Find the Best Southwest Side Bed and Breakfast

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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Southwest Side B&B

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.6 out of 10, Excellent, (48)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
The price is £92
includes taxes & fees
30 Jun - 1 Jul
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (573)
"Was a great stay!"
The price is £78
includes taxes & fees
30 Jun - 1 Jul
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (361)
"Breakfast was great, the staff was kind, and it was a pleasant surprise. "
The price is £139
includes taxes & fees
30 Jun - 1 Jul
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (463)
"Excellent location. Beautiful property, extremely clean."
The price is £128
includes taxes & fees
30 Jun - 1 Jul
The Sono Chicago
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (474)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is £144
includes taxes & fees
7 Jul - 8 Jul
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
The price is £219
includes taxes & fees
7 Jul - 8 Jul
Harvey House Bed & Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (177)
"Incredible service, amazing breakfast and gorgeous rooms."
The price is £168
includes taxes & fees
27 Jul - 28 Jul
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (247)
"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 £255
includes taxes & fees
1 Jul - 2 Jul
Wicker Park Inn
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, (137)
"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 D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (103)
"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"
The price is £225
includes taxes & fees
8 Jul - 9 Jul
Villa D' Citta
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 £138
includes taxes & fees
30 Jun - 1 Jul
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 £138
includes taxes & fees
30 Jun - 1 Jul
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is £138
includes taxes & fees
30 Jun - 1 Jul
Dubois Guest House Room 101
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is £138
includes taxes & fees
30 Jun - 1 Jul
Villa Dubois Guest House Room 4
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is £138
includes taxes & fees
30 Jun - 1 Jul
Villa Dubois Guest Room 6
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is £138
includes taxes & fees
30 Jun - 1 Jul
Dubois Guest House Room 202
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is £209
includes taxes & fees
1 Jul - 2 Jul
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is £150
includes taxes & fees
30 Jun - 1 Jul
Dubois Guest House Room 203
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is £185
includes taxes & fees
30 Jun - 1 Jul
Wrigleyville Suites Room 2
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is £150
includes taxes & fees
30 Jun - 1 Jul
Villa Dubois Guest House Room 1
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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