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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Far Southwest Side bed & breakfast

Private kitchen
The Sono Chicago

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (486)
"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 €132
includes taxes & fees
22 Dec - 23 Dec
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (189)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is €195
includes taxes & fees
18 Dec - 19 Dec
The Publishing House B&B
Courtyard
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.0 out of 10, Wonderful, (495)
"Cool and clean hotel. Erick was friendly and accommodating."
United States
Samantha
The price is €149
includes taxes & fees
5 Jan - 6 Jan 2026
House 5863 - Chicago Bed and Breakfast
Living area
Dorothy's

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 €61
includes taxes & fees
15 Dec - 16 Dec
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio
The Villa Toscana

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (627)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is €65
includes taxes & fees
17 Dec - 18 Dec
The Villa Toscana
Lobby sitting area
Villa D' Citta

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (113)
"Great place"
United States
Jeffrey
The price is €206
includes taxes & fees
16 Dec - 17 Dec
Villa D' Citta
Property entrance
Wicker Park Inn

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
Property entrance
Harvey House Bed & Breakfast

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 €218
includes taxes & fees
18 Dec - 19 Dec
Harvey House Bed & Breakfast
Spa
Ray's Bucktown B&B

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 €142
includes taxes & fees
16 Dec - 17 Dec
Ray's Bucktown B&B
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 Far Southwest Side Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Great place always. "
Robert 1-night trip
Posted 12 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Far Southwest Side

Far Southwest Side B&B information

Number of reviews
2,540
Accommodation
24 B&B
Lowest Price
€61
Highest Price
€218

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