Dorothy's

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

VIP Access

Choose dates to view prices

Where to?

Dates

January 2026

February 2026

Full-size fridge, microwave, toaster oven, cookware/dishes/utensils

Overview
Rooms
Location
Policies

Very good

Popular amenities

Pet friendly
Free WiFi
Air conditioning
Laundry
Kitchen

Explore the area

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

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 Access

Room options

Basic Single Room

Wonderful

54 sq ft
Sleeps 2
1 Double Bed

Economy Single Room

50 sq ft
Sleeps 2
1 Queen Bed

Standard Single Room

Sleeps 2
1 Double Bed

City Single Room

50 sq ft
Sleeps 2
1 Queen Bed

Standard Studio

Wonderful

Sleeps 2
1 Queen Bed

Basic Apartment

1197 sq ft
4 bedrooms
Sleeps 9
2 Queen Beds, 2 Double Beds and 1 Twin Sofa Bed

City Apartment

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

About the neighborhood

Chicago

Located in Lakeview within a short walk of Wrigley Field, Dorothy's is within a mile (2 km) of other popular sights such as 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 Chicago

What's nearby

Lincoln Park - 8 min walk - 0.5 miles
Wrigley Field - 8 min walk - 0.5 miles
Vic Theatre - 9 min walk - 0.5 miles
Briar Street Theatre - 9 min walk - 0.5 miles
Advocate Illinois Masonic Medical Center - 14 min walk - 0.8 miles

Getting around

Chicago Clybourn 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

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 communal living room.

Guests can expect to find free WiFi. Other amenities include refrigerators, microwaves, and hair dryers. Housekeeping is available on request.

Similar properties

Pet friendly
Parking included
Free WiFi

$73 nightly

Jan 6 - Jan 7

Total with taxes and fees

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

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

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 16 minutes on foot from Lake Michigan. You'll also find Michigan Avenue and Chicago Riverwalk within a short drive.

Is parking available on site 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 a good place to stay for couples?

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

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 17.5 mi away (45 minutes by car). Another top airport is Chicago O'Hare Intl. Airport (ORD), which is located 16.6 mi away (48-minute drive).

Are there rooms with balconies that I can book at Dorothy's?

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

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

10/10 Excellent

Mark

Dec 31, 2025

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

Joshua

Traveled with group

Oct 2, 2025

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

Sep 26, 2025

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

Stayed 1 night in Sep 2025

10/10 Excellent

Gina

Traveled with pets

Sep 25, 2025

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

Sep 22, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Stayed 2 nights in Sep 2025

10/10 Excellent

Fabiola

Sep 21, 2025

Stayed 2 nights in Aug 2025

8/10 Good

Missy

Traveled with partner

Sep 18, 2025

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

Sep 18, 2025

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

Sep 18, 2025

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

Stayed 1 night in Sep 2025

4/10 Poor

Justin

Sep 15, 2025

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

Sep 9, 2025

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

Sep 9, 2025

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

Sep 7, 2025

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

Sep 3, 2025

Liked: Cleanliness, amenities

Clean room beautiful.yards convenient

Stayed 2 nights in Aug 2025

10/10 Excellent

Lisa

Traveled with pets

Aug 27, 2025

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 traveler

Aug 25, 2025

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

Aug 20, 2025

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

Aug 15, 2025

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

Stayed 4 nights in Aug 2025

10/10 Excellent

Connor

Aug 11, 2025

Stayed 3 nights in Jul 2025

4/10 Poor

John

Aug 8, 2025

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

Stayed 1 night in Aug 2025

4/10 Poor

Gary

Aug 8, 2025

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

Traveled with group

Aug 7, 2025

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

Traveled with family

Aug 7, 2025

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

Traveled with family

Aug 3, 2025

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

Stayed 1 night in Aug 2025

10/10 Excellent

Colin

Jul 28, 2025

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

Dorothy's

Choose dates to view prices

Photo gallery for Dorothy's

Reviews

Popular amenities

Explore the area

Room options

View all photos for Basic Single Room

Basic Single Room

View all photos for Economy Single Room

Economy Single Room

View all photos for Standard Single Room

Standard Single Room

View all photos for City Single Room

City Single Room

View all photos for Standard Studio

Standard Studio

View all photos for Basic Apartment

Basic Apartment

View all photos for City Apartment

City Apartment

You may also like

Best Western Plus Hawthorne Terrace Hotel

About the neighborhood

Chicago

What's nearby

Getting around

Restaurants

About this property

Dorothy's

Similar properties

The Villa Toscana

Property amenities

Internet

Parking and transportation

Food and drink

Things to do

Family friendly

Conveniences

Guest services

Accessibility

More

Room amenities

Bedroom

Bathroom

Food and drink

More

Policies

Check-in

Check-out

Special check-in instructions

Access methods

Pets

Property payment types

Important information

Optional extras

You need to know

We should mention

Property is also known as

Frequently asked questions

Dorothy's Reviews

Reviews

Very Good

8.8/10

8.0/10

8.6/10

8.4/10

8.6/10

Reviews

10/10 Excellent

Mark

Mark

8/10 Good

Joshua

Joshua

10/10 Excellent

Brian

Brian

10/10 Excellent

Gina