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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Countryside bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (488 reviews)
"This is a hidden gem in Old Town. Much better than staying in a chain and much more comfortable. The room was perfect and we had several options to walk to dining. We will definitely be back to stay here. "
United States
Nicholas
The price is SAR 409
SAR 480 total
includes taxes & fees
19 Jan - 20 Jan
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, (195 reviews)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is SAR 648
SAR 732 total
includes taxes & fees
8 Feb - 9 Feb
The Publishing House B&B
Living area

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very Good, (101 reviews)
"It was nicee"
United States
Yesim
The price is SAR 118
SAR 270 total
includes taxes & fees
19 Jan - 20 Jan
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (628 reviews)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is SAR 91
SAR 257 total
includes taxes & fees
20 Jan - 21 Jan
The Villa Toscana
Courtyard

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497 reviews)
"Nice shared spaces"
United States
Erica
The price is SAR 370
SAR 659 total
includes taxes & fees
18 Jan - 19 Jan
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, (259 reviews)
"Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so."
United States
Jeffrey
Wicker Park Inn
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (113 reviews)
"Great place"
United States
Jeffrey
The price is SAR 772
SAR 906 total
includes taxes & fees
20 Jan - 21 Jan
Villa D' Citta
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (386 reviews)
"We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!"
United States
Kristin
The price is SAR 652
SAR 736 total
includes taxes & fees
15 Feb - 16 Feb
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, (122 reviews)
"Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park "
United States
Elizabeth
The price is SAR 866
SAR 961 total
includes taxes & fees
21 Jan - 22 Jan
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

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent
"El lugar es espectacular "
Laura 1-night trip
Posted 19 hours ago
Club Quarters Hotel Wacker at Michigan, Chicago

Frequently asked questions

Searching for B&Bs in Countryside?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're traveling solo and hoping to get some tips from locals, B&Bs can be a great choice for many travelers. If you're interested in discovering some top attractions, Michigan Avenue and Wrigley Field are worth a stop.
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 picturesque garden or a beautiful breakfast room, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Countryside?
Here are some well-liked B&Bs in the area: Dorothy's: 7 rooms. 17.1 mi (27.6 km) from the heart of Countryside.The Villa Toscana: 9 rooms. 17.1 mi (27.6 km) from the downtown core. The Sono Chicago: 7 rooms. 15.7 mi (25.3 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. The Publishing House B&B: 11 rooms. Located 14.1 mi (22.7 km) from the core of Countryside. Enjoy the free full breakfast and winery.
What's the best time of year to book my B&B in Countryside?
When you're planning your getaway to Countryside, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Countryside is 49 inches.
What is there to do in Countryside?
Travelers 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?
Mapping out your trip in and around Countryside is easy with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 7.3 mi (11.8 km) from the city center. You can also search for flights into Chicago O'Hare Intl. 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.