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Check prices for these dates

Next weekend
Jul 25 - Jul 27
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Aug 1 - Aug 3
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Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Featured B&B in 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
8.6 out of 10, Excellent, (52)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
The price is P5,662
P8,649 total
includes taxes & fees
Jul 20 - Jul 21
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, (585)
"Was a great stay!"
The price is P6,597
P10,035 total
includes taxes & fees
Jul 24 - Jul 25
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, (474)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is P7,827
P12,425 total
includes taxes & fees
Jul 20 - Jul 21
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, (367)
"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 P11,488
P12,969 total
includes taxes & fees
Jul 22 - Jul 23
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, (464)
"Excellent location. Beautiful property, extremely clean."
The price is P12,971
P15,227 total
includes taxes & fees
Jul 23 - Jul 24
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 P14,577
P16,456 total
includes taxes & fees
Aug 7 - Aug 8
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, (112)
"Enjoyed my short stay. Wish I could have spent more time here! Quiet, peaceful, safe, and comfortable. I travel frequently for work and this is by far, one of the best experiences I have had. Thank you Beth!"
The price is P15,004
P17,177 total
includes taxes & fees
Jul 24 - Jul 25
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, (103)
"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"
The price is P17,035
P19,998 total
includes taxes & fees
Aug 11 - Aug 12
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 Southwest Side Hotel Reviews

Swissotel - Chicago

Swissotel - Chicago

10/10 Excellent
"This Is Legitimately The Best & Nicest Hotel I Have Ever Stayed At. Definitely Will Be Staying At Swissotel Each Time I Visit The Windy City!! "
Bradley 4-night trip
Posted 16 hours ago
Swissotel - Chicago