See all properties

Dorothy's

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

Choose dates to view prices

Photo gallery for Dorothy's

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

Reviews

8.4 out of 10
Very good

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Laundry
  • Kitchen

Explore the area

View in a map
3445 N Halsted St, Chicago, IL, 60657
  • Place, Wrigley Field
    ‪6 min walk‬
  • Place, Vic Theatre
    ‪9 min walk‬
  • Place, Lincoln Park
    ‪9 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪23 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
Learn more about VIP AccessOpens in a new window

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

  • 50 sq ft
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Single Room

Free WiFi, bed sheets

Standard Single Room

  • 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

9.6 out of 10
Exceptional
(4 reviews)
  • 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

You may also like

Ad
Lobby sitting area

The Chicago Hotel Collection - Wrigleyville

Lakeview
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
7.0 out of 10, Good, 965 reviews
$113 nightly
The price is $133
Feb 25 - Feb 26
Total with taxes and fees
The Chicago Hotel Collection - Wrigleyville

About the neighborhood

Chicago

Located in Lakeview, Dorothy's is a leisurely stroll from popular sights such as Wrigley Field and Lake Michigan. The 7 rooms at this 3-star bed & breakfast include refrigerators and microwaves and guests can enjoy free breakfast.
View more B&B in ChicagoOpens in a new window

What's nearby

  • Wrigley Field - 6 min walk - 0.4 miles
  • Vic Theatre - 9 min walk - 0.5 miles
  • Lincoln Park - 9 min walk - 0.5 miles
  • Wrigley View Rooftop - 11 min walk - 0.6 miles
  • Theater Wit - 14 min walk - 0.8 miles

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
  • ‪Progress Bar Chicago - ‬2 min walk
  • ‪Las Mañanitas - ‬2 min walk

About this property

Dorothy's

Bed & breakfast with free breakfast, 9-minute walk to Wrigley Field
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 laundry facilities, local meal delivery service, and a TV in a common area.
Guests can expect to find free WiFi. Other amenities include refrigerators, microwaves, and hair dryers. Housekeeping is available on request.

Similar properties

Double Room, Private Bathroom (Venetian) | Terrace/patio
The Villa Toscana
  • Pet friendly
  • Parking included
  • Free WiFi
7.8 out of 10, Good, 629 reviews
$76 nightly
The price is $83
Feb 11 - Feb 12
Total with taxes and fees
The Villa Toscana

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 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) (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

  • 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 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
  • 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. 

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 Feb 8, 2026, prices found for a 1-night stay for 2 adults at Dorothy's on Feb 16, 2026 start from $34.89, excluding 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 nearby.

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.

Is Dorothy's good for couples?

Amenities at this bed u0026 breakfast that appeal to couples include a meal delivery service and free breakfast.

Are there hot tubs at Dorothy's?

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?

No, there aren't connecting guestrooms at this bed & breakfast.

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).

Can I book a room with a balcony at Dorothy's?

No, there aren't any guestrooms with balconies at Dorothy's.

Dorothy's Reviews

Reviews

8.4

Very Good

Rating 10 - Excellent. 57 out of 105 reviews
Rating 8 - Good. 27 out of 105 reviews
Rating 6 - Okay. 8 out of 105 reviews
Rating 4 - Poor. 7 out of 105 reviews
Rating 2 - Terrible. 6 out of 105 reviews

8.8/10

Cleanliness

8.0/10

Staff & service

8.6/10

Amenities

8.6/10

Property conditions & facilities

Reviews

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

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

8/10 Good

Steve

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
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.
Stayed 1 night in Oct 2025

8/10 Good

Lisa

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Halsted is a nice neibourhood. We liked the secondhand shops.
Stayed 3 nights in Oct 2025

4/10 Poor

Troy

Disliked: Cleanliness, property conditions & facilities
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.
Stayed 1 night in Oct 2025

10/10 Excellent

Thomas

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

8/10 Good

Joshua

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
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.
Stayed 4 nights in Aug 2025

10/10 Excellent

Brian

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

10/10 Excellent

Gina

Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 1 night in Sep 2025

10/10 Excellent

Donovan

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

10/10 Excellent

Fabiola

Stayed 2 nights in Aug 2025

8/10 Good

Missy

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
I liked the little area it was in and how homey it felt, however the parking was a nightmare. You are given a parking pass, but it’s almost pointless if you can’t find a spot. After over an hour of trying to find parking, we still had to get up at 7am to find parking again since it was a tow zone at that time. When looking for help on what the signs meant (we are new to the area), the staff we messaged for help was passive-aggressive. If you ignore all that, then it was plenty fine.
Stayed 2 nights in Sep 2025

10/10 Excellent

Kenneth

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
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!
Stayed 3 nights in Sep 2025

8/10 Good

Mark

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

4/10 Poor

Justin

Disliked: Cleanliness, staff & service, room comfort

Cheap hostel, fine if that’s your jam

THIS IS NOT A HOTEL. It’s not even a “Bed and Breakfast.” It’s a hostel made by taking a large apartment, filling it with secondhand mismatched furniture, and adding smart locks to the doors. 2 bathrooms are shared among everybody, along with a small kitchen and living/dining room. It’s completely unstaffed, and there’s a sign stating that if you want food, you can go to the pizza place downstairs. With that in mind, it’s mostly fine. The bed gets the job done. The cramped small room has only a TV and a small end table. The AC is cranked up high, and the extra blankets are all very stained and have holes. This was not properly listed and when I saw the owner there I mentioned that there was no mention of shared bathrooms. She got very defensive. Not a pleasant interaction. Not recommended unless it’s really cheap.
Stayed 2 nights in Sep 2025

10/10 Excellent

Rae

Traveled 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

Traveled 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