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Dorothy's

2.0 star property
VIP Access

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Photo gallery for Dorothy's

Living area
Free WiFi, bed sheets
Living area
Mini-fridge, microwave, freezer, paper towels
Free daily continental breakfast

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen

Explore the area

View in a 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
VIP Access
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  • Expect exceptional service
  • Extra savings and perks for BONUS+ members
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Room options

View all photos for Basic Single Room

Free WiFi, bed sheets

Basic Single Room

9.0 out of 10
Wonderful
(4 reviews)
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
  • Free Wi-Fi

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

10.0 out of 10
Exceptional
(1 review)
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

7.0 out of 10
Good
(4 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
  • Free Wi-Fi

View all photos for City Single Room

Free WiFi, bed sheets

City Single Room

  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

9.8 out of 10
Exceptional
(6 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Basic Apartment

Free WiFi, bed sheets

Basic Apartment

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

View all photos for City Apartment

Free WiFi, bed sheets

City Apartment

  • 5 bedrooms
  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Single Sofa Bed
  • Free Wi-Fi

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About this property

Dorothy's

This smoke-free bed & breakfast features a microwave in a common area, a fridge in a common area and a TV in a common area. Free continental breakfast and free WiFi in public areas are also provided. Housekeeping is available on request.
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.
During your stay at Dorothy's, you're just a quick walk from Wrigley Field. You'll find features such as free breakfast and free WiFi in public areas.
  • Free continental breakfast served daily
  • Free Wi-Fi (speed: 25+ Mbps)
  • Amenities include a communal living room, TV in a common area and a shared microwave
  • Within a 15-minute walk of Wrigley Field and Lake Michigan
  • Pets welcome for a fee
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.

Guests are served a free continental breakfast daily from 6:00 AM to 10:00 AM.

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 at the property

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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property does not have a front desk. Prior to arrival, guests must complete online registration with the property via a secure link. Guests will be asked to provide the property with a copy of their government-issued photo ID before arrival. Guests arriving after 10:00 PM must make advance arrangements by contacting the property using the information on the booking confirmation. Guests planning to arrive outside of normal check-in hours will receive an email before arrival with check-in information and an access code. Guests can access their accommodation through a private entrance. A virtual front desk provides assistance to guests.

Property is also known as

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

Dorothy's Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 79 out of 140 reviews
Rating 8 - Good. 36 out of 140 reviews
Rating 6 - Okay. 10 out of 140 reviews
Rating 4 - Poor. 9 out of 140 reviews
Rating 2 - Terrible. 6 out of 140 reviews

9.0/10

Cleanliness

8.2/10

Staff & service

8.8/10

Amenities

8.8/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Winter Fox

Liked: Cleanliness, property conditions & facilities
cozy and close to cool places
Stayed 2 nights in Jan 2026
Verified

8/10 Good

Erica

Liked: Cleanliness, property conditions & facilities
Automated check-in worked well, waffles were great
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

ROMEO

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun place
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Yesim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was nicee
Stayed 2 nights in Jan 2026
Verified

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

10/10 Excellent

Zac

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice location to wrigleyville
Stayed 1 night in Sep 2025
Verified

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

10/10 Excellent

Maricel

Liked: Cleanliness, staff & service, property conditions & facilities
At first, I was scared because it has no front desk. However, you just have to follow the instructions and everything went well. It was truly a unique experienced.
Stayed 1 night in Mar 2026
Verified

8/10 Good

Philip

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

10/10 Excellent

David

Liked: Cleanliness, staff & service
All as promised
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I stayed here during a week of business etc and found the accommodations excellent for a long-ish stay. My room was the Purple Room - private bath, dining area, living room and separate bedroom. Clean, quiet, comfortable and appointed with everything one would need: Coffee maker, small fridge, microwave, dishes. Plenty of towels and storage in the bathroom. Big comfortable sectional sofa to lounge/work on. The staff is off site and responded quickly to text messages. The lock code provided easy and safe access to the room. VERY fun neighborhood - walking distance to everything, including Chicago's beautiful lakefront.
Stayed 6 nights in Mar 2026
Verified

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

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
Verified

10/10 Excellent

Daniel

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

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

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

8/10 Good

Lisa

Liked: Cleanliness, staff & service, property conditions & facilities
Halsted is a nice neibourhood. We liked the secondhand shops.
Stayed 3 nights in Oct 2025
Verified

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
Verified

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

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Quick overnight visit and 5th stay at this property. Everything on point as usual!
Stayed 1 night in Aug 2025
Verified

10/10 Excellent

Anthony

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

10/10 Excellent

Rae

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

Loved Dorothy’s!

Fun little place! Great location, lots of fun things to do nearby. Parking can be a bit funky, as with any city. But easy to find, easy to get into, very clean and staff was very helpful.
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very friendly and helpful staff. Rooms and bathrooms are very clean. I enjoyed my stay., it was cozy and comfortable. I would definitely stay at Dorothys again if I am back in the area.. I would also recommend it to friends meeting to stay near Wrigley or downtown.
Stayed 9 nights in Aug 2025
Verified

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
Verified

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