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Dorothy's

2.0 star property
VIP Access

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Photo gallery for Dorothy's

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

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Kitchen

Explore the area

View in a map
3445 N Halsted St, Chicago, IL, 60657
  • Place, Lincoln Park
    ‪8 min walk‬
  • Place, Wrigley Field
    ‪8 min walk‬
  • Place, Vic Theatre
    ‪11 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪32 min drive‬
VIP Access
Curated for quality and service, VIP Access stays consistently receive our highest guest ratings.
  • Expect exceptional service
  • Extra savings and perks for Rewards members
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Room options

View all photos for Basic Single Room

Free WiFi, bed sheets

Basic Single Room

9.0 out of 10
Wonderful
(4 reviews)
  • 54 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for Economy Single Room

Free WiFi, bed sheets

Economy Single Room

10.0 out of 10
Exceptional
(1 review)
  • 50 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

7.0 out of 10
Good
(4 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for City Single Room

Free WiFi, bed sheets

City Single Room

  • 50 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Studio

Free WiFi, bed sheets

Standard Studio

9.8 out of 10
Exceptional
(6 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Basic Apartment

Free WiFi, bed sheets

Basic Apartment

  • 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

  • 5 bedrooms
  • Sleeps 11
  • 3 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

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About the neighborhood

Chicago

Located in Lakeview, Dorothy's is a leisurely stroll from popular sights such as Wrigley Field and Lake Michigan. This 7-room bed & breakfast welcomes guests with conveniences like free breakfast, free in-room WiFi, and a microwave in a common area.
View more B&B in ChicagoOpens in a new window

What's nearby

  • Lincoln Park - 8 min walk - 0.5 miles
  • 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 - ‬2 min walk
  • ‪Roscoe's - ‬2 min walk
  • ‪Hydrate - ‬1 min walk
  • ‪Replay Lakeview - ‬1 min walk
  • ‪The Chicago Diner - ‬1 min walk

About this property

Dorothy's

Guests of Dorothy's enjoy access to free WiFi in public areas, microwave in a common area, and refrigerator in a common area. If you plan to drive, free offsite parking is available. Friendly staff can provide luggage storage, and also offer advice about sightseeing. Additional amenities include local meal delivery service and a communal living room.
Guests can expect to find free WiFi. Other amenities include microwaves, hair dryers, and local meal delivery service. Housekeeping is available on request.

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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

  • This property welcomes pets for USD 25 per pet, per stay
  • Service animals exempt from fees

Property payment types

Important information

Optional extras

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

  • 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

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4:00 PM
  • Check-out: noon
  • Minimum check-in age: 18
Driving? This property offers free nearby parking.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards and debit cards. Cash is not accepted. 
  • Onsite safety features include a fire extinguisher.

Additional information about polices, regulations, and more:

  • There are no elevators.
  • No cribs or infant beds are available.
  • No rollaway or extra beds are available.

Property is also known as

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

Frequently asked questions

What's there to do around Dorothy's?

This bed & breakfast is situated in Lakeview within a short 9-minute walk of Wrigley Field and also 15 minutes on foot from Lake Michigan. You'll also find Michigan Avenue and Chicago Riverwalk within a short drive.

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

As of May 15, 2026, prices found for a 1-night stay for 2 adults at Dorothy's on May 26, 2026 start from $121, 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.

Is there parking available at Dorothy's?

No, there isn't parking at the bed & breakfast but you'll find free parking.

Does Dorothy's feature a casino at the property?

No, Dorothy's doesn't have a casino.

Will I find an indoor pool at Dorothy's?

No, there is no indoor pool at this bed & breakfast.

What amenities will couples enjoy at Dorothy's?

Amenities at this bed & breakfast that appeal to couples include meal delivery service and a free daily breakfast.

Does Dorothy's have a hot tub?

No, there isn't a spa tub at this bed & breakfast.

Does Dorothy's have a restaurant that serves breakfast?

Dorothy's offers free continental breakfast each morning though there is no restaurant.

Will Dorothy's allow pets to stay for free?

Although they can't stay for free, pets are welcome at Dorothy's for a fee of USD 25 per pet, per stay.

Does Dorothy's have connecting rooms available?

No, this bed & breakfast doesn't feature connecting guestrooms.

What is the closest airport to Dorothy's?

The closest major airport to Dorothy's is Chicago Midway Airport (MDW), which is 17.3 mi away (48 minutes by car). Another top airport is Chicago O'Hare Intl. Airport (ORD), which is located 15.8 mi away (45-minute drive).

Are there rooms with balconies at Dorothy's?

No, you won't find guestrooms with balconies at Dorothy's.

Dorothy's Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 74 out of 126 reviews
Rating 8 - Good. 31 out of 126 reviews
Rating 6 - Okay. 8 out of 126 reviews
Rating 4 - Poor. 7 out of 126 reviews
Rating 2 - Terrible. 6 out of 126 reviews

9.0/10

Cleanliness

8.2/10

Staff & service

8.8/10

Amenities

8.6/10

Property conditions & facilities

Reviews

8/10 Good

stan

Liked: Cleanliness, amenities, property conditions & facilities
Inexpensive place for Chicago.
Stayed 1 night in Apr 2026

8/10 Good

Sam

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I would stay here again. Check-in comes with very detailed instructions, and it was a breeze– easy, straightforward. The unit was kept exceptionally clean, the kitchen is pretty well-stocked for anything you might want to make, the breakfast is a great way to start each day on time, and the availability of a parking permit is wonderful. The proximity to the best bars is unmatched, and you’re on the third floor, so the street noise isn’t even that bad. My only negative marks are that there are only two bathrooms for what could be up to 8 people, the water pressure is not great, and for some reason, the climate control was set to “Fire & Brimestone” for the duration of our stay, so we had to keep the window open. Otherwise, all top marks.
Stayed 2 nights in Apr 2026

10/10 Excellent

Kimberly

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the place. Has everything I needed.
Stayed 2 nights in Mar 2026

10/10 Excellent

David

Liked: Cleanliness, staff & service
All as promised
Stayed 2 nights in Feb 2026

10/10 Excellent

Jace

Stayed 1 night in Jan 2026

10/10 Excellent

Jennifer

Liked: Cleanliness, amenities, property conditions & facilities
Fantastic location within walking distance of Wrigley Field and many Lakeview hot spots. Check-in and check-out were seamless, and I was pleasantly surprised by the amount of space within the suite! It's definitely not for folks who aren't used to urban street noise, although it didn't bother me at all. My ONLY "complaint" was that the room was super cold. There is a portable radiator in the living room, but even turned up all the way, it didn't warm the space up at all. I located an extra blanket in the front closet, wrapped up in that, and was warm and happy as a clam. I will definitely be returning!
Stayed 1 night in Jan 2026

10/10 Excellent

Winter Fox, Shasta Lake

Liked: Cleanliness, property conditions & facilities
cozy and close to cool places
Stayed 2 nights in Jan 2026

8/10 Good

Erica

Liked: Cleanliness, property conditions & facilities
Automated check-in worked well, waffles were great
Stayed 2 nights in Jan 2026

10/10 Excellent

Yesim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was nicee
Stayed 2 nights in Jan 2026

10/10 Excellent

Mark

Liked: Cleanliness, amenities, property conditions & facilities
The room was small, but very comfortable. Initially, I was a bit leery of the "no reception; we'll send you a code" check-in, but it went very smoothly. The code worked on all the doors it was supposed to work on, and I appreciated the triple-layer of code security - outside door, door to the floor, door to the room. Dorothy's is ideally situated, and easy walking distance to attractions in the area, in addition to the Red line train and numerous bus lines. If I had to ding Dorothy's on anything, it's this: Coffeemate isn't cream and doesn't do the same in your coffee in the morning as does half-and-half.
Stayed 3 nights in Dec 2025

8/10 Good

Janne

Stayed 4 nights in Dec 2025

10/10 Excellent

lashonte

Stayed 2 nights in Dec 2025

10/10 Excellent

James

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
What an absolutely amazing room, made me feel like home. Wonderful apartment in the middle of everything.
Stayed 1 night in Dec 2025

8/10 Good

David

Stayed 1 night in Dec 2025

8/10 Good

Konrad

Liked: Cleanliness, staff & service, amenities
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.
Stayed 3 nights in Nov 2025

10/10 Excellent

bijan

Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
so convenient, cozy, and welcoming. excellent
Stayed 3 nights in Nov 2025

2/10 Terrible

Kathy

Traveled with family and small children
Disliked: Cleanliness, amenities, property conditions & facilities
Absolutely disgusting
Stayed 1 night in Nov 2025

10/10 Excellent

ROMEO

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun place
Stayed 3 nights in Nov 2025

8/10 Good

Sean

Liked: Cleanliness, staff & service, amenities
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.
Stayed 1 night in Nov 2025

4/10 Poor

John

Disliked: Cleanliness
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.
Stayed 1 night in Nov 2025

10/10 Excellent

Fernando Emmanuel

Liked: Cleanliness, staff & service, property conditions & facilities
Just breakfast no good… noise but I was advised, everything else is perfect!
Stayed 4 nights in Nov 2025

8/10 Good

Doug

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Shower water was cool so I expedited a clean up only.
Stayed 1 night in Oct 2025

10/10 Excellent

Zac

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice location to wrigleyville
Stayed 1 night in Sep 2025

10/10 Excellent

Vincient, KANSAS CITY

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 2 nights in Oct 2025

10/10 Excellent

Ashley

Liked: Cleanliness, property conditions & facilities
Can’t beat the price or location. Everything seemed clean and I loved the waffles.
Stayed 1 night in Oct 2025