Photo by Monica Ferro

Find a Bed and Breakfast in Countryside from CA $45

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Check prices for these dates

Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
In one month
Apr 25 - Apr 27
In two months
May 23 - May 25

Browse Select Countryside B&B

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (538)
"Very cool place. For a come and go place for me it was perfect. I never saw anyone on the property."
The price is CA $62
CA $130 total
includes taxes & fees
Mar 31 - Apr 1
The Villa Toscana
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (169)
"Was surprisingly excellent "
The price is CA $277
CA $312 total
includes taxes & fees
Apr 21 - Apr 22
The Publishing House B&B
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (343)
"This used to be Ray's photo studio, because he was a professional photographer. That probably wouldn't matter to most people, but I am also a professional photographer and I really enjoyed talking with Ray about birds and his travels. I really appreciated the indoor parking, and the breakfasts were very large. The staff was very friendly and helpful in explaining everything that we had access to in the building. It would be a great stop for kids because of all the games available. Loved...
The price is CA $241
CA $272 total
includes taxes & fees
Mar 31 - Apr 1
Ray's Bucktown B&B
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.0 out of 10, Very good, (25)
"We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!"
The price is CA $45
CA $103 total
includes taxes & fees
Apr 3 - Apr 4
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (449)
"This bed and breakfast was an absolutely breathtaking gem that surpassed every expectation we had, delivering an experience that went well beyond what the photographs could capture. From the moment we arrived, we were struck by the stunning beauty of the place, which seemed to offer everything one could possibly desire in a cozy getaway. The owners were the epitome of hospitality—warm, welcoming, and genuinely sweet—always ready to lend a hand with anything we needed, whether it was local...
The price is CA $204
CA $240 total
includes taxes & fees
Apr 3 - Apr 4
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (241)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is CA $311
CA $365 total
includes taxes & fees
Apr 2 - Apr 3
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"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 $346 total
includes taxes & fees
Apr 2 - Apr 3
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (109)
"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 $331
CA $367 total
includes taxes & fees
Mar 31 - Apr 1
Harvey House Bed & Breakfast
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 $360 total
includes taxes & fees
Mar 31 - Apr 1
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, (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 $320
CA $465 total
includes taxes & fees
Apr 29 - Apr 30
House 5863 - Chicago Bed and Breakfast
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 $122
CA $250 total
includes taxes & fees
Mar 31 - Apr 1
Dubois Guest House Room 201
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is CA $106
CA $231 total
includes taxes & fees
Mar 31 - Apr 1
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 $112
CA $238 total
includes taxes & fees
Apr 22 - Apr 23
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is CA $120
CA $247 total
includes taxes & fees
Apr 1 - Apr 2
Dubois Guest House Room 101
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is CA $122
CA $250 total
includes taxes & fees
Mar 31 - Apr 1
Dubois Guest House Room 202
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is CA $122
CA $250 total
includes taxes & fees
Mar 31 - Apr 1
Villa Dubois Guest House Room 4
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is CA $122
CA $250 total
includes taxes & fees
Mar 31 - Apr 1
Villa Dubois Guest House Room 2
Room in Town house Rogers Park
Smart TV

Room in Town house Rogers Park

Room in Town house Rogers Park
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is CA $147
CA $281 total
includes taxes & fees
Mar 31 - Apr 1
Dubois Guest House Room 203
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is CA $206
CA $360 total
includes taxes & fees
Mar 31 - Apr 1
Wrigleyville Suites Room 3
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, (706)
"Our family celebrated Christmas at this hotel. It was beautiful and clean. I will definitely stay here again."
The price is CA $169
CA $241 total
includes taxes & fees
Apr 1 - Apr 2
Sentral Michigan Avenue
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, (453)
"As advertised. Would stay again. "
The price is CA $139
CA $164 total
includes taxes & fees
Apr 20 - Apr 21
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (267)
"It was good. Booking, arrival, and departure were easy. Bed was ok. Everything was clean and smelled nice. Parking was not easy and had to walk quite a distance. I don’t recall seeing that being the case when booking. "
The price is CA $153
CA $179 total
includes taxes & fees
Apr 20 - Apr 21
Sonder Market Hall
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 Navy Pier 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. Michigan Avenue and Navy Pier 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.