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Dorothy's

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

Photo gallery for Dorothy's

Free WiFi, bed sheets
Free WiFi, bed sheets
Shower, hair dryer, towels, soap
Full-sized fridge, microwave, toaster oven, cookware/dishes/utensils
Living area

Reviews

8.4 out of 10
Very good

Popular amenities

  • Breakfast included
  • Pet-friendly
  • Kitchen
  • Laundry
  • Air conditioning
  • Free WiFi
The current price is AU$197
includes taxes & fees
29 Sept - 30 Sept

Explore the area

View map
3445 N Halsted St, Chicago, IL, 60657
  • Wrigley Field
    ‪8 min walk‬
  • Lincoln Park Zoo
    ‪3 min drive‬
  • Michigan Avenue
    ‪6 min drive‬
  • Chicago, IL (ORD-O'Hare Intl.)
    ‪22 min drive‬

Room options

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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Omni Chicago Hotel

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  • Pet-friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.6 out of 5, Wonderful, 1,567 reviews
The price is AU$423
includes taxes & fees
24 Sept - 25 Sept
Omni Chicago Hotel

About the area

Chicago

At Dorothy's you'll be within a 20-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.
View more B&B in ChicagoOpens in a new window

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
  • ‪The Chicago Diner - ‬2 min walk
  • ‪Elixir Lounge - ‬1 min walk

About this property

Dorothy's

Bed & breakfast with free breakfast, a short walk to Wrigley Field
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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The Villa Toscana

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The price is AU$226
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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)

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: 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
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. 

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 10 Sept 2025, prices found for a 1-night stay for 2 adults at Dorothy's on 29 Sept 2025 start from AU$196.91, 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. 40 out of 72 reviews
Rating 8 - Good. 15 out of 72 reviews
Rating 6 - Okay. 8 out of 72 reviews
Rating 4 - Poor. 4 out of 72 reviews
Rating 2 - Terrible. 5 out of 72 reviews

9.0/10

Cleanliness

7.8/10

Staff & service

8.6/10

Amenities

8.4/10

Property conditions & facilities

8.4/10

Eco-friendliness

Reviews

10/10 Excellent

Alexis

Stayed 1 night in Jun 2025

10/10 Excellent

Joshua

Travelled with partner
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

Jose

Travelled with partner
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

8/10 Good

Karen

Stayed 1 night in May 2025

10/10 Excellent

Vito

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in May 2025

10/10 Excellent

Frederic

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in May 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

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

10/10 Excellent

Nate

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

8/10 Good

Douglas

Business traveller
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I was charged twice for one hotel night
Stayed 1 night in May 2025

10/10 Excellent

JOSE HUMBERTO CORRALES

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

6/10 Okay

Wendy

Travelled with family, Business traveller
Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
Parking is difficult. Closest designated spot was 2 blocks away. Booking was easy enough but communication between site and accommodation was inefficient. Email was not passed on for final access instructions to unmanned accommodation site. The finalisation process did not allow for visitors with International phone numbers to be contacted directly either. Login does not accept driver's licence picture.
Stayed 1 night in Apr 2025

6/10 Okay

Frank

Disliked: Staff & service, property conditions & facilities

Dissatisfied with our stay

Dissatisfied with our stay!! Our experience was less desirable than expected. Normal and customary check in time is 3pm, we couldn’t check in until 4 without added cost. This is in a predominantly LGBT neighborhood, not mentioned. The “quirky” old building was just not maintained well, so in disrepair rather than quirky. Mold around the shower floor. Tiny room with shared bathroom, not mentioned in description. The distance to Wrigley Field was only about a ten minute walk, which was great!
Stayed 2 nights in Apr 2025

6/10 Okay

Zachary

Travelled with partner
Disliked: Staff & service
The property itself is in a great location and offers good value for the price. However, the experience was unfortunately overshadowed by poor customer service. Upon booking, we received multiple links with different sets of information—one with property details, another with check-in instructions, and other links as well. Assuming there was a master link as the webpage seemed to suggest, we missed the one specifically for check-in. When we arrived just after 4pm on 04/17, we used the keypad to contact the property for assistance. The woman who answered the call was unnecessarily rude and dismissive—something that could have been avoided with a simple, helpful response. A little courtesy goes a long way, especially in hospitality. The stay itself was fine, but the unprofessional attitude of certain staff members left a lasting negative impression. With better communication and a more respectful approach to guests, this property could truly stand out.
Stayed 1 night in Apr 2025

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

6/10 Okay

Arkadiusz

Liked: Cleanliness, property conditions & facilities, room comfort
Disliked: Staff & service
Stayed 1 night in Mar 2025

2/10 Terrible

Lakshmikant

Business traveller
Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
The street was always very noisy
Stayed 4 nights in Mar 2025

10/10 Excellent

Katherine

Stayed 1 night in Mar 2025

10/10 Excellent

Keely

Travelled 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 traveller
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