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Dorothy's

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

Choose dates to view prices

Photo gallery for Dorothy's

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

Reviews

8.4 out of 10
Very good

Popular amenities

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

Explore the area

Map
3445 N Halsted St, Chicago, IL, 60657
  • Wrigley Field
    ‪8 min walk‬
  • Vic Theatre
    ‪9 min walk‬
  • Lincoln Park Zoo
    ‪3 min drive‬
  • Chicago, IL (ORD-O'Hare Intl.)
    ‪22 min drive‬
VIP Access
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  • Expect exceptional service
  • Extra savings and perks for Rewards members
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Room options

View all photos for Basic Apartment

5 bedrooms, free WiFi, bed sheets

Basic Apartment

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

View all photos for City Apartment

5 bedrooms, free WiFi, bed sheets

City Apartment

  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

View all photos for Standard Single Room

5 bedrooms, free WiFi, bed sheets

Standard Single Room

  • 48 sq ft
  • Sleeps 2
  • 1 Double Bed

View all photos for Standard Studio

5 bedrooms, free WiFi, bed sheets

Standard Studio

  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Single Room

5 bedrooms, free WiFi, bed sheets

Basic Single Room

  • 54 sq ft
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

5 bedrooms, free WiFi, bed sheets

City Single Room

  • 50 sq ft
  • Sleeps 2
  • 1 Queen Bed

View all photos for Economy Single Room

5 bedrooms, free WiFi, bed sheets

Economy Single Room

  • 50 sq ft
  • Sleeps 2
  • 1 Queen Bed

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About the neighborhood

Chicago

Located in Lakeview within a short walk of Wrigley Field, Dorothy's is within a mile (2 km) of other popular sights such as Lake Michigan. The 7 rooms at this 3-star bed & breakfast include refrigerators and microwaves and guests can enjoy free breakfast.
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 - 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 with free breakfast, a short walk to Wrigley Field
Guests of Dorothy's enjoy access to free WiFi in public areas, microwave in a common area, and refrigerator in a common area. If you plan to drive, free offsite parking is available. Friendly staff can provide luggage storage, and also offer advice about sightseeing. Additional amenities include laundry facilities, local meal delivery service, and a communal living room.
Guests can expect to find free WiFi. Other amenities include refrigerators, microwaves, and hair dryers. Housekeeping is available on request.

Languages

English

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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
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

  • This property welcomes pets for USD 25 per pet, per stay
  • Service animals exempt from fees

Property payment types

Important information

Optional extras

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

  • 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

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4:00 PM
  • Check-out: noon
  • Minimum check-in age: 18
Driving? This property offers free nearby parking.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards and debit cards. Cash is not accepted. 

Additional information about polices, regulations, and more:

  • There are no elevators.
  • No cribs or infant beds are available.
  • No rollaway or extra beds are available.

Property is also known as

Dorothy's Chicago
Dorothy's Bed & breakfast
Dorothy's Bed & breakfast Chicago

Frequently asked questions

What's there to do around Dorothy's?

This bed & breakfast is situated in Lakeview within a short 9-minute walk of Wrigley Field and also 16 minutes on foot from Lake Michigan. You'll also find Michigan Avenue and Chicago Riverwalk within a short drive.

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

As of Jun 15, 2025, prices found for a 1-night stay for 2 adults at Dorothy's on Jun 19, 2025 start from $97.0, excluding 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.

Is there parking available at Dorothy's?

No, there isn't parking at the bed & breakfast but you'll find free parking nearby.

Does Dorothy's feature a casino at the property?

No, Dorothy's doesn't have a casino.

Will I find an indoor pool at Dorothy's?

No, there is no indoor pool at this bed & breakfast.

Is Dorothy's good for couples?

Amenities at this bed u0026 breakfast that appeal to couples include a meal delivery service and free breakfast.

Does Dorothy's have a hot tub?

No, this bed & breakfast doesn't have a spa tub.

Does Dorothy's have a restaurant that serves breakfast?

Dorothy's offers free continental breakfast each morning though there is no restaurant.

Will Dorothy's allow pets to stay for free?

Although they can't stay for free, pets are welcome at Dorothy's for a fee of USD 25 per pet, per stay.

Are there connecting rooms at Dorothy's?

No, this bed & breakfast doesn't feature connecting guestrooms.

What is the closest airport to Dorothy's?

The closest major airport to Dorothy's is Chicago Midway Airport (MDW), which is 17.5 mi away (45 minutes by car). Another top airport is Chicago O'Hare Intl. Airport (ORD), which is located 16.6 mi away (48-minute drive).

Are there rooms with balconies that I can book at Dorothy's?

No, there aren't any guestrooms with balconies at Dorothy's.

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 Excellent

Keely

Traveled with partner
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

8/10 Good

Timothy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was clean, easy check-in. My only complaint is that wifi wasn't working.
Stayed 1 night in Mar 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

8/10 Good

Jaimee

Business traveler
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

Edgar Omar

Liked: Cleanliness, staff & service, property conditions & facilities
Nice
Stayed 5 nights in Jan 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

10/10 Excellent

Jayana

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 6 nights in Jan 2025

10/10 Excellent

Aberham

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

10/10 Excellent

amanda

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

10/10 Excellent

Raheem

Cool place
Stayed 1 night in Dec 2024

10/10 Excellent

Rajath

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Dec 2024

8/10 Good

shiju

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

10/10 Excellent

Nathaniel

Traveled with partner, Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
UwU
Stayed 1 night in Dec 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

Katrina

Liked: Cleanliness, property conditions & facilities
Stayed 2 nights in Dec 2024

8/10 Good

Mike

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good area, easy transportation
Stayed 3 nights in Dec 2024

10/10 Excellent

Shiva Kumar

Liked: Cleanliness
Stayed 3 nights in Dec 2024

10/10 Excellent

Gretel

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Dec 2024

10/10 Excellent

Sandra

Stayed 1 night in Nov 2024

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

10/10 Excellent

Rodrigo

Traveled with partner
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

vavondalyn

Traveled with family
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

2/10 Terrible

Evelyn

Traveled with partner
Disliked: Cleanliness, property conditions & facilities
En nada sale como está en las fotos o sea solo entré y con la misma me fui nunca me quedé ahí
Stayed 2 nights in Jan 2025

2/10 Terrible

GIANLUCA

Business traveler
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