Find a Bed and Breakfast in Southwest Side from CA $112

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Southwest Side B&B

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very good, (58)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
The price is CA $160
CA $236 total
includes taxes & fees
Aug 6 - Aug 7
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (588)
"Was a great stay!"
The price is CA $117
CA $192 total
includes taxes & fees
Aug 6 - Aug 7
The Villa Toscana
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (476)
"Everything was taken care of! A wonderful stay. "
The price is CA $182
CA $291 total
includes taxes & fees
Aug 11 - Aug 12
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (369)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is CA $240
CA $271 total
includes taxes & fees
Aug 6 - Aug 7
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (249)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
The price is CA $298
CA $350 total
includes taxes & fees
Sep 2 - Sep 3
Wicker Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
The price is CA $225
CA $264 total
includes taxes & fees
Aug 6 - Aug 7
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is CA $218
CA $246 total
includes taxes & fees
Sep 4 - Sep 5
The Publishing House B&B
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (114)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is CA $361
CA $413 total
includes taxes & fees
Aug 11 - Aug 12
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
The price is CA $394
CA $463 total
includes taxes & fees
Aug 11 - Aug 12
Villa D' Citta
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (141)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is CA $186
CA $328 total
includes taxes & fees
Aug 10 - Aug 11
Villa Dubois Guest Room 6
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is CA $130
CA $259 total
includes taxes & fees
Aug 7 - Aug 8
Dubois Guest House Room 101
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is CA $130
CA $259 total
includes taxes & fees
Aug 7 - Aug 8
Dubois Guest House Room 201
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is CA $112
CA $237 total
includes taxes & fees
Aug 7 - Aug 8
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is CA $232
CA $399 total
includes taxes & fees
Aug 18 - Aug 19
Villa Dubois Guest House Room 2
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
The price is CA $112
CA $237 total
includes taxes & fees
Aug 7 - Aug 8
Dubois Guest House Room 202
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is CA $130
CA $259 total
includes taxes & fees
Aug 7 - Aug 8
Villa Dubois Guest House Room 1
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is CA $1,303
CA $2,038 total
includes taxes & fees
Aug 12 - Aug 13
Five bedroom - 3 bath - Sleeps 12
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Very good overall "
Shawn P 5-night trip
Posted 5 hours ago
InterContinental Chicago Magnificent Mile by IHG