Dorothy's

Bed and breakfast3445 North Halsted Street, Chicago, IL, United StatesShow on map

You won’t be charged yet

7.9 · Good67 reviews

Check-in from 4:00 PMCheck-out by 12:00 PM.
Superb locationGuests rate the location 9.1 out of 10, at 3445 North Halsted Street.

Location and Nearby Attractions Centrally located in Chicago, within walking distance to Wrigley Field and a short drive to Lincoln Park Zoo, our four-bedroom apartment is the perfect base to explore the city.

Comfort and Convenience Featuring air conditioning, free WiFi, and a fully equipped kitchen, our spacious bed and breakfast offers a comfortable and convenient stay for guests.

Local Landmarks and Accessibility Within reach of popular landmarks like 360 Chicago and Water Tower Chicago, with easy access to transportation links including Midway International Airport, make your stay at Four bedroom apartment unforgettable.

Book now to experience the best of Chicago!

What this place offers

WiFi available
Free WiFi
Parking
Free Parking
Non-smoking rooms
Air conditioning
Room service
Heating
Pets allowed
Luggage storage

Rooms

7.9

Good

Rated 7.9 out of 10 by 67 guests who stayed here.

Cleanliness7.6
Service8.1
Location9.1
Rooms7.0
Amenities8.1
Value8.5
Food & drink7.6

Guests mention

Great locationClean rooms

MichaelUnited States
September 2026Solo traveller
Fantastic Stay
This place is amazing! It's located in a gay Chicago Neighborhood that is super friendly and clean. The building is super historic and the room was fantastic. They have everything covered. I felt at home and loved…
JulieUnited States
August 2026Solo traveller
Great location, clean, well kept - the neighborhood is great.
Nice old house in a beautiful location. Beautiful bathrooms, nice kitchen, charming vibe
Confusing to access at first- check in and instructions were lengthy - but once in it was easy in and out. Quiet and cozy rooms.
ElaineUnited States
July 2026Solo traveller
Affordable clean and safe accommodation
Clean, quiet and comfortable
No bin in room and no basket for used small towels
Rafael DecioBrazil
July 2026Couple
The bed was good
I found it very difficult to get in, the host was not patient
OscarBelgium
June 2026Solo traveller
Aventura
La ubicacion.
Un gatito muy hermoso entró un rato a la sala.
El pomo de la ducha uno de los baños no funcionó. Tuve que ir a la siguiente ducha.
SpencerUnited States
June 2026Couple
Friends weekend trip to Chicago. Dorthy’s was a highlight.
Location and cute facility. We loved the breakfast area in the home next door. Online check in was straightforward and very well organized.
Nothing

Reviews are written by guests who booked through our supplier and stayed, shown as written and in their own language. Category scores are the supplier’s reading of recent reviews, updated January 2026.

Where you’ll be

3445 North Halsted Street, Chicago, IL, United States

Guests rate the location 9.1 out of 10 — superb.

Things to know

Cancellation

Each room shows its own terms before you pay.

Most rates can be cancelled free until a date shown on the room.

Non-refundable rates are marked as such.

House rules

Check-in from 4:00 PM until 10:00 PM

Check-out by 12:00 PM

No children

Pets allowed on request; charges may apply

Non-smoking rooms available

There is no front desk at this property. Prior to arrival, guests must complete online registration with the property via a secure link. Guests will be asked to provide the property with a copy of their government-issued photo ID before arrival. If you are planning to arrive after 10:00 PM please contact the property in advance using the information on the booking confirmation. Guests planning to arrive outside of normal check-in hours will receive an email with check-in instructions and an access code. Guests can access their accommodation through a private entrance. A virtual front desk provides assistance to guests.

Pets. Service animals are exempt from fees/restrictions

Children and extra beds. No rollaway/extra beds available

Accessibility. No elevators

Pets. Pets allowed

General. Professional property host/manager

Children and extra beds. No cribs (infant beds) available

Pets. Service animals are allowed

Payment & property

Paid when you book, not at the desk.

Rates include the taxes and fees we can read.

The property may take a card at check-in for incidentals.

Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. This property does not accommodate bachelor(ette) or similar parties. Managed by a private host A deposit may be required at the property.

What we’d check for you here

The pet fee and any size limit, which is where these bookings usually come apart.
Whether there is room for a pickup, a trailer or a van, not just a car.
Whether the rate moves for your dates, and what it includes.
What the property actually charges at the desk on top of the rate.

Questions about Dorothy's

What time is check-in and check-out at Dorothy's?

Check-in is from 4:00 PM. Check-out is by 12:00 PM. If you're arriving late, tell us and we'll ask the property to hold the room.

Does Dorothy's allow pets?

Yes — the property states that pets are allowed. Size, number and fee are set by the property rather than by us, so say you're bringing a pet when you book and we'll confirm the terms before anything is charged.

Is there parking at Dorothy's?

Parking is listed among the property's facilities. Whether it's free and whether a space can be reserved varies, so we check it against your dates rather than promise it here.

Does Dorothy's have Wi-Fi?

Yes — internet access is listed among the property's facilities.

How do I book Dorothy's?

Put your dates in above and book online, or call (888) 789-8585 and we'll do it for you — including things a booking form can't handle, like a block of rooms, a monthly rate or an invoice for your employer.

Where is Dorothy's?

3445 North Halsted Street, Chicago, IL.

Other places we book in Chicago

Nothing to do with the booking above. The same market, priced the same way, for if this one is not it.

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