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Dorothy's

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

Choose dates to view prices

Photo gallery for Dorothy's

Free WiFi, bed sheets
Full-sized fridge, microwave, toaster oven, cookware/dishes/utensils
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Living area
A short walk from Wrigley Field, Dorothy's provides free continental breakfast, laundry facilities and more. Stay connected with free in-room WiFi.
VIP Access

Reviews

8.4 out of 10
Very good

Popular amenities

  • Breakfast included
  • Pet-friendly
  • Kitchen
  • Laundry
  • Air conditioning
  • Free WiFi
The current price is S$146
includes taxes & fees
29 Sept - 30 Sept

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Room options

Check availability for these dates

Tonight

Sep 23 - Sep 24
Check availability for tonight Sep 23 - Sep 24

Tomorrow

Sep 24 - Sep 25
Check availability for tomorrow Sep 24 - Sep 25
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 fridge/freezer
4 bedrooms
Detached private bathroom
Hairdryer
2 bathrooms
Microwave
  • 111 sq m
  • 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

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
5 bedrooms
Detached private bathroom
Hairdryer
3 bathrooms
Microwave
  • 5 bedrooms
  • 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 fridge/freezer
Hairdryer
2 bathrooms
Microwave
Shared/communal kitchen
Local meal delivery service
  • 4 sq m
  • Sleeps 2
  • 1 Double Bed

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

8.0 out of 10
Very good
(1 review)

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
Hairdryer
Private bathroom
Microwave
Shared/communal kitchen
Local meal delivery service
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Single Room

Free WiFi, bed sheets

Basic Single Room

9.0 out of 10
Wonderful
(4 reviews)

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
Hairdryer
2 bathrooms
Microwave
Shared/communal kitchen
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 fridge/freezer
Hairdryer
2 bathrooms
Microwave
Shared/communal kitchen
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 fridge/freezer
Hairdryer
2 bathrooms
Microwave
Shared/communal kitchen
Local meal delivery service
  • 5 sq m
  • Sleeps 2
  • 1 Queen Bed

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About the area

Map
3445 N Halsted St, Chicago, IL, 60657

What's nearby

  • Wrigley Field - 8 min walk - 0.7 km
  • Vic Theatre - 9 min walk - 0.8 km
  • Lincoln Park Zoo - 3 min drive - 3.2 km
  • Aragon Ballroom - 4 min drive - 3.5 km
  • Michigan Avenue - 6 min drive - 6.0 km

Getting around

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

Restaurants

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

About this property

Dorothy's

Bed & breakfast near Wrigley Field
Dorothy's provides amenities, such as free continental breakfast and laundry facilities. Guests can connect to free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • Smoke-free property, luggage storage and a TV in reception
  • Local meal delivery service
Room features
All guest rooms at Dorothy's have comforts, such as air conditioning, as well as
Extra amenities include:
  • Showers, hairdryers and soap
  • Communal kitchens, full-sized fridge/freezers and microwaves

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 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 lift

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 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 are 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.
Cots (infant beds) are not available

Payment types at the property

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)
  • Cleaning/housekeeping/linen 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 any lifts

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 does it cost to stay at Dorothy's?

As of 23 Sept, 2025, prices found for a 1-night stay for 2 adults at Dorothy's on 29 Sept, 2025 start from S$145.90, 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.

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?

Checkout 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 mile (2 km) of Lincoln Park, Wrigley Field and Lake Michigan. Vic Theatre and Advocate Illinois Masonic Medical Center are also within 15 minutes. 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. 41 out of 76 reviews
Rating 8 - Good. 17 out of 76 reviews
Rating 6 - Okay. 8 out of 76 reviews
Rating 4 - Poor. 5 out of 76 reviews
Rating 2 - Terrible. 5 out of 76 reviews

8.8/10

Cleanliness

7.6/10

Staff & service

8.6/10

Amenities

8.4/10

Property conditions & facilities

8.4/10

Eco-friendliness

Reviews

10/10 Excellent

Daniel

Liked: Cleanliness, amenities
Clean room beautiful.yards convenient
Stayed 2 nights in Aug 2025

8/10 Good

Philip

Liked: Cleanliness, staff & service, property conditions & facilities
I enjoyed my stay.
Stayed 3 nights in Jun 2025

10/10 Excellent

JOSE HUMBERTO CORRALES

Liked: Amenities
Simplemente nos encantó el lugar
Stayed 2 nights in May 2025

10/10 Excellent

Helen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again.
Stayed 5 nights in Jul 2025

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

Thomas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location to the Wrigley Field. That’s truly what we’re looking for. I did not realize that it was a communal bathroom, but I probably would’ve read what I was booking then I would’ve been aware of when I showed up.
Stayed 1 night in Jul 2025

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

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

10/10 Excellent

Colin

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect for a night. Nice shared living space and 2 bathrooms. Didn’t have any issues or even see anyone else there
Stayed 1 night in Jul 2025

10/10 Excellent

Verified traveller

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

Very Comfy

Super clean, quiet, comfortable place to stay. Will definitely be returning
Stayed 2 nights in May 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

Missy

Liked: Cleanliness, amenities, property conditions & facilities
I liked the little area it was in and how homey it felt, however the parking was a nightmare. You are given a parking pass, but it’s almost pointless if you can’t find a spot. After over an hour of trying to find parking, we still had to get up at 7am to find parking again since it was a tow zone at that time. When looking for help on what the signs meant (we are new to the area), the staff we messaged for help was passive-aggressive. If you ignore all that, then it was plenty fine.
Stayed 2 nights in Sep 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

Benjamin

Liked: Cleanliness, staff & service, property conditions & facilities
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 Excellent

Anthony

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

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

6/10 Okay

Travis

Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
I hated that they're was absolutely know communication except through text. Have a question text. Need to ask something text. Building was nice but a little loud but not to bad. Just poor communication.
Stayed 1 night in Jul 2025

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

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

10/10 Excellent

Raheem

Cool place
Stayed 1 night in Dec 2024

8/10 Good

Mike

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

10/10 Excellent

amanda

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

10/10 Excellent

Edgar Omar

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

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