A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

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
10.0 out of 10, Exceptional, (541 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is NT$4,779
NT$5,610 total
includes taxes & fees
Aug 24 - Aug 25
The Sono Chicago
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

2. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (211 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is NT$7,412
NT$8,367 total
includes taxes & fees
Aug 31 - Sep 1
The Publishing House B&B
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

3. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (172 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is NT$1,910
NT$6,889 total
includes taxes & fees
Aug 24 - Aug 25
Dorothy's
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, (413 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is NT$5,539
NT$6,254 total
includes taxes & fees
Aug 23 - Aug 24
Ray's Bucktown B&B
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

5. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very Good, (666 reviews)
"Was a nice house the room we stayed in was cozy bed was really comfortable and in walking distance to wrigley field would definitely stay here again"
United States
John
The price is NT$2,649
NT$4,384 total
includes taxes & fees
Aug 24 - Aug 25
The Villa Toscana
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

6. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (132 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is NT$8,634
NT$9,582 total
includes taxes & fees
Aug 25 - Aug 26
Harvey House Bed & Breakfast
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, (515 reviews)
"I love the location of this B&B. Right across from a beautiful park, walkable to some fabulous restaurants and shops - and the red line is so close! My room was clean, quiet, cutely decorated. The kitchen was well-stocked with breakfast options. My one recommendation would be - I wish the coffee was higher quality! The host was prompt, friendly, and responsive to my needs. I'll be back for sure!"
United States
Kimberly
The price is NT$4,014
NT$6,678 total
includes taxes & fees
Aug 24 - Aug 25
House 5863 - Chicago Bed and Breakfast
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (280 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is NT$10,110
NT$11,867 total
includes taxes & fees
Sep 14 - Sep 15
Wicker Park Inn
A grand foyer with a wooden staircase, a chandelier, and a large window.

9. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (122 reviews)
"Wonderful! Will stay here again."
United States
Elsa
The price is NT$8,390
NT$9,849 total
includes taxes & fees
Aug 23 - Aug 24
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 South Side Hotel Reviews

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"The hotel was excellent! It was in a perfect location. You could walk to restaurants and shops. The staff was friendly, helpful and knowledgeable."
Ronda 2-night trip
Posted 19 hours ago
Hyatt Place Chicago-South/University Medical Center

Find out more about South Side

South Side B&B information

Number of reviews
2,098
Accommodation
0 B&B
Lowest Price
NT$4,384
Highest Price
NT$11,867

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