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Dorothy's

2.0 star property

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Photo gallery for Dorothy's

Living area - Dorothy's (Chicago)
Shower, hair dryer, towels, soap - Dorothy's (Chicago)
Free daily continental breakfast - Dorothy's (Chicago)
Living area - Dorothy's (Chicago)
Free WiFi, bed sheets - Dorothy's (Chicago)
A short walk from Wrigley Field, Dorothy's provides amenities like free continental breakfast. Stay connected with free in-room WiFi.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Kitchen

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)
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

10.0 out of 10
Exceptional
(1 review)
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

7.0 out of 10
Good
(4 reviews)
  • 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

9.8 out of 10
Exceptional
(6 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 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

About the neighborhood

Located in Lakeview, a neighborhood in Chicago, Dorothy's is in the entertainment district and near a metro station. Chicago History Museum and Chicago Theatre 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
    Lincoln Park
    8 min walk - 0.5 miles
  • Wrigley Field
    Wrigley Field
    8 min walk - 0.5 miles
  • Vic Theatre
    11 min walk - 0.6 miles
  • Wrigley View Rooftop
    13 min walk - 0.7 miles
  • Theater Wit
    17 min walk - 1.0 mile

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
  • The Chicago Diner
    1 min walk
  • Replay Lakeview
    1 min walk

About this property

Dorothy's

Bed & breakfast near Wrigley Field
Dorothy's provides free continental breakfast and more. Guests can connect to free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • Luggage storage, a TV in the lobby, and local meal delivery service
  • 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, mini fridges, 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 microwave
  • Mini-fridge

Conveniences

  • 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

  • Freezer
  • Meal delivery service
  • Microwave
  • Mini-fridge
  • Paper towels
  • Restaurant dining guides
  • Shared kitchen access

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 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

8.6

Excellent

9.0

Cleanliness

8.6

Amenities

8.2

Staff & service

8.6

Property conditions & facilities
Rating 10 - Excellent. 66 out of 116 reviews
Rating 8 - Good. 29 out of 116 reviews
Rating 6 - Okay. 8 out of 116 reviews
Rating 4 - Poor. 7 out of 116 reviews
Rating 2 - Terrible. 6 out of 116 reviews

Reviews

Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
First time at Dorothy's but I've stayed at her sister location so I know the owner/management and what to expect. Great location and the building is kept up very well. My only non happy comment was no dresser in this room. Its ok since this visit was just me. Being able to use a full kitchen and store food in the refrigerator is a major plus
Stayed 4 nights in Apr 2026
Verified

8/10 Good

Erica

Liked: Cleanliness, property conditions & facilities
Automated check-in worked well, waffles were great
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I stayed here during a week of business etc and found the accommodations excellent for a long-ish stay. My room was the Purple Room - private bath, dining area, living room and separate bedroom. Clean, quiet, comfortable and appointed with everything one would need: Coffee maker, small fridge, microwave, dishes. Plenty of towels and storage in the bathroom. Big comfortable sectional sofa to lounge/work on. The staff is off site and responded quickly to text messages. The lock code provided easy and safe access to the room. VERY fun neighborhood - walking distance to everything, including Chicago's beautiful lakefront.
Stayed 6 nights in Mar 2026
Verified

10/10 Excellent

James

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
What an absolutely amazing room, made me feel like home. Wonderful apartment in the middle of everything.
Stayed 1 night in Dec 2025
Verified

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
Verified

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
Verified

8/10 Good

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This time, I stayed in the Blue Room, which shares two bathrooms, a well-stocked kitchen, and living space with 2 other bedrooms. I wasn't sure what to expect, but it turned out to be fine. I only encountered one other guest during my overnight stay and it was very quiet (with the exception of typical urban noise outside, which doesn't bother me at all). My only complaint was the bedroom door - there's a deadbolt AND a chain lock, but there's a small gap between the door and the side jamb that felt a little weird to me. I got over it, though :) Also, be forewarned that this is on the third floor of the home and the stairs might be too steep for some. If you don't take advantage of the free breakfast next door, do yourself a favor and walk across Cornelia to the Roggenart bakery. Absolutely divine!
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Daniel

Liked: Cleanliness, amenities
Clean room beautiful.yards convenient
Stayed 2 nights in Aug 2025
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Anthony

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

10/10 Excellent

Mark

Liked: Cleanliness, amenities, property conditions & facilities
The room was small, but very comfortable. Initially, I was a bit leery of the "no reception; we'll send you a code" check-in, but it went very smoothly. The code worked on all the doors it was supposed to work on, and I appreciated the triple-layer of code security - outside door, door to the floor, door to the room. Dorothy's is ideally situated, and easy walking distance to attractions in the area, in addition to the Red line train and numerous bus lines. If I had to ding Dorothy's on anything, it's this: Coffeemate isn't cream and doesn't do the same in your coffee in the morning as does half-and-half.
Stayed 3 nights in Dec 2025
Verified

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
Verified

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
Verified

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
Verified

8/10 Good

Mike

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

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
Verified

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
Verified

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
Verified

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
Verified

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