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Dorothy's

3.0 star property
Bed & breakfast with free breakfast, 9-minute walk to Wrigley Field

Photo gallery for Dorothy's

Living area
Shower, hair dryer, towels, soap
Free daily continental breakfast
Living area
Free WiFi, bed sheets

Reviews

8.4 out of 10
Very good

Popular amenities

  • Breakfast included
  • Pet-friendly
  • Kitchen
  • Laundry
  • Air conditioning
  • Free WiFi
The current price is AU$119
includes taxes & fees
4 Jan - 5 Jan 2026

Explore the area

View map
3445 N Halsted St, Chicago, IL, 60657
  • Place, Lincoln Park
    ‪8 min walk‬
  • Place, Wrigley Field
    ‪8 min walk‬
  • Place, Vic Theatre
    ‪9 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪23 min drive‬

Room options

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 fridge/freezer
Hairdryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 5 sq m
  • 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 fridge/freezer
Hairdryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 5 sq m
  • 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 fridge/freezer
Hairdryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 4 sq m
  • 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 fridge/freezer
Hairdryer
2 bathrooms
Microwave
Local meal delivery service
Freezer
  • 5 sq m
  • 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 fridge/freezer
Hairdryer
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 fridge/freezer
4 bedrooms
2 bathrooms
Hairdryer
Detached private bathroom
Microwave
  • 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

Highlights

Air conditioning
Heating
Full-sized fridge/freezer
5 bedrooms
3 bathrooms
Hairdryer
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

Chicago

At Dorothy's you'll be within a 20-minute stroll of popular places like Wrigley Field and Lake Michigan. Highlights at this B&B include free continental breakfast. .This pet-friendly bed & breakfast offers free WiFi in public areas, luggage storage and a communal living room. Other amenities include laundry facilities, a microwave in a common area and a fridge in a common area. Each morning free breakfast is served. There's also the convenience of free parking nearby. .Attractions within a 10-minute drive of this 3-property class Lakeview B&B include Michigan Avenue and Chicago Riverwalk.
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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 Ravenswood Station - 5 min drive
  • Addison Station (Red Line) - 7 min walk
  • Chicago Midway Airport (MDW) - 45 min drive

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

Bed & breakfast with free breakfast, 9-minute walk to Wrigley Field
Free breakfast is available daily. Public spaces have free WiFi. Dorothy's also features laundry facilities, a communal living room, and a microwave in a common area.

This 3-star Chicago bed & breakfast is smoke free.

  • 7 guestrooms or units
  • Continental breakfast (free)
  • Self-service laundry
  • Storage area for luggage
  • Television in lobby
  • No smoking on site
  • Microwave in a common area
  • Fridge in a common area
Dorothy's offers 7 air-conditioned accommodations with shared/communal kitchens and a hairdryer. Guests can make use of the in-room full-sized fridge/freezers and microwaves.

Bathrooms include a shower. This Chicago bed & breakfast provides complimentary wireless Internet access, with a speed of 25+ Mbps. Housekeeping is provided on request.

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4 Jan - 5 Jan 2026
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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 transport

  • Free offsite parking within 322 metres
  • 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 full-sized refrigerator/freezer
  • In-room microwave
  • Laundry facilities

Conveniences

  • Laundry facilities
  • Luggage storage
  • Shared microwave
  • Shared refrigerator
  • Virtual front desk

Guest services

  • Housekeeping (on request)

Accessibility

  • 30 steps to reach entrance
  • No lift

More

  • Communal living room
  • Smoke-free property

Room amenities

Bedroom

  • Bedsheets provided

Bathroom

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

Food and drink

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

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 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: USD 25 per pet, per stay
    • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Cots (infant beds) are not available.

Payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • 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)
  • Cleaning/housekeeping/linen fee: USD 5 per day

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property accepts Visa, Mastercard, American Express, Discover and debit cards. Cash is not accepted. 

Property is also known as

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

Frequently asked questions

Are there any beaches close to Dorothy's?

The closest beach to Dorothy's is Montrose Beach (2.6 km).

How much does it cost to stay at Dorothy's?

As of 11 Dec 2025, prices found for a 1-night stay for 2 adults at Dorothy's on 4 Jan 2026 start from AU$118.59, 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.

Does Dorothy's serve breakfast?

You bet, free continental breakfast is served daily from 6:00 AM to 10:00 AM.

Is there a free airport shuttle available at Dorothy's?

No, Dorothy's does not offer an airport shuttle service.

What time are check-in & check-out at Dorothy's?

Check-in begins at 4:00 PM. Check-out time is noon.

Reviews

Dorothy's Reviews

8.4

Very good

8.8/10

Cleanliness

8.0/10

Staff & service

8.6/10

Amenities

8.4/10

Property conditions & facilities

8.6/10

Eco-friendliness
Rating 10 - Excellent. 52 out of 97 reviews
Rating 8 - Good. 24 out of 97 reviews
Rating 6 - Okay. 8 out of 97 reviews
Rating 4 - Poor. 7 out of 97 reviews
Rating 2 - Terrible. 6 out of 97 reviews

Reviews

10/10 Excellent

Rae

Travelled with family
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

6/10 Okay

Joanne

Disliked: Staff & service

Near Wrigley Field..but don't expect much else

Documents on how to enter the property were sent the day before we checked in..and that the access code would be available at 4pm. This was fine for the first step, but on the second, use of the access code was not listed so we couldn't get into the room. There was no one on site to help, everything was through WhatsApp. The room was small..the bed was flush against the window and i had to crawl over my husband if i wanted to get out. There were 2 shared bathrooms, not mentioned in the description. Nor was the two huge flight of stairs to get to the room. Breakfast is available, but we only tried once. After a waffle came out burnt (the iron looked like it needed a good clean) we went out to eat. It was close to Wrigley Field...one positive. All in all, really can't recommend staying here.
Stayed 4 nights in Sep 2025

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

10/10 Excellent

Daniel

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

10/10 Excellent

Lisa

Travelled with pets
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

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Quick overnight visit and 5th stay at this property. Everything on point as usual!
Stayed 1 night in Aug 2025

8/10 Good

Ann

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Wrigleyville gem

We wanted to stay in Wrigley Field near the CTA. Dorothy's was a perfect choice for that. We were there two nights and appreciated having the studio apartment. Not only did we have an ensuite bathroom but also a large sitting room that included a table/chairs, fridge coffee maker and microwave. Plenty of restaurants to chose from. The downside for me was the noise from the pizza parlor downstairs and across the street. If you are a light sleeper, earplugs are advised. The staircase is steep and narrow. ( just so you know) Being there was a trip down memory lane. A fun stay for certain! Breakfast is next door and plenty of choices to serve yourself.
Stayed 2 nights in Aug 2025

10/10 Excellent

Joshua

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in Aug 2025

10/10 Excellent

Connor

Stayed 3 nights in Jul 2025

4/10 Poor

John

Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

4/10 Poor

Gary

Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort

Not the Best

Said they had parking was street parking and the streets were packed. The feeling was breakfast like a B&B but cereal, waffle maker and some pastries and no coffee made, empty pot. Security is like a prison. lock boxes everywhere. 3rd floor, steps. More of a hostel than a hotel. They had a 4pm check in. We found a parking place 20 minutes before 4 and I asked for my code to get in and they refused. It came at 4. The place was old, the room tiny and it was not cheap. I would not go here again. No one there so you have to do things for yourself. You have to go online and fill out registration which includes picture of yourself and you drivers license because no one will be around. A hassle I have never experienced with a hotel. I had trouble getting to their websites cause their attached web address's were not links. I had to write them down and type them into my phone. Tried on my computer but you can't copy a picture into their site for the drivers license. You have to take a live picture and my computer didn't like that. Just aggravation that you don't need at the price of a decent hotel.
Stayed 1 night in Aug 2025

4/10 Poor

Gaston

Travelled with group
Liked: Cleanliness
Disliked: Staff & service, property conditions & facilities, room comfort
It’s very weird. I felt like I was breaking in a house
Stayed 1 night in Jul 2025

6/10 Okay

Travis

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
I hated that they're was absolutely know communication except through text. Have a question text. Need to ask something text. Building was nice but a little loud but not to bad. Just poor communication.
Stayed 1 night in Jul 2025

4/10 Poor

Stan

Travelled with family
Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service, room comfort

One star overall.

Place extremely difficult to locate. Took 15 minutes to locate upon arrival. No signs or labels anywhere. Bed small. Room small. Not enough for 2 adult males. Noise from people partying went on thru 5am.! Bar below room. Check in process rediculous. No live person at any time at all. No contact info beyond electronic. Checkout same. We already were gone by 2 hours when they requested checkout timeframe. Were texted to leave bedroom door open too late to do so. Neighborhood seems to be predominatly gay. We are NOT. Should be mentioned in advertising somewhere. Was unclear whether we were welcome to use common area or not. Place was clean. Showers/bathrooms nice
In town for Cubs game.
Stayed 1 night in Aug 2025

10/10 Excellent

Colin

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect for a night. Nice shared living space and 2 bathrooms. Didn’t have any issues or even see anyone else there
Stayed 1 night in Jul 2025

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

6/10 Okay

Christopher

Travelled with family
Disliked: Staff & service, amenities, property conditions & facilities
Staff was nearly nonexistent. Arrived 20 minutes early. Texted owner and was told check in was 4:00, even though no one was there. Was told I could check in any time after 4:00, but wasn’t given access until 4:05. Room we stayed on was the 3rd floor. Room was very warm and could have used a ceiling fan. Breakfast was minimal and would have been a good chance to interact with the owner. Felt like owners wanted nothing to do with us.
Stayed 2 nights in Jul 2025

2/10 Terrible

Kenneth

No place to park
Stayed 1 night in Jul 2025

8/10 Good

Susan, South Bend

Travelled with group
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

10/10 Excellent

Jeremy

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Jul 2025

10/10 Excellent

Steve, Hopkins

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Above a pizza place with great specials offered and the decor was a mix of what looked like a different decor for each room
Stayed 1 night in Jul 2025

8/10 Good

TAMI, IOWA CITY

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was hard to find. The room was very small but clean.
Stayed 2 nights in Jul 2025

10/10 Excellent

Geoffrey

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

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!
Stayed 2 nights in Jul 2025

10/10 Excellent

Verified traveller

Travelled with group
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

8/10 Good

Jenny

Business traveller
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Jun 2025