Dorothy's

Property class: 2

Choose dates to view prices

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

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

A bedroom with a bed, green and red pillows, a painting on the wall, and a window with curtains.

Basic Single Room

9.0 out of 10
Wonderful
(4 reviews)
  • 54 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for Economy Single Room

A bedroom with a wooden door, a bed with blue bedding, two framed artworks on the wall, and a small bedside table.

Economy Single Room

10.0 out of 10
Exceptional
(2 reviews)
  • 50 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

A bedroom with a bed, a ceiling fan, and three framed pictures on the wall.

Standard Single Room

7.8 out of 10
Good
(6 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

A bedroom with a bed, a window, a painting, and a nightstand.

City Single Room

  • 50 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Studio

A bedroom with a bed, a nightstand, a lamp, a wall-mounted picture, and a wall sconce.

Standard Studio

9.4 out of 10
Exceptional
(8 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Apartment

A bedroom with a wooden door, a bed with blue bedding, two framed artworks on the wall, and a small bedside table.

Basic Apartment

  • 1197 sq ft
  • 4 bedrooms
  • Sleeps 9
  • 2 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

View all photos for City Apartment

A bedroom with a wooden door, a bed with blue bedding, two framed artworks on the wall, and a small bedside table.

City Apartment

  • 5 bedrooms
  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

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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

  • A city skyline with a river, green spaces, and a baseball field.
    Lincoln Park
    8 min walk - 0.5 miles
  • An aerial view of a baseball stadium surrounded by urban buildings.
    Wrigley Field
    8 min walk - 0.5 miles
  • Center on Halsted
    6 min walk - 0.4 miles
  • Vic Theatre
    11 min walk - 0.6 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
    3 min walk
  • Roscoe's
    2 min walk
  • Replay Lakeview
    1 min walk
  • Progress Bar Chicago
    2 min walk
  • The Chicago Diner
    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:
    • Smoke-free premises, luggage storage, and local meal delivery service
    • A TV in the lobby
  • 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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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 Oct 23, 2026, prices found for a 1-night stay for 2 adults at Dorothy's on Nov 17, 2026 start from $154, 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

8.6

Excellent

9.0

Cleanliness

8.8

Amenities

8.2

Staff & service

8.6

Property conditions & facilities
Rating 10 - Excellent. 112 out of 193 reviews
Rating 8 - Good. 45 out of 193 reviews
Rating 6 - Okay. 15 out of 193 reviews
Rating 4 - Poor. 12 out of 193 reviews
Rating 2 - Terrible. 9 out of 193 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun unique apartment above a wonderful pizza place! Great location and the stay was just great!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Space was so clean and modern. Breakfast was good also. Very nice stay.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, just what we needed.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was a very peaceful and fabulous stay. The room was beautiful and comfortable, I had no issues with noise as I had seen in other reviews. The breakfast options were pretty generous and I felt very relaxed the whole time. Thank you for a lovely stay!
Stayed 5 nights in Jul 2026
Verified review

6/10 Okay

Liked: Cleanliness
Dorothy's is a nice place for people wanting easy access to a clean, SRO-style room in a good location with an invisible staff (online checkin). Specific complaints: my room lacked both trash can and bedside light. And the self-serve breakfast provided nice individual portions of yogurt and bags of nuts, but on neither morning was coffee available (happily there are places only blocks away to buy some). Plus, charging extra for checking in 1-3-hours earlier than the 4pm check-in seems a little tacky (I've been traveling for many decades and never confronted this add-on).
Stayed 2 nights in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I stayed 4 nights, we liked the cleanliness, the location, the value and having the option of breakfast. My only concern was the room being very small and we had to share the bathroom. But in general it was a quiet good location.
Stayed 4 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness
lots of clean rooms and clean bathrooms with products you can use. keep in mind however that not every room has its own private bathroom
Stayed 1 night in May 2026
Verified review

8/10 Good

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

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

8/10 Good

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

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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