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Dorothy's

3.0 star property

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

8.4 out of 10
Very good

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Laundry
  • Kitchen

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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 refrigerator/freezer
Separate bedroom
Hair dryer
Microwave
Local meal delivery service
Shared/communal kitchen
  • 54 sq ft
  • 1 bedroom
  • 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 refrigerator/freezer
Separate bedroom
Hair dryer
Microwave
Local meal delivery service
Shared/communal kitchen
  • 50 sq ft
  • 1 bedroom
  • 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 refrigerator/freezer
Separate bedroom
Hair dryer
Microwave
Local meal delivery service
Shared/communal kitchen
  • 1 bedroom
  • 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 refrigerator/freezer
Separate bedroom
Hair dryer
Microwave
Local meal delivery service
Shared/communal kitchen
  • 50 sq ft
  • 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)

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Private bathroom
Hair dryer
Microwave
Local meal delivery service
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Apartment

Free WiFi, bed sheets

Basic Apartment

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
4 bedrooms
Hair dryer
2 bathrooms
Detached private bathroom
Microwave
  • 1197 sq ft
  • 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 refrigerator/freezer
5 bedrooms
Detached private bathroom
Hair dryer
Microwave
Local meal delivery service
  • 5 bedrooms
  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

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  • Free WiFi
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7.0 out of 10, Good, 973 reviews
$137 nightly
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About the neighborhood

Located in Lakeview, a neighborhood in Chicago, Dorothy's is in the entertainment district and near a metro station. Chicago Theatre and Art Institute of Chicago are cultural highlights, and travelers looking to shop may want to visit Michigan Avenue and Navy Pier. Looking to enjoy an event or a game? See what's going on at Wrigley Field or United Center. Visit our Chicago travel guide
View more B&B in Chicago
Map
3445 N Halsted St, Chicago, IL, 60657

What's nearby

  • Lincoln Park showing a city and a lake or waterhole
    Lincoln Park
    8 min walk - 0.5 miles
  • Wrigley Field showing a city and landscape views
    Wrigley Field
    8 min walk - 0.5 miles
  • Vic Theatre
    9 min walk - 0.5 miles
  • Anshe Emet Synagogue
    9 min walk - 0.5 miles
  • Theater Wit
    16 min walk - 0.9 miles

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

Bed & breakfast near Wrigley Field
Dorothy's provides amenities like free continental breakfast and laundry facilities. Guests can connect to free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • Luggage storage, local meal delivery service, and a TV in the lobby
  • Smoke-free premises
Room features
All guestrooms at Dorothy's boast comforts such as air conditioning, as well as amenities like free WiFi.
Extra amenities include:
  • Showers, hair dryers, and soap
  • Communal kitchens, full-sized refrigerators/freezers, and microwaves

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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 transportation

  • Free offsite parking within 0.2 miles
  • 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 elevator

More

  • Communal living room
  • Smoking not allowed

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
Information provided by the property may be translated using automated translation tools

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

Property 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
Safety features at this property include a fire extinguisher

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

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 Mar 6, 2026, prices found for a 1-night stay for 2 adults at Dorothy's on Mar 10, 2026 start from $111, 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?

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?

Check-out 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 15-minute walk of Wrigley Field and Lake Michigan. Lincoln Park and Vic Theatre are also within 15 minutes. Addison Station (Red Line) is 7 minutes by foot and Belmont Station (Red Line) is 11 minutes.

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Reviews

Dorothy's Reviews

8.4

Very Good

8.8

Cleanliness

8.6

Amenities

8.0

Staff & service

8.6

Property conditions & facilities
Rating 10 - Excellent. 60 out of 108 reviews
Rating 8 - Good. 27 out of 108 reviews
Rating 6 - Okay. 8 out of 108 reviews
Rating 4 - Poor. 7 out of 108 reviews
Rating 2 - Terrible. 6 out of 108 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

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

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

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

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

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

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

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

Anthony

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

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

10/10 Excellent

Verified traveler

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

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

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

Verified traveler

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

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

10/10 Excellent

Rodrigo

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quaint, convenient, and extremely friendly. Recommending it to all my friends traveling to Chicago.
Stayed 2 nights 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

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

8/10 Good

shiju

Liked: Amenities
No staff to assist. Room is clean and well. Parking is confusing. Breakfast is fine.
Stayed 2 nights in Dec 2024

6/10 Okay

Zachary

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

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

10/10 Excellent

Kenneth

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

Mike

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good area, easy transportation
Stayed 3 nights in Dec 2024