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
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

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, (545 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 P9,339
P10,964 total
includes taxes & fees
Sep 2 - Sep 3
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, (212 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is P15,370
P17,351 total
includes taxes & fees
Aug 30 - Aug 31
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, (173 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is P3,657
P13,316 total
includes taxes & fees
Aug 30 - Aug 31
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 P11,356
P12,820 total
includes taxes & fees
Aug 31 - Sep 1
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, (669 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 P5,144
P8,512 total
includes taxes & fees
Aug 30 - Aug 31
The Villa Toscana
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, (516 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 P7,794
P12,965 total
includes taxes & fees
Sep 13 - Sep 14
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, (123 reviews)
"What a pleasant stay, staff was welcoming and wanting to make sure our needs were met with our expectations. Meals were abundant and homemade. Rooms w/bath were clean with abundant towels. We will stay again."
United States
Jeffrey
The price is P17,712
P20,792 total
includes taxes & fees
Aug 30 - Aug 31
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, (281 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is P17,156
P20,139 total
includes taxes & fees
Aug 31 - Sep 1
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, (132 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is P16,762
P18,603 total
includes taxes & fees
Aug 31 - Sep 1
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

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"We arrived super late and the front desk was exceptional! Amazing stay! 10/10 will return to this hotel on our next visit"
Joyce 2-night trip
Posted 21 hours ago
Holiday Inn Chicago – Midway Airport S by IHG

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