Photo by Monica Ferro

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Browse Select Countryside B&B

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (548)
"Super cute house! Very detailed directions on check in, super easy excellent neighbourhood!"
The price is £84
includes taxes & fees
4 May - 5 May
The Villa Toscana
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (171)
"Amazing stay! Great location and beautiful hotel that made you feel cozy"
The price is £185
includes taxes & fees
26 May - 27 May
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, (348)
"What a rad spot...great staff, A M A Z I N G breakfast (can I say Nutella and banana stuffed French toast?!), nice sauna on premise, clean rooms, so much to look at, and I parked in the garage! Will be back...daughters had a blast. "
The price is £143
includes taxes & fees
3 May - 4 May
Ray's Bucktown B&B
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.0 out of 10, Very good, (31)
"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 £68
includes taxes & fees
4 May - 5 May
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (452)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is £133
includes taxes & fees
11 May - 12 May
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"The Wicker Park Inn was located close to many transportation options. The breakfast room was bright and sunny with good light breakfast options."
The price is £243
includes taxes & fees
5 May - 6 May
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Wonderful place. "
The price is £202
includes taxes & fees
19 May - 20 May
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Awesome, comfortable stay good food options would recommend "
The price is £218
includes taxes & fees
26 May - 27 May
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 £194
includes taxes & fees
4 May - 5 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, (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 £216
includes taxes & fees
6 May - 7 May
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 £220
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 201
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is £184
includes taxes & fees
4 May - 5 May
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 £184
includes taxes & fees
4 May - 5 May
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is £220
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 101
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is £220
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 202
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is £220
includes taxes & fees
3 May - 4 May
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 £220
includes taxes & fees
3 May - 4 May
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is £254
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 203
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is £194
includes taxes & fees
4 May - 5 May
Wrigleyville Suites Room 3
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 £194
includes taxes & fees
4 May - 5 May
Wrigleyville Suites Room 2
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, (739)
"Great family place to stay. "
The price is £149
includes taxes & fees
26 May - 27 May
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (487)
"Great stay "
The price is £96
includes taxes & fees
26 May - 27 May
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (277)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is £115
includes taxes & fees
26 May - 27 May
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 passing through town and are looking for accommodation that’s small and charming, or you’re travelling solo and hoping to get some tips from locals, B&Bs can be a great choice for many types of holidaymakers. If you’re interested in discovering some top attractions, Soldier Field and Michigan Avenue are worth a visit.
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 cosy reading space or a sunlit breakfast nook, the tiny details are what make bed and breakfasts a home away from home.
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 city centre. 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. Wicker Park Inn: 11 rooms. 14.4 mi (23.2 km) from the city centre. The Sono Chicago: 7 rooms. Located 15.7 mi (25.3 km) from the core of Countryside. Enjoy the rooftop terrace and fireplace in reception.
When should I book my B&B in Countryside?
When you’re planning your escape to Countryside, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Countryside is 1236 mm.
What is there to do in Countryside?
Travellers 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?
You can map out your trip in and around Countryside ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 7.3 mi (11.8 km) away. You can also search for flights into Chicago O’Hare International 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.