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Dorothy's

Property class: 2

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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

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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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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

9.8 out of 10
Exceptional
(7 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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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 modern skyscrapers and a park with autumn trees and a lake.
    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
  • 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
    3 min walk
  • Roscoe's
    2 min walk
  • The Sports Corner Bar & Grill
    8 min walk
  • Happy Camper
  • Cell Block
    6 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 a TV in the lobby
    • Local meal delivery service
  • 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

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 Aug 20, 2026, prices found for a 1-night stay for 2 adults at Dorothy's on Aug 24, 2026 start from $120, 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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