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Find a Bed and Breakfast in South Side from CA $194

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for South Side bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (529 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is CA $257
CA $302 total
includes taxes & fees
Jul 28 - Jul 29
The Sono Chicago
Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (208 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is CA $375
CA $424 total
includes taxes & fees
Aug 4 - Aug 5
The Publishing House B&B
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (149 reviews)
"Very clean and within walking distance to Wrigley Field..."
United States
Robert
The price is CA $124
CA $194 total
includes taxes & fees
Aug 11 - Aug 12
Dorothy's
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (407 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is CA $303
CA $342 total
includes taxes & fees
Jul 27 - Jul 28
Ray's Bucktown B&B
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (129 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
The price is CA $380
CA $422 total
includes taxes & fees
Jul 20 - Jul 21
Harvey House Bed & Breakfast
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (659 reviews)
"Clean room, self serve breakfast, free street parking permit, cute cats!"
United States
Shu-Ting
The price is CA $153
CA $236 total
includes taxes & fees
Jul 19 - Jul 20
The Villa Toscana
Presidential Studio Suite, 2 Bedrooms (1st Floor) | Living area

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (508 reviews)
"The place is well run. The communal areas are clean and have what you need. The neighborhood is nice, everyone i took was gorgeous! And the perfect distance from the city."
United States
Joanna
The price is CA $184
CA $303 total
includes taxes & fees
Jul 27 - Jul 28
House 5863 - Chicago Bed and Breakfast
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (273 reviews)
"Nice place to stay in an historic neighborhood"
United States
Linda
The price is CA $351
CA $412 total
includes taxes & fees
Aug 11 - Aug 12
Wicker Park Inn
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (121 reviews)
"A fantastic stay yet again. I have stayed here the last few years while attending a conference. All the staff were great and amazing selection of food for breakfast and for late night snacks. I will be back again next year"
United Kingdom
Robert
The price is CA $370
CA $434 total
includes taxes & fees
Jul 28 - Jul 29
Villa D' Citta
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 South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good
"The room was clean and the bed and pillows were comfortable. The shower was nice and the staff was professional and helpful. The one thing I didn’t like was having to pay for parking, other than that it was good."
Roosevelt 4-night trip
Posted 1 hour ago
Holiday Inn Chicago – Midway Airport S by IHG

Find out more about South Side

South Side B&B information

Number of reviews
2,983
Accommodation
0 B&B
Lowest Price
CA $194
Highest Price
CA $434

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