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Dorothy's

3.0 star property

Photo gallery for Dorothy's

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

Reviews

8.4 out of 10
Very good

Popular amenities

  • Breakfast included
  • Pet-friendly
  • Kitchen
  • Laundry
  • Air conditioning
  • Free WiFi

Explore the area

View map
3445 N Halsted St, Chicago, IL, 60657
  • Place, Wrigley Field
    ‪8 min walk‬
  • Place, Vic Theatre
    ‪9 min walk‬
  • Place, Lincoln Park Zoo
    ‪4 min drive‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪22 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
  • Sleeps 2
  • 1 Double Bed

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

  • 5 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

  • 4 sq m
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

Free WiFi, bed sheets

City Single Room

  • 5 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

8.0 out of 10
Very good
(1 review)
  • 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 Twin 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 Twin Sofa Bed

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About the area

Chicago

With a stay at Dorothy's in Chicago (Lakeview), you'll be within a 5-minute drive of Wrigley Field and Lake Michigan. .This bed & breakfast is 3.6 mi (5.7 km) from Michigan Avenue and 4.5 mi (7.2 km) from 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 - 9 min walk - 0.8 km
  • Lincoln Park Zoo - 4 min drive - 3.2 km
  • Michigan Avenue - 7 min drive - 6.0 km

Getting around

  • Chicago Ravenswood 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
  • ‪Progress Bar Chicago - ‬2 min walk
  • ‪Replay Lakeview - ‬1 min walk
  • ‪Las Mañanitas - ‬2 min walk

About this property

Dorothy's

Bed & breakfast with free breakfast, 9-minute walk to Wrigley Field
Dorothy's offers 7 air-conditioned accommodations with shared/communal kitchens and hair dryers. Guests can make use of the in-room full-sized refrigerators/freezers and microwaves.

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

Make yourself at home in one of the 7 air-conditioned rooms featuring microwaves. Prepare your meals in the shared/communal kitchen. Complimentary wireless internet access is available to keep you connected. Bathrooms have showers and hair dryers.
Make use of convenient amenities, which include complimentary wireless internet access and a communal living room.
A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Featured amenities include luggage storage, laundry facilities, and microwave in a common area.
A complimentary continental breakfast is served each morning between 6:00 AM and 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 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 of 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 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
Cribs (infant beds) are not available

Payment types

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)
  • Housekeeping 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 elevators

Property is also known as

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

Dorothy's Reviews

Reviews

8.4

Very good

Rating 10 - Excellent. 49 out of 90 reviews
Rating 8 - Good. 22 out of 90 reviews
Rating 6 - Okay. 8 out of 90 reviews
Rating 4 - Poor. 6 out of 90 reviews
Rating 2 - Terrible. 5 out of 90 reviews

9.0/10

Cleanliness

7.8/10

Staff & service

8.6/10

Amenities

8.4/10

Property conditions & facilities

8.6/10

Eco-friendliness

Reviews

4/10 Poor

Stan

Travelled with family
Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service, room comfort

One star overall.

Place extremely difficult to locate. Took 15 minutes to locate upon arrival. No signs or labels anywhere. Bed small. Room small. Not enough for 2 adult males. Noise from people partying went on thru 5am.! Bar below room. Check in process rediculous. No live person at any time at all. No contact info beyond electronic. Checkout same. We already were gone by 2 hours when they requested checkout timeframe. Were texted to leave bedroom door open too late to do so. Neighborhood seems to be predominatly gay. We are NOT. Should be mentioned in advertising somewhere. Was unclear whether we were welcome to use common area or not. Place was clean. Showers/bathrooms nice
In town for Cubs game.
Stayed 1 night in Aug 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

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

6/10 Okay

Christopher

Travelled with family
Disliked: Staff & service, amenities, property conditions & facilities
Staff was nearly nonexistent. Arrived 20 minutes early. Texted owner and was told check in was 4:00, even though no one was there. Was told I could check in any time after 4:00, but wasn’t given access until 4:05. Room we stayed on was the 3rd floor. Room was very warm and could have used a ceiling fan. Breakfast was minimal and would have been a good chance to interact with the owner. Felt like owners wanted nothing to do with us.
Stayed 2 nights in Jul 2025

2/10 Terrible

Kenneth

No place to park
Stayed 1 night in Jul 2025

8/10 Good

Susan, South Bend

Travelled with group
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

Jeremy

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

10/10 Excellent

Steve, Hopkins

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

8/10 Good

TAMI, IOWA CITY

Travelled with family
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

10/10 Excellent

Geoffrey

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

Hit the lottery!

I had my scheduled accommodation bail on me last minute- it was a real bummer because it had parking and was close to Wrigley (my destination). Luckily, I found Dorothy's Place open and I reserved it. I found parking right around the corner, and it was really easy to get in and out and around the town. It is located in Boystown, which was a fun and safe vibe. I never felt endangered and the room was AWESOME. I had the suite with the bathroom- it was spacious, clean, and comfortable. It was like a 10 minute walk to Wrigley and all of the surrounding areas (I caught 3 games in my two nights!). I really felt like I had hit the lottery, not only because of the last-minute availability but because of the quality and the value. I would stay here in a flash if I were lucky enough to get back to the city!
Stayed 2 nights in Jul 2025

10/10 Excellent

Verified traveller

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

❤️❤️❤️

My bestie and I had a wonderful stay when we came for the Stray Kids concert! Cute room, free breakfast in the building next door, and room service from Big Gay Sal's Pizza downstairs! So good and so fun! Would love to come back!
Stayed 1 night in Jun 2025

8/10 Good

Jenny

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

10/10 Excellent

Lynn, Zionsville

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Near wrigley field
Stayed 1 night in Jun 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

Tanner

Stayed 1 night in Jun 2025

8/10 Good

Theodore

Travelled with partner
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

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