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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured B&B in Countryside

Private kitchen
The Sono Chicago

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (483)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
The price is AU$234
includes taxes & fees
8 Dec - 9 Dec
The Sono Chicago
Lobby sitting area
Villa D' Citta

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (111)
"Great place"
United States
Jeffrey
The price is AU$366
includes taxes & fees
16 Dec - 17 Dec
Villa D' Citta
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12

Lakeview
The price is AU$1,565
includes taxes & fees
17 Dec - 18 Dec
Five bedroom - 3 bath - Sleeps 12
Free WiFi, bed sheets
Dorothy's

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very good, (97)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
The price is AU$113
includes taxes & fees
4 Jan - 5 Jan 2026
Dorothy's
Exterior
The Villa Toscana

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (624)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is AU$121
includes taxes & fees
4 Jan - 5 Jan 2026
The Villa Toscana
Staircase
The Publishing House B&B

The Publishing House B&B

3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (188)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is AU$331
includes taxes & fees
18 Dec - 19 Dec
The Publishing House B&B
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (492)
"Easy check-in, c. Easy parking. "
United States
Jordan
The price is AU$286
includes taxes & fees
10 Dec - 11 Dec
House 5863 - Chicago Bed and Breakfast
Property entrance
Wicker Park Inn

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
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, (382)
"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
The price is AU$270
includes taxes & fees
7 Dec - 8 Dec
Ray's Bucktown B&B
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (120)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
United States
Bethany
The price is AU$388
includes taxes & fees
9 Dec - 10 Dec
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 Countryside Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Location of the Hotel is very nice and the hotel is very clean."
Khaing 1-night trip
Posted 1 day ago
River Hotel

Find out more about Countryside

Countryside B&B information

Number of reviews
2,528
Accommodation
13 B&B
Lowest Price
AU$113
Highest Price
AU$1,565

Frequently asked questions

Searching for B&Bs in Countryside?
Whether you're passing through town and are looking for accommodation that's small and charming, or you're travelling solo and hoping to get some tips from locals, B&Bs can be a great choice for many types of holidaymakers. If you're interested in discovering some top attractions, Michigan Avenue and Wrigley Field are worth a visit.
How do you know if a B&B is the best choice for your stay?
Every B&B has its own unique feel — whether it's a cosy reading space or a sunlit breakfast nook, the tiny details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Countryside?
Here are some well-liked B&Bs in the area: The Sono Chicago: 7 rooms. 15.7 mi (25.3 km) from the heart of Countryside. Enjoy the rooftop terrace and fireplace in reception. Dorothy's: 7 rooms. 17.1 mi (27.6 km) from the city centre. The Villa Toscana: 9 rooms. Situated 17.1 mi (27.6 km) from the heart of Countryside. Ray's Bucktown B&B: 11 rooms. 14.7 mi (23.7 km) from the city centre. Enjoy the free cooked breakfast and rooftop terrace.
When should I book my B&B in Countryside?
When you're planning your escape to Countryside, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Countryside is 1236 mm.
What is there to do in Countryside?
Travellers enjoy Countryside for its restaurants and shopping. Michigan Avenue and Wrigley Field are also some sites to visit if you want to see more of the area.
How can I get to and around Countryside?
You can map out your trip in and around Countryside ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 7.3 mi (11.8 km) away. You can also search for flights into Chicago O'Hare International Airport (ORD), which is 14.6 mi (23.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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