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Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for West Side bed & breakfast

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
$228 nightly
The price is $258
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Publishing House B&B
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
Private kitchen
The Sono Chicago

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (487)
"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 21 - Dec 22
Total with taxes and fees
The Sono Chicago
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
$75 nightly
The price is $82
Jan 18 - Jan 19, 2026
Total with taxes and fees
Dorothy's
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497)
"Nice shared spaces"
United States
Erica
$141 nightly
The price is $166
Jan 4 - Jan 5, 2026
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
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
$76 nightly
The price is $82
Dec 22 - Dec 23
Total with taxes and fees
The Villa Toscana
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 29 - Dec 30
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, (383)
"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
$152 nightly
The price is $172
Dec 21 - Dec 22
Total with taxes and fees
Ray's Bucktown B&B
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
Jan 7 - Jan 8, 2026
Total with taxes and fees
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 West Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"The room was clean, but basic. The restaurant and food was great. The staff were very helpful and most were friendly. The location was excellent, a safe neighborhood with many restaurants and nice stores including Whole Foods in short walking distance. I'd stay here again. Try eating at Meli and Nancy's Pizza."
Robin 5-night trip
Posted 1 day ago
Crowne Plaza Chicago West Loop by IHG

Find out more about West Side

West Side B&B information

Number of reviews
2,548
Accommodation
2 B&B
Lowest Price
$82
Highest Price
$258

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