Chicago South Side

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Our top choices for South Side bed & breakfast

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (526 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is £136
includes taxes & fees
6 Jul - 7 Jul
The Sono Chicago

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (208 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is £253
includes taxes & fees
19 Jul - 20 Jul
The Publishing House B&B

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (140 reviews)
"lots of clean rooms and clean bathrooms with products you can use. keep in mind however that not every room has its own private bathroom "
United States
Jia
The price is £90
includes taxes & fees
13 Jul - 14 Jul
Dorothy's

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (651 reviews)
"Small, but very convenient! Excellent location!"
Canada
Jeremy
The price is £125
includes taxes & fees
13 Jul - 14 Jul
The Villa Toscana

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (507 reviews)
"The place is well run. The communal areas are clean and have what you need. The neighborhood is nice, everyone i took was gorgeous! And the perfect distance from the city."
United States
Joanna
The price is £163
includes taxes & fees
8 Jul - 9 Jul
House 5863 - Chicago Bed and Breakfast

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (402 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is £176
includes taxes & fees
30 Jun - 1 Jul
Ray's Bucktown B&B

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (128 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
The price is £227
includes taxes & fees
6 Jul - 7 Jul
Harvey House Bed & Breakfast

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (268 reviews)
"Very nice place and great location with a lot of restaurants and shops."
United States
Regina
The price is £203
includes taxes & fees
7 Jul - 8 Jul
Wicker Park Inn

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (121 reviews)
"A fantastic stay yet again. I have stayed here the last few years while attending a conference. All the staff were great and amazing selection of food for breakfast and for late night snacks. I will be back again next year"
United Kingdom
Robert
The price is £254
includes taxes & fees
1 Jul - 2 Jul
Villa D' Citta

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is £354
includes taxes & fees
30 Jun - 1 Jul
Pristine Apartment with Free Street Parking

Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
The price is £1,123
includes taxes & fees
13 Jul - 14 Jul
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

Find out more about South Side

South Side B&B information

Number of reviews
2,951
Accommodation
0 B&B
Lowest Price
£90
Highest Price
£1,123

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in South Side?
Prices for B&Bs in South Side often vary, but you can find a great deal from £90 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 B&B in South Side?
The most popular time to book a B&B in South Side is during the vibrant summer months, particularly July. This season brings a flurry of activity, as visitors flock to the area to enjoy outdoor festivals, cultural events, and the bustling local art scene. The warm weather, with temperatures typically in the mid to high 20s Celsius, creates an inclusive setting for exploring the neighbourhood's parks, galleries, and trendy eateries.

In South Side, the peak tourist season runs from June through August, when the community comes alive with various happenings. Whether you're strolling along the riverside paths or indulging in the local culinary delights, there's plenty to keep you engaged. July, in particular, is a highlight, offering the superb balance of sun-soaked days and lively nightlife, making it an ideal time for social travellers looking to connect with others.

For those seeking a more budget-friendly option, visiting in December can be a wonderful choice. While the weather is cooler, often hovering around 5 to 10 degrees Celsius, this month allows you to experience South Side's festive charm without the crowds. The holiday decorations and seasonal events create a cosy atmosphere, superb for enjoying leisurely walks and intimate dining experiences.
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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