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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured B&B in South Side and around

Private kitchen
The Sono Chicago

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (484)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
The price is €137
includes taxes & fees
9 Dec - 10 Dec
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, (188)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is €287
includes taxes & fees
21 Dec - 22 Dec
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very good, (97)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
The price is €69
includes taxes & fees
4 Jan - 5 Jan 2026
Dorothy's
Exterior
The Villa Toscana

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (625)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is €70
includes taxes & fees
10 Dec - 11 Dec
The Villa Toscana
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (493)
"Easy check-in, c. Easy parking. "
United States
Jordan
The price is €155
includes taxes & fees
10 Dec - 11 Dec
House 5863 - Chicago Bed and Breakfast
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (120)
"Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park "
United States
Elizabeth
The price is €220
includes taxes & fees
9 Dec - 10 Dec
Harvey House Bed & Breakfast
Lobby sitting area
Villa D' Citta

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (112)
"Great place"
United States
Jeffrey
The price is €208
includes taxes & fees
16 Dec - 17 Dec
Villa D' Citta
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 star property
Bucktown
9.8 out of 10, Exceptional, (382)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is €153
includes taxes & fees
9 Dec - 10 Dec
Ray's Bucktown B&B
Property entrance
Wicker Park Inn

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12

Lakeview
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.
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Top South Side Hotel Reviews

Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"Staff is great, clean rooms "
May 2-night trip
Posted 2 days ago
Carlton Inn Midway

Find out more about South Side

South Side B&B information

Number of reviews
2,534
Accommodation
9 B&B
Lowest Price
€69
Highest Price
€287

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