Photo by Monica Ferro

Find a Bed and Breakfast in Countryside from CA $59

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Browse Select Countryside B&B

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (508)
"Complimentary breakfast was far beyond "continental", it was handmade from scratch and incredible! That's what really stood out. Otherwise my stay was also great, everything the listing claimed to be."
The price is CA $68
CA $138 total
includes taxes & fees
Dec 29 - Dec 30
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very good, (11)
"UwU"
The price is CA $59
CA $119 total
includes taxes & fees
Jan 14 - Jan 15, 2025
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, (337)
"I chose Rays s it was conveniently located near my client. A B&B would never be my choice for a business trip but I feel lucky I found this place. Great accommodations. Felt like a mini vacation. I’m returning when I can. "
The price is CA $214
CA $241 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (440)
"The Sono Chicago was a dream! Staff & Owner were friendly, accommodating, and gave great advice for dining & entertainment. Our bed was comfortable, bathroom was luxurious, and the balcony was fun for morning coffee. There is a nice rooftop area with seating and fire tables where you can relax/socialize. Parking was convenient and FREE! I def recommend The Sono Chicago!"
The price is CA $217
CA $255 total
includes taxes & fees
Dec 29 - Dec 30
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (163)
"We absolutely loved our stay. The breakfast was amazing and the staff were great. We can’t wait to come back."
The price is CA $197
CA $223 total
includes taxes & fees
Jan 26 - Jan 27, 2025
The Publishing House B&B
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (107)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is CA $332
CA $368 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Harvey House Bed & Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (238)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is CA $262
CA $308 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Wicker Park Inn
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"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 CA $203
CA $320 total
includes taxes & fees
Jan 6 - Jan 7, 2025
House 5863 - Chicago Bed and Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (98)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is CA $295
CA $347 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Villa D' Citta
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 CA $206
CA $355 total
includes taxes & fees
Dec 27 - Dec 28
Wrigleyville Suites Room 1
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is CA $147
CA $277 total
includes taxes & fees
Dec 27 - Dec 28
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 CA $147
CA $277 total
includes taxes & fees
Dec 27 - Dec 28
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 CA $207
CA $357 total
includes taxes & fees
Dec 27 - Dec 28
Villa Dubois Guest House Room 2
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is CA $120
CA $245 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Dubois Guest House Room 101
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, (134)
"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is CA $176
CA $315 total
includes taxes & fees
Dec 27 - Dec 28
Dubois Guest House Room 201
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is CA $176
CA $315 total
includes taxes & fees
Dec 27 - Dec 28
Dubois Guest House Room 202
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)
"The property was clean and attractive. It’s located in downtown Homewood with an easy walking distance of restaurants and shopping. The door takes a little bit of time to figure out. You need to wait time before you can hear it lock. Some of the door knobs were coming loose. A few of the ceiling fixtures were coming loose as well. It was a safe, clean, convenient, affordable option. I appreciated that the host answered my questions right away. Guest should know that there is parking available in...
Rustic cottage-style condo within walking distance to downtown Homewood
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is CA $176
CA $315 total
includes taxes & fees
Dec 27 - Dec 28
Villa Dubois Guest House Room 4
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is CA $211
CA $361 total
includes taxes & fees
Dec 27 - Dec 28
Dubois Guest House Room 203
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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Other property types in Countryside

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (629)
"The view was excellent "
The price is CA $157
CA $227 total
includes taxes & fees
Dec 29 - Dec 30
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (343)
"Great stay "
Kasa Magnificent Mile Chicago
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"Outstanding accommodations! Will choose this property again for my travels."
The price is CA $178
CA $209 total
includes taxes & fees
Jan 15 - Jan 16, 2025
Sonder South Wabash
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.

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 Soldier 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: 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 Publishing House B&B: 11 rooms. 14.1 mi (22.7 km) from the heart of downtown. Enjoy the free full breakfast and winery. The Sono Chicago: 7 rooms. Located 15.7 mi (25.3 km) from the core of Countryside. Enjoy the rooftop terrace and fireplace in the lobby.
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 Soldier 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.