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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured B&B in Far Southwest Side

Dorothy's
Relax in this stylish living area with a large sofa, glass coffee table, and patterned rug.

Dorothy's

3.0 star property
8.4 out of 10, Very good, (57)
"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 S$193
includes taxes & fees
3 Aug - 4 Aug
Dorothy's
The Villa Toscana
Stroll through this charming neighborhood to a traditional two-story house with a cozy front porch and balcony.

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (587)
"Was a great stay!"
The price is S$215
includes taxes & fees
4 Aug - 5 Aug
The Villa Toscana
House 5863 - Chicago Bed and Breakfast
Stunning corner building with a brick facade and large windows, surrounded by lush greenery.

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (475)
"I loved it was so close to busy Chicago but in the quiet subarbs where it was nice and quiet and felt very safe.The rooms were excellent and well equipped and the kitchen was full of snacks to eat when you wanted and a great selection of drinks. If I ever came to Chicago I would stay here again also the hosts were fantastic "
The price is S$278
includes taxes & fees
3 Aug - 4 Aug
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Experience the charm of this historic building, featuring a welcoming entrance, lush garden, and large windows offering views of the surrounding area.

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (368)
"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 S$298
includes taxes & fees
4 Aug - 5 Aug
Ray's Bucktown B&B
Wicker Park Inn
Welcome to The Wicker Park Inn, a charming urban B&B located at 1329 N. Wicker Park.

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (249)
"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
The Sono Chicago
Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
The price is S$303
includes taxes & fees
4 Aug - 5 Aug
The Sono Chicago
The Publishing House B&B
Staircase leads to an upper level with potted plants and decorative shelves.

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 S$298
includes taxes & fees
20 Aug - 21 Aug
The Publishing House B&B
Harvey House Bed & Breakfast
Enter a classic space with a traditional feel, featuring a dresser, lamp, and ornate rug.

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (113)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is S$384
includes taxes & fees
6 Aug - 7 Aug
Harvey House Bed & Breakfast
Villa D' Citta
Step into a grand lobby with a classic staircase, elegant seating area, and beautiful views.

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (104)
"Would stay again anytime!!"
The price is S$448
includes taxes & fees
13 Aug - 14 Aug
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 Far Southwest Side Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Great spot. Definitely an older property but clean, nice breakfast and lovely staff "
Libby 2-night trip
Posted 9 hours ago
The Whitehall Hotel, BW Premier Collection