Dorothy's

B&B convenient to Wrigley Field

Choose dates to view prices

Thu, Feb 19
Fri, Feb 20
February 2026
18
March 2026
Dorothy's offers a great location, putting you within a 15-minute walk of Wrigley Field and Lake Michigan. Free perks include WiFi and continental breakfast daily between 6:00 AM and 10:00 AM. Also, Michigan Avenue and Chicago Riverwalk are within a short drive. Public transportation is just a short walk: Addison Station (Red Line) is 7 minutes and Belmont Station (Red Line) is 11 minutes.
VIP Access
Very good

Popular amenities

  • Pet friendly
  • Parking available
  • Free WiFi
  • Air conditioning
  • Laundry facilities

Main amenities (8)

  • Housekeeping (on request)
  • Air conditioning
  • Communal living room
  • Microwave in a common area
  • Refrigerator in a common area
  • Self-serve laundry
  • Luggage storage
  • TV in a common area

Feel at home (4)

  • Cookware, dishware, and utensils
  • Laundry facilities
  • Free parking nearby
  • Hair dryer
CA $43
CA $98 total
includes taxes & fees
Feb 25 - Feb 26

Room options

Showing 7 of 7 rooms
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Free WiFi, bed sheets
Free WiFi, bed sheets

Basic Single Room

Wonderful

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Hair dryer
Microwave
Local meal delivery service
Shared/communal kitchen
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Free WiFi, bed sheets
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
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Free WiFi, bed sheets
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
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Free WiFi, bed sheets
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
  • 5 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Free WiFi, bed sheets
Free WiFi, bed sheets

Standard Studio

Exceptional

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Separate bedroom
Hair dryer
Private bathroom
Microwave
Local meal delivery service
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Free WiFi, bed sheets
Free WiFi, bed sheets

Basic Apartment

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
4 bedrooms
2 bathrooms
Hair dryer
Detached private bathroom
Microwave
  • 111 sq m
  • 4 bedrooms
  • Sleeps 9
  • 2 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed
Shower, hair dryer, towels, soap
Free WiFi, bed sheets
Free WiFi, bed sheets
Free WiFi, bed sheets

City Apartment

Highlights

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

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About the area

Map
3445 N Halsted St, Chicago, IL, 60657

What's nearby

  • Wrigley Field - 6 min walk - 0.6 km
  • Vic Theatre - 9 min walk - 0.8 km
  • Lincoln Park - 9 min walk - 0.8 km
  • Wrigley View Rooftop - 11 min walk - 1.0 km
  • Theater Wit - 14 min walk - 1.2 km

Getting around

  • Chicago O'Hare Intl. Airport (ORD) - 45 min drive
  • Chicago Midway Airport (MDW) - 48 min drive
  • Chicago, IL (PWK-Chicago Executive) - 53 min drive
  • Chicago, IL (DPA-Dupage) - 86 min drive
  • Rockford, IL (RFD-Greater Rockford) - 106 min drive
  • Chicago Ravenswood Station - 5 min drive
  • Chicago Clybourn Station - 5 min drive
  • Chicago Irving Park Station - 8 min drive
  • Addison Station (Red Line) - 7 min walk
  • Belmont Station (Red Line) - 11 min walk
  • Wellington Station - 16 min walk

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

Dorothy's offers a great location, putting you within a 15-minute walk of Wrigley Field and Lake Michigan. Free perks include WiFi and continental breakfast daily between 6:00 AM and 10:00 AM. Also, Michigan Avenue and Chicago Riverwalk are within a short drive. Public transportation is just a short walk: Addison Station (Red Line) is 7 minutes and Belmont Station (Red Line) is 11 minutes.

At a glance

Hotel size

    • 7 rooms

Arriving/Leaving

    • Check-in start time: 4:00 PM; Check-in end time: 10:00 PM
    • Early check-in subject to availability
    • Minimum check-in age: 18
    • Check-out time is noon
    • Late check-out subject to availability

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

Required at check-in

    • Credit card, debit card, or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 18

Children

    • No cribs (infant beds)

Pets

    • Pets allowed*
    • Service animals welcome

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms (speed: 25+ Mbps)

Parking

    • Free offsite parking within 0.2 mi
    • Street parking available

Other information

    • Smoke-free property

Property amenities

Food and drink

  • Free continental breakfast each morning 6:00 AM–10:00 AM
  • Shared microwave
  • Shared refrigerator

Services

  • Laundry facilities
  • Luggage storage
  • Virtual front desk

Facilities

  • Television in common areas
  • Communal living room

Accessibility

  • 30 stairs to reach property

Room amenities

Home comfort

  • Air conditioning and heating

Sleep well

  • Bed sheets provided

Freshen up

  • Shower only
  • Soap
  • Hair dryer
  • Towels
  • Toilet paper

Stay connected

  • Free WiFi (speed of 25+ Mbps)

Food and drink

  • Meal delivery service
  • Full-sized refrigerator/freezer
  • Freezer
  • Microwave
  • Shared kitchen access
  • Toaster oven
  • Cookware, dishes, and utensils
  • Paper towels

More

  • Housekeeping on request (surcharge)
  • Restaurant dining guide

Fees & policies

Optional extras

  • Early check-in can be arranged for an extra charge (subject to availability)
  • Late check-out can be arranged for an extra charge (subject to availability)
  • Housekeeping is offered for an extra charge of USD 5 per day

Pets

  • Service animals exempt from fees
  • Pets are allowed for an extra charge of USD 25 per pet, per stay

Policies

This property does not have elevators.
This property accepts credit cards and debit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover

Also known as

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

Frequently asked questions

Are pets allowed at Dorothy's?

Yes, pets are welcome. There's a charge of USD 25 per pet, per stay. Service animals are exempt from fees.

Is parking offered on site at Dorothy's?

No, unfortunately, but there's free parking nearby.

What are the check-in and check-out times at Dorothy's?

Check-in start time: 4:00 PM; Check-in end time: 10:00 PM. There's a charge for early check-in (subject to availability). Check-out time is noon. Late check-out is available for a charge (subject to availability).

Is there an onsite casino at Dorothy's?

No, this bed & breakfast doesn't have a casino, but Bally's Casino Chicago (7-min drive) and Rivers Casino (18-min drive) are both nearby.

What's the area around Dorothy's like?

Dorothy's is a short 7-minute walk from Addison Station (Red Line) and 9 minutes' walk from Wrigley Field.

Have a question?

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

Dorothy's Reviews

8.4

Very good

8.8

Cleanliness

8.6

Amenities

8.0

Staff & service

8.6

Property conditions & facilities

What guests liked

  • Breakfast options were available next door with a variety of choices to serve yourself. (3 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

8/10 Very good

Automated check-in worked well, waffles were great
Erica, 2-night trip

10/10 Exceptional

What an absolutely amazing room, made me feel like home. Wonderful apartment in the middle of everything.
James, 1-night trip

10/10 Exceptional

Can’t beat the price or location. Everything seemed clean and I loved the waffles.
Ashley, 1-night trip

8/10 Very good

Halsted is a nice neibourhood. We liked the secondhand shops.
Lisa, 3-night trip

10/10 Exceptional

Clean room beautiful.yards convenient
Daniel, 2-night trip

8/10 Very good

I enjoyed my stay.
Philip, 3-night trip

10/10 Exceptional

Quick overnight visit and 5th stay at this property. Everything on point as usual!
1-night trip

10/10 Exceptional

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.
Helen, 5-night trip

10/10 Exceptional

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.
Rae, 1-night trip

10/10 Exceptional

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.
Lisa, 9-night trip

10/10 Exceptional

Great little spot with all you need. Clean, cozy and a great breakfast!
Joshua, 1-night trip

10/10 Exceptional

Great location. Super clean and close to transit for easy access to anywhere you need to go.
Jose, 3-night trip

10/10 Exceptional

Just breakfast no good… noise but I was advised, everything else is perfect!
Fernando Emmanuel, 4-night trip

8/10 Very good

Incredibly pleased with rooms/suite. Disappointed in having a cold shower and my husband skipped his. I have been informed that the water issue had been resolved this morning.
Steve, 1-night trip

10/10 Exceptional

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.
Thomas, 1-night trip

4/10 Fair

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.
John, 1-night trip

10/10 Exceptional

Love the coziness of the location and th area is nice and safe
Anthony, 2-night trip

10/10 Exceptional

Above a pizza place with great specials offered and the decor was a mix of what looked like a different decor for each room
Steve, 1-night trip

10/10 Exceptional

Perfect for a night. Nice shared living space and 2 bathrooms. Didn’t have any issues or even see anyone else there
Colin, 1-night trip

10/10 Exceptional

Very Comfy

Super clean, quiet, comfortable place to stay. Will definitely be returning
2-night trip

4/10 Fair

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.
Troy, 1-night trip

8/10 Very good

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.
Joshua, 4-night trip

10/10 Exceptional

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!
Gina, 1-night trip

10/10 Exceptional

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.
Vincient, 2-night trip

10/10 Exceptional

We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!
Keely, 1-night trip