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Our top choices for South Side bed & breakfast

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (182 reviews)
"The room was extremely clean and nicely set up! The ac was tooo cold but other than that, Loved my 3 day-stay and would stay again!"
United States
Felicia
The price is £101
includes taxes & fees
30 Sept - 1 Oct
Dorothy's

2. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (675 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 £101
includes taxes & fees
21 Sept - 22 Sept
The Villa Toscana

3. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (555 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 £205
includes taxes & fees
30 Sept - 1 Oct
The Sono Chicago

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (415 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is £151
includes taxes & fees
27 Sept - 28 Sept
Ray's Bucktown B&B

5. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (517 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 £156
includes taxes & fees
30 Sept - 1 Oct
House 5863 - Chicago Bed and Breakfast

6. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (215 reviews)
"Gorgeous building inside and out. Beautiful clean rooms. Amazing public spaces. Breakfast was by far one of the best meals of the whole trip."
United States
Mollie
The price is £252
includes taxes & fees
14 Oct - 15 Oct
The Publishing House B&B

7. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (125 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 £221
includes taxes & fees
5 Oct - 6 Oct
Villa D' Citta

8. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (135 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is £243
includes taxes & fees
21 Sept - 22 Sept
Harvey House Bed & Breakfast

9. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (282 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is £278
includes taxes & fees
28 Sept - 29 Sept
Wicker Park Inn

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is £329
includes taxes & fees
20 Oct - 21 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

Find out more about South Side

South Side B&B information

Number of reviews
2,459
Accommodation
0 B&B
Lowest Price
£101
Highest Price
£329

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 £101 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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