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
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is P3,561
P6,378 total
includes taxes & fees
Nov 3 - Nov 4
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, (682 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is P4,618
P7,933 total
includes taxes & fees
Nov 2 - Nov 3
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, (566 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 P10,418
P12,229 total
includes taxes & fees
Oct 26 - Oct 27
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, (420 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is P12,614
P14,240 total
includes taxes & fees
Oct 25 - Oct 26
Ray's Bucktown B&B
A grand foyer with a wooden staircase, a chandelier, and a large window.

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 P15,816
P18,567 total
includes taxes & fees
Oct 26 - Oct 27
Villa D' Citta
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, (521 reviews)
"good"
United States
jiantao
The price is P7,461
P12,601 total
includes taxes & fees
Oct 19 - Oct 20
House 5863 - Chicago Bed and Breakfast
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 P16,604
P19,492 total
includes taxes & fees
Nov 1 - Nov 2
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 P16,210
P17,989 total
includes taxes & fees
Nov 5 - Nov 6
Harvey House Bed & 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 South Side Hotel Reviews

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Very clean room with working microwave ave fridge. Perfect for a stay close to the city!"
Nicole 1-night trip
Posted 1 hour ago
Chicago Lake Shore Hotel

Find out more about South Side

South Side B&B information

Number of reviews
2,229
Accommodation
0 B&B
Lowest Price
P6,378
Highest Price
P19,492