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Find a Bed and Breakfast in Southwest Side from CA $97

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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

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 CA $41
CA $97 total
includes taxes & fees
Dec 7 - Dec 8
Dorothy's
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
9.8 out of 10, Exceptional, (574 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 CA $186
CA $219 total
includes taxes & fees
Nov 23 - Nov 24
The Sono Chicago
A narrow stone pathway leading to a house with a green porch and a large tree overhanging the path.

3. 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 CA $66
CA $134 total
includes taxes & fees
Nov 10 - Nov 11
The Villa Toscana
A patio with a grill, outdoor seating, and potted plants.

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (423 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is CA $261
CA $295 total
includes taxes & fees
Nov 11 - Nov 12
Ray's Bucktown B&B
A courtyard with brick arches, outdoor seating, and potted plants.

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 CA $291
CA $341 total
includes taxes & fees
Dec 2 - Dec 3
Villa D' Citta
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

6. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (222 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
The price is CA $369
CA $417 total
includes taxes & fees
Dec 10 - Dec 11
The Publishing House B&B
A brick building with a round metal table and chairs, a blue door, and a small garden area with plants and a bench.

7. 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 CA $296
CA $347 total
includes taxes & fees
Nov 16 - Nov 17
Wicker Park Inn
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

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 CA $365
CA $405 total
includes taxes & fees
Nov 10 - Nov 11
Harvey House Bed & Breakfast
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

9. 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 CA $161
CA $275 total
includes taxes & fees
Nov 10 - Nov 11
House 5863 - Chicago Bed and Breakfast
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $343
CA $378 total
includes taxes & fees
Nov 30 - Dec 1
Pristine Apartment with Free Street Parking
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.
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Top Southwest Side Hotel Reviews

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"N/A"
Krisanne 1-night trip
Posted 1 hour ago
Sports Illustrated Resorts Chicago

Find out more about Southwest Side

Southwest Side B&B information

Number of reviews
2,402
Accommodation
10 B&B
Lowest Price
CA $97
Highest Price
CA $448

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