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Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 29 B&B in Countryside with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (557)
"Super easy to find parking, quick walk to cubs game and bars after. Safe neighborhood and the greatest pizza place right through the gate. It was awesome!"
The price is SAR 435
SAR 661 total
includes taxes & fees
5 Jun - 6 Jun
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (38)
"I initially came up to Chicago from Indiana and had found this place to stay for my duration. The area was lovely, arrangements were excellent and I loved the cottage feel to the Bed N’ Breakfast next door. If I’m ever in Chicago for another concert or to see more of the place, I’m coming back to Dorothy’s."
The price is SAR 459
SAR 670 total
includes taxes & fees
16 Jun - 17 Jun
Dorothy's
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (355)
"Breakfast was great, the staff was kind, and it was a pleasant surprise. "
The price is SAR 713
SAR 805 total
includes taxes & fees
3 Jun - 4 Jun
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (455)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is SAR 792
SAR 930 total
includes taxes & fees
2 Jun - 3 Jun
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (176)
"Incredible service, amazing breakfast and gorgeous rooms."
The price is SAR 903
SAR 1,020 total
includes taxes & fees
22 Jun - 23 Jun
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is SAR 1,117
SAR 1,311 total
includes taxes & fees
10 Jun - 11 Jun
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (100)
"What a wonderful and unique place where everything is so beautifully decorated with the owners personalized touch. The kitchen and amenities are exceptional and the best part was breakfast and visiting with Gina. Will be our only go-to now in Chicago."
The price is SAR 1,117
SAR 1,311 total
includes taxes & fees
2 Jun - 3 Jun
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
The price is SAR 983
SAR 1,091 total
includes taxes & fees
29 May - 30 May
Harvey House Bed & Breakfast
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (135)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
The price is SAR 505
SAR 889 total
includes taxes & fees
29 May - 30 May
Wrigleyville Suites Room 1
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (473)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is SAR 603
SAR 926 total
includes taxes & fees
3 Jun - 4 Jun
House 5863 - Chicago Bed and Breakfast
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is SAR 633
SAR 1,073 total
includes taxes & fees
5 Jun - 6 Jun
Dubois Guest House Room 202
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is SAR 633
SAR 1,081 total
includes taxes & fees
2 Jun - 3 Jun
Dubois Guest House Room 101
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is SAR 506
SAR 904 total
includes taxes & fees
5 Jun - 6 Jun
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is SAR 567
SAR 989 total
includes taxes & fees
18 Jun - 19 Jun
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is SAR 633
SAR 1,081 total
includes taxes & fees
5 Jun - 6 Jun
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is SAR 760
SAR 1,250 total
includes taxes & fees
2 Jun - 3 Jun
Dubois Guest House Room 203
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is SAR 531
SAR 925 total
includes taxes & fees
29 May - 30 May
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is SAR 505
SAR 889 total
includes taxes & fees
29 May - 30 May
Wrigleyville Suites Room 3
Rustic cottage-style condo within walking distance to downtown Homewood
Fridge, microwave, coffee/tea maker, toaster

Rustic cottage-style condo within walking distance to downtown Homewood

8.8 out of 10, Excellent, (10)
"Great location, close to Credit Union 1 amphlitheater and walking distance to a good breakfast spot. Quiet neighborhood and clean apartment. Perfect space for a girls’ getaway."
Rustic cottage-style condo within walking distance to downtown Homewood
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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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, Soldier Field and Michigan Avenue 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: The Villa Toscana: 9 rooms. 17.1 mi (27.6 km) from the heart of Countryside.Dorothy’s: 7 rooms. 17.1 mi (27.6 km) from the downtown core. Ray’s Bucktown B&B: 11 rooms. Situated 14.7 mi (23.7 km) from the heart of Countryside. Enjoy the free cooked breakfast and rooftop terrace. 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. Soldier Field and Michigan Avenue 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.