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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Southwest Side bed & breakfast

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (197 reviews)
"I enjoyed my stay"
United States
Kellen
The price is Rp519.154
Rp1.242.550 total
includes taxes & fees
7 Dec - 8 Dec
Dorothy's
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
9.8 out of 10, Exceptional, (575 reviews)
"I like that it had a balcony food choice wasn’t my type of style end up ordering food off of site but definitely had all the amenities for you to be ready for the next day. Will be staying again little bit pricey for a short weekend stay but I will definitely be coming back. Very great part of the town hope to own my own own home in this place one day."
United States
Tavarion
The price is Rp2.387.748
Rp2.802.891 total
includes taxes & fees
23 Nov - 24 Nov
The Sono Chicago
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

3. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.2 out of 10, Very good, (690 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is Rp842.405
Rp1.712.486 total
includes taxes & fees
10 Nov - 11 Nov
The Villa Toscana
A bathroom with a glass-tiled wall, a sink, and a shower area.

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (423 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is Rp3.340.496
Rp3.771.014 total
includes taxes & fees
10 Nov - 11 Nov
Ray's Bucktown B&B
A courtyard with brick arches, outdoor seating, and potted plants.

5. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (129 reviews)
"Very elegant !"
United States
Hernando
The price is Rp3.723.621
Rp4.371.207 total
includes taxes & fees
2 Dec - 3 Dec
Villa D' Citta
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

6. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (222 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
The price is Rp4.874.986
Rp5.503.371 total
includes taxes & fees
10 Dec - 11 Dec
The Publishing House B&B
A brick building with a round metal table and chairs, a blue door, and a small garden area with plants and a bench.

7. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (287 reviews)
"Loved the location"
United States
Mary
The price is Rp3.789.646
Rp4.448.809 total
includes taxes & fees
16 Nov - 17 Nov
Wicker Park Inn
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

8. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (138 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is Rp4.669.133
Rp5.181.775 total
includes taxes & fees
10 Nov - 11 Nov
Harvey House Bed & Breakfast
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

9. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (525 reviews)
"Honestly great, clean, and did not hear neighbors. Would stay again!"
United States
Malena
The price is Rp2.062.146
Rp3.521.567 total
includes taxes & fees
10 Nov - 11 Nov
House 5863 - Chicago Bed and Breakfast
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

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"This hotel has a great location. It is walking distance to everything you want to do in Chicago. Check in was quick and the staff were friendly and efficient. The rooms are clean with more than enough room for a pleasant weekend stay. They offer valet parking but we parked across the street to m self park. Great value for the stay."
Tricia 3-night trip
Posted less than an hour ago
Hotel Saint Clair- Magnificent Mile

Find out more about Southwest Side

Southwest Side B&B information

Number of reviews
2,403
Accommodation
9 B&B
Lowest Price
Rp1.242.550
Highest Price
Rp5.503.371