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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Southwest Side B&B

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very good, (63)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
The price is £83
includes taxes & fees
1 Sept - 2 Sept
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (590)
"Was a great stay!"
The price is £100
includes taxes & fees
17 Aug - 18 Aug
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (369)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is £158
includes taxes & fees
18 Aug - 19 Aug
Ray's Bucktown 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, (479)
"Everything was taken care of! A wonderful stay. "
The price is £156
includes taxes & fees
24 Aug - 25 Aug
House 5863 - Chicago Bed and Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is £166
includes taxes & fees
2 Sept - 3 Sept
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (251)
"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
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (115)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is £221
includes taxes & fees
21 Aug - 22 Aug
Harvey House Bed & Breakfast
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (466)
"Loved the shared kitchen access! "
The price is £131
includes taxes & fees
17 Aug - 18 Aug
The Sono Chicago
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, (143)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
The price is £228
includes taxes & fees
18 Aug - 19 Aug
Villa D' Citta
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is £136
includes taxes & fees
17 Aug - 18 Aug
Villa Dubois Guest Room 6
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is £136
includes taxes & fees
17 Aug - 18 Aug
Dubois Guest House Room 101
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 £136
includes taxes & fees
17 Aug - 18 Aug
Dubois Guest House Room 201
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is £136
includes taxes & fees
17 Aug - 18 Aug
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is £136
includes taxes & fees
17 Aug - 18 Aug
Villa Dubois Guest House Room 2
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
The price is £220
includes taxes & fees
19 Aug - 20 Aug
Dubois Guest House Room 202
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is £254
includes taxes & fees
24 Aug - 25 Aug
Villa Dubois Guest House Room 1
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is £1,262
includes taxes & fees
27 Aug - 28 Aug
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 Southwest Side Hotel Reviews

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Everyone was extremely nice and helpful! I would definitely stay again when I come into Chicago!"
LaShawn 4-night trip
Posted 3 hours ago
Fairmont Chicago at Millennium Park