Skip to main content

Dorothy's

3.0 star property
Bed & breakfast with free breakfast, 9-minute walk to Wrigley Field

Choose dates to view prices

A short walk from Wrigley Field, Dorothy's provides free continental breakfast, laundry facilities and more. Stay connected with free in-room WiFi.
VIP Access

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$110
includes taxes & fees
2 Dec - 3 Dec

Get more when you're a member

  • Save 15% or more on select VIP Access properties when you reach Silver tier or above
  • Experience top-rated quality and exceptional service
  • Get an in-stay perk at select properties, plus free room upgrades, early check-in, and late check-out when available

Room options

Available filters for rooms
Showing 7 of 7 rooms

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
2 bathrooms
Hairdryer
Microwave
Freezer
Local meal delivery service
  • 5 sq m
  • Sleeps 2
  • 1 Double Bed

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
2 bathrooms
Hairdryer
Microwave
Freezer
Local meal delivery service
  • 5 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
2 bathrooms
Hairdryer
Microwave
Freezer
Local meal delivery service
  • 4 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
2 bathrooms
Hairdryer
Microwave
Freezer
Local meal delivery service
  • 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)

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
Private bathroom
Hairdryer
Microwave
Freezer
Local meal delivery service
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Apartment

Free WiFi, bed sheets

Basic Apartment

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
4 bedrooms
Hairdryer
Detached private bathroom
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
Hairdryer
Detached private bathroom
3 bathrooms
Microwave
  • 5 bedrooms
  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

You may also like

Ad
Outdoor spa tub

Homewood Suites by Hilton Aurora Naperville

Aurora
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
8.6 out of 10, Excellent, 706 reviews
The price is AU$227
includes taxes & fees
15 Dec - 16 Dec
Homewood Suites by Hilton Aurora Naperville
Mod logo
Sign in to view eligible discounts and perks. More rewards for more adventures!
Sign inSign up, it's free

About the area

Map
3445 N Halsted St, Chicago, IL, 60657

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
  • Briar Street Theatre - 9 min walk - 0.8 km
  • Advocate Illinois Masonic Medical Center - 14 min walk - 1.2 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 near Wrigley Field
Dorothy's provides amenities, such as free continental breakfast and laundry facilities. Guests can connect to free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • Smoke-free property, luggage storage and local meal delivery service
  • A TV in reception
Room features
All guest rooms at Dorothy's have comforts, such as air conditioning, as well as
Extra amenities include:
  • Showers, hairdryers and soap
  • Communal kitchens, full-sized fridge/freezers and microwaves

Similar properties

Exterior
The Villa Toscana
  • Pet-friendly
  • Parking included
  • Free WiFi
7.8 out of 10, Good, 619 reviews
The price is AU$123
includes taxes & fees
20 Nov - 21 Nov
The Villa Toscana

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 are 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.
Cots (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)
  • Cleaning/housekeeping/linen 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 any lifts

Property is also known as

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

Frequently asked questions

Is Dorothy's pet-friendly?

Yes, pets are allowed at this property. There's a fee of USD 25 per pet, per stay. Service animals are exempt from fees.

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

As of 19 Nov 2025, prices found for a 1-night stay for 2 adults at Dorothy's on 2 Dec 2025 start from AU$109.61, 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.

How much is parking at Dorothy's?

There is free parking nearby.

What time is check-in at Dorothy's?

Check-in start time: 4:00 PM; check-in end time: 10:00 PM. A fee applies for early check-in (subject to availability).

What time is check-out at Dorothy's?

Checkout is at noon. Late check-out is available for a fee (subject to availability).

Where is Dorothy's located?

Located in Lakeview, this bed & breakfast is within a 10-minute walk of Briar Street Theatre and Wrigley Field. Lake Michigan is 0.8 mi (1.3 km) away. Addison Station (Red Line) is 7 minutes by foot and Belmont Station (Red Line) is 11 minutes.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Dorothy's Reviews

8.4

Very good

8.8

Cleanliness

8.6

Amenities

7.8

Staff & service

8.6

Eco-friendliness

8.4

Property conditions & facilities
Rating 10 - Excellent. 50 out of 93 reviews
Rating 8 - Good. 23 out of 93 reviews
Rating 6 - Okay. 8 out of 93 reviews
Rating 4 - Poor. 7 out of 93 reviews
Rating 2 - Terrible. 5 out of 93 reviews

Reviews

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

Lisa

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

10/10 Excellent

Daniel

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

Philip

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

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

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

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

Vincient

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

Thomas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location to the Wrigley Field. That’s truly what we’re looking for. I did not realize that it was a communal bathroom, but I probably would’ve read what I was booking then I would’ve been aware of when I showed up.
Stayed 1 night in Jul 2025

8/10 Good

Joshua

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

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

10/10 Excellent

Gina

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

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

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

Steve

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

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

8/10 Good

TAMI

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

Verified traveller

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

10/10 Excellent

Lynn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Near wrigley field
Stayed 1 night in Jun 2025

10/10 Excellent

Anthony

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

8/10 Good

Susan

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

8/10 Good

Missy

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

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