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Nov 21 - Nov 23
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B&B in South Side

Private kitchen
The Sono Chicago

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (481)
"Great location and hospitality! "
United States
Teresa
$131 nightly
The price is $154
Nov 20 - Nov 21
Total with taxes and fees
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (187)
"This was my first time ever booking at a bed & breakfast and it was amazing!!! The staff were so helpful & great. The breakfast was very delicious. My room was perfect & clean. Everyone was so lovely. Can’t wait to go back!!!"
United States
Jazmine
$210 nightly
The price is $238
Nov 16 - Nov 17
Total with taxes and fees
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very Good, (92)
"Halsted is a nice neibourhood. We liked the secondhand shops."
United States
Lisa
$78 nightly
The price is $86
Nov 16 - Nov 17
Total with taxes and fees
Dorothy's
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (491)
"I loved it was so close to busy Chicago but in the quiet subarbs where it was nice and quiet and felt very safe.The rooms were excellent and well equipped and the kitchen was full of snacks to eat when you wanted and a great selection of drinks. If I ever came to Chicago I would stay here again also the hosts were fantastic "
United Kingdom
Mark
$156 nightly
The price is $183
Nov 16 - Nov 17
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
Exterior
The Villa Toscana

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (617)
"We "
United States
Brian
$82 nightly
The price is $90
Nov 17 - Nov 18
Total with taxes and fees
The Villa Toscana
Lobby sitting area
Villa D' Citta

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (110)
"Would stay again anytime!!"
United States
Dominic
$206 nightly
The price is $242
Dec 1 - Dec 2
Total with taxes and fees
Villa D' Citta
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (119)
"Beautiful home, welcoming host."
United States
scott
$231 nightly
The price is $256
Nov 17 - Nov 18
Total with taxes and fees
Harvey House Bed & Breakfast
Property entrance
Wicker Park Inn

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"My husband and I loved our stay. The room was beautiful, clean, and comfortable. Being able to stay in a neighborhood inn made our trip to Chicago memorable. We went to the Wicker Park Farmer's Market, ate at local restaurants, hung out at local bars, met cool people, and just enjoyed being part of the city. "
United States
Melissa
$209 nightly
The price is $245
Dec 7 - Dec 8
Total with taxes and fees
Wicker Park Inn
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 star property
Bucktown
9.8 out of 10, Exceptional, (381)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
$164 nightly
The price is $185
Nov 26 - Nov 27
Total with taxes and fees
Ray's Bucktown B&B
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12

Lakeview
$775 nightly
The price is $885
Dec 2 - Dec 3
Total with taxes and fees
Five bedroom - 3 bath - Sleeps 12
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 Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent
"The room, staff, and facilities were amazing, even breakfast was delicious!"
Luis 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Find out more about South Side

South Side B&B information

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Frequently asked questions

What is the nightly rate for a Bed & Breakfast in South Side?
Prices for B&Bs in South Side often vary, but you can find a great deal with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at South Side B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in South Side?
The best time to book a B&B in South Side is during the vibrant summer months, particularly July, when the area comes alive with energy and activity. This peak season, spanning from June to August, is superb for travelers who appreciate a bustling atmosphere and a wide range of outdoor activities. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, visitors can comfortably explore the beautiful parks, enjoy scenic walks along the river, and indulge in local festivals.

July stands out as the most popular month to visit South Side, offering an abundance of events, including markets and live performances that appeal to both families and solo travelers. The lively ambiance creates an inviting environment for those looking to connect with fellow adventurers while enjoying the beautiful summer weather.

For those seeking a more budget-friendly experience, consider planning your trip in October. This month allows you to experience the charm of South Side without the hustle of peak season. The fall foliage adds a picturesque quality to the landscape, making it an ideal time for leisurely strolls or relaxing afternoons at local cafes.
What is the difference between a South Side Bed and Breakfast and a hotel?
Every South Side B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at South Side B&Bs.

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