Photo by by Midway Intl Airport

Search B&B in Southwest Side

  • 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
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Southwest Side bed & breakfast

A narrow stone pathway leading to a house with a green porch and a large tree overhanging the path.

1. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.2 out of 10, Very good, (690 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is P2,308
P5,259 total
includes taxes & fees
Nov 24 - Nov 25
The Villa Toscana
A kitchen with a dining table set for a meal, a dog sitting at the table, and various kitchen appliances and utensils.

2. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (197 reviews)
"I enjoyed my stay"
United States
Kellen
The price is P1,695
P4,220 total
includes taxes & fees
Dec 14 - Dec 15
Dorothy's
A multi-story building with a brick facade, a central entrance with an archway, and a small balcony on the second floor.

3. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
9.8 out of 10, Exceptional, (575 reviews)
"I like that it had a balcony food choice wasn’t my type of style end up ordering food off of site but definitely had all the amenities for you to be ready for the next day. Will be staying again little bit pricey for a short weekend stay but I will definitely be coming back. Very great part of the town hope to own my own own home in this place one day."
United States
Tavarion
The price is P8,794
P10,323 total
includes taxes & fees
Nov 23 - Nov 24
The Sono Chicago
A building with a large window, a bench, and a sign that reads "RAY'S BUCKTOWN BED & BREAKFAST".

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (424 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is P13,076
P14,761 total
includes taxes & fees
Nov 16 - Nov 17
Ray's Bucktown B&B
A gated entrance with a stone pillar, a sign, and a staircase leading to a building with arched windows and a wrought iron gate.

5. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (129 reviews)
"Very elegant !"
United States
Hernando
The price is P13,118
P15,399 total
includes taxes & fees
Dec 1 - Dec 2
Villa D' Citta
A dark blue door with a small window above it, flanked by two potted plants.

6. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (287 reviews)
"Loved the location"
United States
Mary
The price is P12,777
P14,999 total
includes taxes & fees
Nov 16 - Nov 17
Wicker Park Inn
A modern brick building with large windows, a covered entrance, and a tree-lined street.

7. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (525 reviews)
"Honestly great, clean, and did not hear neighbors. Would stay again!"
United States
Malena
The price is P7,265
P12,406 total
includes taxes & fees
Nov 16 - Nov 17
House 5863 - Chicago Bed and Breakfast
A spacious living room with a fireplace, a piano, and a dining area with a table and chairs.

8. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (138 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is P16,449
P18,255 total
includes taxes & fees
Nov 16 - Nov 17
Harvey House Bed & Breakfast
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

9. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (226 reviews)
"This bed and breakfast is incredibly charming and close to my favorite restaurants in Chicago. I will be back!"
United States
Tina
The price is P18,296
P20,654 total
includes taxes & fees
Nov 29 - Nov 30
The Publishing House B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side
An airport with multiple runways, parked airplanes, and a large terminal building.
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport