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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
Free daily continental breakfast
Living area
Shower, hair dryer, towels, soap

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
  • Smoke-free property

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. 76 out of 135 reviews
Rating 8 - Good. 35 out of 135 reviews
Rating 6 - Okay. 9 out of 135 reviews
Rating 4 - Poor. 9 out of 135 reviews
Rating 2 - Terrible. 6 out of 135 reviews

9.0/10

Cleanliness

8.2/10

Staff & service

8.8/10

Amenities

8.6/10

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

Yesim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was nicee
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

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

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

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

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

David

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

Philip

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

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

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

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

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

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

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

Jennifer

Liked: Cleanliness, amenities, property conditions & facilities
Fantastic location within walking distance of Wrigley Field and many Lakeview hot spots. Check-in and check-out were seamless, and I was pleasantly surprised by the amount of space within the suite! It's definitely not for folks who aren't used to urban street noise, although it didn't bother me at all. My ONLY "complaint" was that the room was super cold. There is a portable radiator in the living room, but even turned up all the way, it didn't warm the space up at all. I located an extra blanket in the front closet, wrapped up in that, and was warm and happy as a clam. I will definitely be returning!
Stayed 1 night in Jan 2026
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

2/10 Terrible

Kathy

Disliked: Cleanliness, amenities, property conditions & facilities
Absolutely disgusting
Stayed 1 night in Nov 2025