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Dorothy's

3.0 star property
B&B convenient to Wrigley Field

Choose dates to view prices

At Dorothy's, you'll be just a 5-minute drive from 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

Reviews

8.4 out of 10
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
$67 nightly
The total price is $72
Dec 22 - Dec 23
Total with taxes and fees

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
Hair dryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 54 sq ft
  • 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
Hair dryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 50 sq ft
  • 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
Hair dryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 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
Hair dryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 50 sq ft
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

9.0 out of 10
Wonderful
(2 reviews)

Highlights

Air conditioning
Heating
Full-sized refrigerator/freezer
Hair dryer
Private bathroom
Microwave
Local meal delivery service
Freezer
  • 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
2 bathrooms
Hair dryer
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
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 neighborhood

Map
3445 N Halsted St, Chicago, IL, 60657

What's nearby

  • Lincoln Park - 8 min walk - 0.7 km
  • Wrigley Field - 8 min walk - 0.7 km
  • Vic Theatre - 9 min walk - 0.8 km
  • Briar Street Theatre - 9 min walk - 0.8 km
  • Advocate Illinois Masonic Medical Center - 14 min walk - 1.2 km

Getting around

  • Chicago Midway Airport (MDW) - 45 min drive
  • Chicago O'Hare Intl. Airport (ORD) - 48 min drive
  • Chicago, IL (PWK-Chicago Executive) - 54 min drive
  • Chicago, IL (DPA-Dupage) - 88 min drive
  • Rockford, IL (RFD-Greater Rockford) - 107 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

  • ‪Roscoe's - ‬2 min walk
  • ‪Progress Bar Chicago - ‬2 min walk
  • ‪Hydrate - ‬1 min walk
  • ‪Replay Lakeview - ‬1 min walk
  • ‪Las Mañanitas - ‬2 min walk

About this property

Dorothy's

At Dorothy's, you'll be just a 5-minute drive from 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

DONE

Hotel size

    • 7 rooms
DONE

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
DONE

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
DONE

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
DONE

Children

    • No cribs (infant beds)
DONE

Pets

    • Pets allowed*
    • Service animals welcome
WIFI

Internet

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

Parking

    • Free offsite parking within 0.2 mi
    • Street parking available
DONE

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.

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Reviews

Dorothy's Reviews

8.4

Very Good

8.8

Cleanliness

8.6

Amenities

8.0

Staff & service

8.6

Eco-friendliness

8.4

Property conditions & facilities

Guest review summary

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.

Reviews

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

Clean room beautiful.yards convenient
Daniel, 2-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

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

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 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

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

Very Comfy

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

❤️❤️❤️

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!
1-night trip

8/10 Very good

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.
Susan, 1-night trip

10/10 Exceptional

Quaint, convenient, and extremely friendly. Recommending it to all my friends traveling to Chicago.
Rodrigo, 2-night trip

8/10 Very good

The property was clean, easy check-in. My only complaint is that wifi wasn't working.
Timothy, 1-night trip

10/10 Exceptional

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!
Geoffrey, 2-night trip

8/10 Very good

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.♥️😊
antoinette lewis, 2-night trip

8/10 Very good

No staff to assist. Room is clean and well. Parking is confusing. Breakfast is fine.
shiju, 2-night trip

6/10 Good

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.
Zachary, 1-night trip

8/10 Very good

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.
Konrad, 3-night trip

8/10 Very good

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.
Sean, 1-night trip

10/10 Exceptional

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!
Kenneth, 3-night trip

8/10 Very good

Good area, easy transportation
Mike, 3-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

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