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Dorothy's

3.0 star property

Photo gallery for Dorothy's

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

Reviews

8.4 out of 10
Very good

Popular amenities

  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning
  • Laundry room
  • Kitchen
The current price is AU$138
includes taxes & fees
19 Mar - 20 Mar

Explore the area

View map
3445 N Halsted St, Chicago, IL, 60657
  • Place, Lincoln Park
    ‪8 min walk‬
  • Place, Wrigley Field
    ‪8 min walk‬
  • Place, Vic Theatre
    ‪9 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪23 min drive‬

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

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

Free WiFi, bed sheets

City Single Room

  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

9.6 out of 10
Exceptional
(4 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

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

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About the area

Chicago

At Dorothy's you'll be within just a 15-minute stroll of popular places like Wrigley Field and Lake Michigan. Highlights at this B&B include free continental breakfast. .This pet-friendly bed & breakfast offers free WiFi in public areas, luggage storage and a communal living room. Other amenities include laundry facilities, a microwave in a common area and a fridge in a common area. Each morning free breakfast is served. There's also the convenience of free parking nearby. .Attractions within a 10-minute drive of this 3-property class Lakeview B&B include Michigan Avenue and Chicago Riverwalk.
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What's nearby

  • Lincoln Park - 8 min walk - 0.7 km
  • Wrigley Field - 8 min walk - 0.7 km
  • Vic Theatre - 9 min walk - 0.8 km
  • Anshe Emet Synagogue - 9 min walk - 0.8 km
  • Theater Wit - 16 min walk - 1.4 km

Getting around

  • Chicago Ravenswood Station - 5 min drive
  • Addison Station (Red Line) - 7 min walk
  • Chicago Midway Airport (MDW) - 48 min drive

Restaurants

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

About this property

Dorothy's

Free breakfast is available daily. Public spaces have free WiFi. Dorothy's also features laundry facilities, a communal living room, and a microwave in a common area.

This 3-star Chicago bed & breakfast is smoke free.

  • 7 guestrooms or units
  • Continental breakfast (free)
  • Self-service laundry
  • Storage area for luggage
  • Television in lobby
  • No smoking on site
  • Microwave in a common area
  • Fridge in a common area
Dorothy's offers 7 air-conditioned accommodations with shared/communal kitchens and a hairdryer. Guests can make use of the in-room full-sized fridge/freezers and microwaves.

Bathrooms include a shower. This Chicago bed & breakfast provides complimentary wireless Internet access, with a speed of 25+ Mbps. Housekeeping is provided on request.

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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) (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

  • 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
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

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

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property accepts Visa, Mastercard, American Express, Discover and debit cards. Cash is not accepted. For guests' safety, the property includes a fire extinguisher in all accommodation.

Property is also known as

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

Frequently asked questions

Are there any beaches close to Dorothy's?

The closest beach to Dorothy's is Montrose Beach (2.6 km).

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

As of 11 Mar 2026, prices found for a 1-night stay for 2 adults at Dorothy's on 19 Mar 2026 start from AU$138, 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.

Does Dorothy's serve breakfast?

You bet, free continental breakfast is served daily from 6:00 AM to 10:00 AM.

Is there a free airport shuttle available at Dorothy's?

No, Dorothy's does not offer an airport shuttle service.

What time are check-in & check-out at Dorothy's?

Check-in begins at 4:00 PM. Check-out time is noon.

Dorothy's Reviews

Reviews

8.4

Very good

Rating 10 - Excellent. 61 out of 109 reviews
Rating 8 - Good. 27 out of 109 reviews
Rating 6 - Okay. 8 out of 109 reviews
Rating 4 - Poor. 7 out of 109 reviews
Rating 2 - Terrible. 6 out of 109 reviews

8.8/10

Cleanliness

8.0/10

Staff & service

8.6/10

Amenities

8.6/10

Property conditions & facilities

Reviews

8/10 Good

David

Stayed 1 night in Dec 2025

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

10/10 Excellent

bijan

Travelled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
so convenient, cozy, and welcoming. excellent
Stayed 3 nights in Nov 2025

2/10 Terrible

Kathy

Travelled with family and small children
Disliked: Cleanliness, amenities, property conditions & facilities
Absolutely disgusting
Stayed 1 night in Nov 2025

10/10 Excellent

ROMEO

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

8/10 Good

Sean

Liked: Cleanliness, staff & service, amenities
Arrangement was just a bit odd but the room was clean and secure and the location can't be beat. My room light had a flickering bulb and the fan was too unstable to use, but everything else was acceptable. One of the showers also had pretty bad water pressure but there's 2 available showers so that wasn't a problem the 2nd time.
Stayed 1 night in Nov 2025

4/10 Poor

John

Disliked: Cleanliness
There was a little bit of trash left over from the last guest. In addition, the fire alarm went off before checkout. I believe the owner was trying to wake me up. There was a smart type fire alarm that you can set off with your phone.
Stayed 1 night in Nov 2025

10/10 Excellent

Fernando Emmanuel

Liked: Cleanliness, staff & service, property conditions & facilities
Just breakfast no good… noise but I was advised, everything else is perfect!
Stayed 4 nights in Nov 2025

8/10 Good

Doug

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Shower water was cool so I expedited a clean up only.
Stayed 1 night in Oct 2025

10/10 Excellent

Zac

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

10/10 Excellent

Vincient, KANSAS CITY

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
If you're looking for something in Boys Town you could not ask for anything better, but with that comes challenges and parking and noise. There really is not parking provided but there is a parking permit available and then good luck finding parking anywhere nearby. It is a very nice facility and super clean. I thought the automated notices were a little gruff and not needed in the way they were written however they were very helpful and were very clear on the expectations. I would definitely stay here again, Even with the parking situation.
Stayed 2 nights in Oct 2025

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

8/10 Good

Steve

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Incredibly pleased with rooms/suite. Disappointed in having a cold shower and my husband skipped his. I have been informed that the water issue had been resolved this morning.
Stayed 1 night in Oct 2025

8/10 Good

Lisa

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

4/10 Poor

Troy

Disliked: Cleanliness, property conditions & facilities
Leaking water everywhere in bathroom, super old gross towels, super old sheets and blankets that may or may not have been clean and washed, carpet on stairs 85 years old and not vacuumed, no working outlet to charge anything, felt like motel 6.
Stayed 1 night in Oct 2025

10/10 Excellent

Thomas

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Oct 2025

8/10 Good

Joshua

Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Proviso: You shouldn't stay here if you need accessibility options. However, it's a charming building and the rooms were pleasant. We didn't really interact with anyone - most of the check in was automated. Expect a basic, simple stay with a breakfast pantry that refreshes every couple of days.
Stayed 4 nights in Aug 2025

10/10 Excellent

Brian

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

10/10 Excellent

Gina

Travelled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exactly what I needed. Just in town for one night to see a late show at the Metro. Everything was walking distance. Adorable furnishings, clean, pet friendly, great breakfast and patio at the sister accommodation next door and well priced. Loud bars close by, but, that was as described. My dog was not bothered. Thank you!
Stayed 1 night in Sep 2025

10/10 Excellent

Donovan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 2 nights in Sep 2025

10/10 Excellent

Fabiola

Stayed 2 nights in Aug 2025

8/10 Good

Missy

Travelled with partner
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

10/10 Excellent

Kenneth

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Cute little place with good vibes, in a great location! Will definitely stay again! The only issue I really had during my stay was that I ordered drinks using the room service feature, they charged my card but never brought the drinks. The owner did not seem too concerned or willing to look into it much when I brought it to his attention. Mostly friendly, but felt like maybe he was wanting to rush me out of there. We had booked a late check out as well, which we paid extra for. Housekeeping came into the room without knocking or anything, two hours before check out time. Was not a big deal but should have knocked. These are things that I am able to overlook, would still stay again!
Stayed 3 nights in Sep 2025

8/10 Good

Mark

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

4/10 Poor

Justin

Disliked: Cleanliness, staff & service, room comfort

Cheap hostel, fine if that’s your jam

THIS IS NOT A HOTEL. It’s not even a “Bed and Breakfast.” It’s a hostel made by taking a large apartment, filling it with secondhand mismatched furniture, and adding smart locks to the doors. 2 bathrooms are shared among everybody, along with a small kitchen and living/dining room. It’s completely unstaffed, and there’s a sign stating that if you want food, you can go to the pizza place downstairs. With that in mind, it’s mostly fine. The bed gets the job done. The cramped small room has only a TV and a small end table. The AC is cranked up high, and the extra blankets are all very stained and have holes. This was not properly listed and when I saw the owner there I mentioned that there was no mention of shared bathrooms. She got very defensive. Not a pleasant interaction. Not recommended unless it’s really cheap.
Stayed 2 nights in Sep 2025