Southwest Side B&B

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Southwest Side bed & breakfast

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

1. Dorothy's

Lakeview

Steven

P6,613 total

includes taxes & fees

Oct 26 - Oct 27

A bathroom with a glass-tiled wall, a sink, and a shower area.

2. Ray's Bucktown B&B

Bucktown

Susan

P13,420 total

includes taxes & fees

Oct 1 - Oct 2

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

3. The Sono Chicago

Near North Side

Christie

P20,044 total

includes taxes & fees

Oct 1 - Oct 2

A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

4. The Villa Toscana

Lakeview

John

P7,473 total

includes taxes & fees

Oct 5 - Oct 6

A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

5. The Publishing House B&B

Downtown Chicago

Kathryn

P17,545 total

includes taxes & fees

Oct 25 - Oct 26

A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

6. Harvey House Bed & Breakfast

Oak Park

Monica

P20,316 total

includes taxes & fees

Oct 13 - Oct 14

A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

7. House 5863 - Chicago Bed and Breakfast

Edgewater

jiantao

P13,110 total

includes taxes & fees

Oct 6 - Oct 7

A grand foyer with a wooden staircase, a chandelier, and a large window.

8. Villa D' Citta

Lincoln Park

Jeffrey

P18,502 total

includes taxes & fees

Oct 7 - Oct 8

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Side Hotel Reviews

Hilton Chicago

8/10 Good

"It was a very nice place and we had an amazing time"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"We enjoyed our stay and first visit to Chicago. All the staff were very helpful except one young lady at desk unable to help us with questions about the L train and told us to use our phones. We are an older couple 76& 80 and would have appreciated some assistance."

Hotel Saint Clair- Magnificent Mile

8/10 Good

"The room we were assigned had a wheelchair accessible bathroom which was very large took up a considerable amount of space in the room. We could barely walk around the bed, and there were no chairs nor a small desk or table. I’m not sure why we were assigned a room designed for wheelchairs, because we didn’t request any special accommodations. I’m sure they would have moved us if we had asked, but we really didn’t spend much time in the room other than to sleep. The room and bathroom were very clean and everything was working properly. The location was outstanding. We would definitely stay there again."

River Hotel

8/10 Good

"The staff at this hotel were all very friendly and helpful. I requested extra coffee and other supplies for the room several times and they never failed to bring it to our room promptly. I did think the interior of our room was a bit outdated and could use some updating. The furniture, carpet, and bathroom all had a very old look and definitely needed updating badly. That was very minor though. Overall we enjoyed our stay very much. There were some loud motorcycles and cars every night that insisted on constantly revving their engines around 11pm-12am which was annoying. Not the fault of the property at all, but definitely something to be aware of if you’re wanting a more quiet atmosphere."

Find out more about Southwest Side