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
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

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, (565 reviews)
"It was a very comfortable hotel. We loved the free street parking, easy access to public transportation, coffee, breakfast, bottled water, bubbly water and snacks. I will stay here again!"
United States
Christie
The price is AU$299
includes taxes & fees
29 Oct - 30 Oct
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, (191 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is AU$121
includes taxes & fees
2 Nov - 3 Nov
Dorothy's
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

3. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (219 reviews)
"Beautiful space"
United States
Mary
The price is AU$368
includes taxes & fees
25 Oct - 26 Oct
The Publishing House B&B
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

4. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (682 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is AU$171
includes taxes & fees
2 Nov - 3 Nov
The Villa Toscana
A bathroom with a glass-tiled wall, a sink, and a shower area.

5. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (420 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is AU$299
includes taxes & fees
13 Oct - 14 Oct
Ray's Bucktown B&B
A grand foyer with a wooden staircase, a chandelier, and a large window.

6. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (127 reviews)
"Very elegant !"
United States
Hernando
The price is AU$423
includes taxes & fees
26 Oct - 27 Oct
Villa D' Citta
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

7. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (285 reviews)
"Loved the location"
United States
Mary
The price is AU$444
includes taxes & fees
1 Nov - 2 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, (136 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is AU$410
includes taxes & fees
5 Nov - 6 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, (521 reviews)
"good"
United States
jiantao
The price is AU$300
includes taxes & fees
26 Oct - 27 Oct
House 5863 - Chicago Bed and 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 AU$550
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 nice hotel! We had a great view of the Sears Tower from our room! A+ stay!"
Barry 2-night trip
Posted 3 hours ago
Jaslin Hotel

Find out more about South Side

South Side B&B information

Number of reviews
2,791
Accommodation
0 B&B
Lowest Price
AU$121
Highest Price
AU$550

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