Photo by Monica Ferro

Search B&B in Countryside

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 33 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 AED 426
AED 647 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 AED 447
AED 653 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 AED 698
AED 788 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 AED 767
AED 900 total
includes taxes & fees
4 Jun - 5 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 AED 885
AED 999 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 AED 1,094
AED 1,284 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 AED 1,094
AED 1,284 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 AED 962
AED 1,068 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 AED 494
AED 871 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 AED 590
AED 907 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 AED 620
AED 1,058 total
includes taxes & fees
3 Jun - 4 Jun
Dubois Guest House Room 202
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 322
AED 652 total
includes taxes & fees
29 May - 30 May
Dubois Guest House Room 101
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 496
AED 885 total
includes taxes & fees
4 Jun - 5 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 AED 496
AED 885 total
includes taxes & fees
16 Jun - 17 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 AED 620
AED 1,058 total
includes taxes & fees
3 Jun - 4 Jun
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is AED 372
AED 712 total
includes taxes & fees
29 May - 30 May
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 AED 520
AED 905 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 AED 494
AED 871 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.