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Check prices for these dates

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

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
$131 nightly
The price is $154
Dec 18 - Dec 19
Total with taxes and fees
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
$188 nightly
The price is $213
Dec 18 - Dec 19
Total with taxes and fees
The Publishing House B&B
Exterior
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
$149 nightly
The price is $174
Jan 4 - Jan 5, 2026
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
Free WiFi, bed sheets
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
$69 nightly
The price is $75
Dec 18 - Dec 19
Total with taxes and fees
Dorothy's
Exterior
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
$75 nightly
The price is $81
Dec 17 - Dec 18
Total with taxes and fees
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
$206 nightly
The price is $242
Dec 16 - Dec 17
Total with taxes and fees
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
$186 nightly
The price is $218
Jan 5 - Jan 6, 2026
Total with taxes and fees
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
$231 nightly
The price is $256
Dec 15 - Dec 16
Total with taxes and fees
Harvey House Bed & Breakfast
Front of property
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
$147 nightly
The price is $166
Dec 16 - Dec 17
Total with taxes and fees
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"This place was very nice. The staff were great, the hotel was very clean, and I will definitely stay here again.”"
Tiana 3-night trip
Posted 4 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Far Southwest Side

Far Southwest Side B&B information

Number of reviews
2,541
Accommodation
11 B&B
Lowest Price
$75
Highest Price
$256

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