10/10

It was great for a stay in Boystown
Stayed 1 night in Mar 2025