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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for South Side bed & breakfast

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

1. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
9.8 out of 10, Exceptional, (573 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 Rp2.224.947
Rp2.612.052 total
includes taxes & fees
24 Nov - 25 Nov
The Sono Chicago
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

2. 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 narrow stone pathway leading to a house with a green porch and a large tree overhanging the path.

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 Rp954.368
Rp1.843.822 total
includes taxes & fees
7 Dec - 8 Dec
The Villa Toscana
A patio with a grill, outdoor seating, and potted plants.

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 Rp3.729.774
Rp4.210.575 total
includes taxes & fees
8 Nov - 9 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 Rp3.722.180
Rp4.369.515 total
includes taxes & fees
2 Dec - 3 Dec
Villa D' Citta
A brick building with a round metal table and chairs, a blue door, and a small garden area with plants and a bench.

6. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (286 reviews)
"Loved the location"
United States
Mary
The price is Rp4.185.260
Rp4.913.060 total
includes taxes & fees
23 Nov - 24 Nov
Wicker Park Inn
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

7. 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
16 Nov - 17 Nov
House 5863 - Chicago Bed and Breakfast
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 Rp4.667.326
Rp5.179.770 total
includes taxes & fees
9 Nov - 10 Nov
Harvey House Bed & Breakfast
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

9. 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 Rp5.231.123
Rp5.905.414 total
includes taxes & fees
19 Nov - 20 Nov
The Publishing House B&B
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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Learn more about South Side

Discover the metropolitan area of South Side—museums, skyscrapers and top sights like Lake Michigan.

See all hotels in South Side
A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Top reviews in South Side

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.
The Sono Chicago

The Sono Chicago

The Sono Chicago
Near North Side

10/10 Excellent

What an amazing stay this was...super friendly staff who were so happy to help with any requests. The Sono is in Old Town with lots of great places to shop and eat nearby. Can't recommend it highly enough!
United Kingdom
Roger
Reviewed June 4, 2025
The Sono Chicago