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Check prices for these dates

Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov

Featured B&B in Southwest Side and around

Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very good, (76)
"Clean room beautiful.yards convenient"
The price is €96
includes taxes & fees
29 Sept - 30 Sept
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (607)
"Just a wonderful tranquil oasis in such a large city and busy section of town."
The price is €118
includes taxes & fees
7 Oct - 8 Oct
The Villa Toscana
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (476)
"Loved the shared kitchen access! "
The price is €209
includes taxes & fees
29 Sept - 30 Sept
The Sono Chicago
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (375)
"Absolutely one of the best stays I’ve ever had. "
The price is €155
includes taxes & fees
25 Sept - 26 Sept
Ray's Bucktown B&B
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (185)
"Wonderful staff, beautiful hotel and great breakfast!"
The price is €213
includes taxes & fees
6 Oct - 7 Oct
The Publishing House B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (481)
"Everything was taken care of! A wonderful stay. "
The price is €161
includes taxes & fees
24 Sept - 25 Sept
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (252)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (107)
"Would stay again anytime!!"
The price is €262
includes taxes & fees
7 Oct - 8 Oct
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is €246
includes taxes & fees
24 Sept - 25 Sept
Harvey House Bed & Breakfast
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (147)
"Great location. Location was clean and everything was good!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is €212
includes taxes & fees
24 Sept - 25 Sept
Villa Dubois Guest Room 6
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is €251
includes taxes & fees
24 Sept - 25 Sept
Dubois Guest House Room 101
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is €207
includes taxes & fees
25 Sept - 26 Sept
Villa Dubois Guest House Room 5
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is €251
includes taxes & fees
24 Sept - 25 Sept
Dubois Guest House Room 201
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is €251
includes taxes & fees
24 Sept - 25 Sept
Villa Dubois Guest House Room 2
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is €251
includes taxes & fees
24 Sept - 25 Sept
Villa Dubois Guest House Room 4
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
The price is €251
includes taxes & fees
24 Sept - 25 Sept
Dubois Guest House Room 202
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

Wrigleyville Suites Room 5
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is €292
includes taxes & fees
24 Sept - 25 Sept
Villa Dubois Guest House Room 1
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 Southwest Side Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great location, felt safe, even though I traveled with spouse. A single female traveler would feel safe staying at this location. Nice clean hotel, pretty decor in the common area of lobby, staff are polite and friendly, willing to help. The connection restaurant was friendly, limited menu bit food is good. Highly recommended "
Tangee 5-night trip
Posted 16 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Southwest Side

Find out more about Southwest Side

Southwest Side B&B information

Number of reviews
2,552
Accommodation
19 B&B
Lowest Price
€96
Highest Price
€292

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