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
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

Our top choices for South 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, (192 reviews)
"Fun unique apartment above a wonderful pizza place! Great location and the stay was just great!"
United States
Mick
The price is €73
includes taxes & fees
16 Nov - 17 Nov
Dorothy's
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

2. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (683 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is €99
includes taxes & fees
16 Nov - 17 Nov
The Villa Toscana
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

3. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (568 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 €138
includes taxes & fees
2 Nov - 3 Nov
The Sono Chicago
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, (421 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is €191
includes taxes & fees
25 Oct - 26 Oct
Ray's Bucktown B&B
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

5. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (221 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
The price is €244
includes taxes & fees
1 Nov - 2 Nov
The Publishing House B&B
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

6. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (523 reviews)
"Honestly great, clean, and did not hear neighbors. Would stay again!"
United States
Malena
The price is €179
includes taxes & fees
2 Nov - 3 Nov
House 5863 - Chicago Bed and Breakfast
A grand foyer with a wooden staircase, a chandelier, and a large window.

7. 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 €263
includes taxes & fees
2 Nov - 3 Nov
Villa D' Citta
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, (286 reviews)
"Loved the location"
United States
Mary
The price is €277
includes taxes & fees
10 Nov - 11 Nov
Wicker Park Inn
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

9. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (137 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is €256
includes taxes & fees
5 Nov - 6 Nov
Harvey House Bed & Breakfast
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is €352
includes taxes & fees
27 Oct - 28 Oct
Pristine Apartment with Free Street Parking
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

Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Very convenient and clean"
Trami 3-night trip
Posted 12 hours ago
Jaslin Hotel

Find out more about South Side

South Side B&B information

Number of reviews
2,477
Accommodation
0 B&B
Lowest Price
€73
Highest Price
€352

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