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Check prices for these dates

Next weekend
12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

B&B in Countryside

Our top choices for Countryside bed & breakfast

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (67)
"Very friendly and helpful staff. Rooms and bathrooms are very clean. I enjoyed my stay., it was cozy and comfortable. I would definitely stay at Dorothys again if I am back in the area.. I would also recommend it to friends meeting to stay near Wrigley or downtown."
The price is AED 303
AED 484 total
includes taxes & fees
15 Sep - 16 Sep
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (594)
"Was a great stay!"
The price is AED 221
AED 407 total
includes taxes & fees
3 Sep - 4 Sep
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (371)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is AED 619
AED 699 total
includes taxes & fees
2 Sep - 3 Sep
Ray's Bucktown B&B
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is AED 750
AED 847 total
includes taxes & fees
21 Sep - 22 Sep
The Publishing House B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (479)
"Everything was taken care of! A wonderful stay. "
The price is AED 444
AED 724 total
includes taxes & fees
2 Sep - 3 Sep
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (251)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (470)
"Loved the shared kitchen access! "
The price is AED 573
AED 673 total
includes taxes & fees
2 Sep - 3 Sep
The Sono Chicago
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is AED 962
AED 1,068 total
includes taxes & fees
2 Sep - 3 Sep
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (106)
"Would stay again anytime!!"
The price is AED 967
AED 1,135 total
includes taxes & fees
1 Oct - 2 Oct
Villa D' Citta
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, (147)
"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!
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 298
AED 631 total
includes taxes & fees
2 Sep - 3 Sep
Villa Dubois Guest Room 6
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 338
AED 680 total
includes taxes & fees
3 Sep - 4 Sep
Wrigleyville Suites Room 3
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 338
AED 680 total
includes taxes & fees
3 Sep - 4 Sep
Wrigleyville Suites Room 1
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 298
AED 631 total
includes taxes & fees
2 Sep - 3 Sep
Dubois Guest House Room 101
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is AED 298
AED 631 total
includes taxes & fees
3 Sep - 4 Sep
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 298
AED 631 total
includes taxes & fees
2 Sep - 3 Sep
Villa Dubois Guest House Room 2
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is AED 298
AED 631 total
includes taxes & fees
2 Sep - 3 Sep
Villa Dubois Guest House Room 4
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
The price is AED 298
AED 631 total
includes taxes & fees
2 Sep - 3 Sep
Dubois Guest House Room 202
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

The price is AED 353
AED 697 total
includes taxes & fees
3 Sep - 4 Sep
Wrigleyville Suites Room 5
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 338
AED 680 total
includes taxes & fees
3 Sep - 4 Sep
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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Top Countryside Hotel Reviews

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: Dorothy's: 7 rooms. 17.1 mi (27.6 km) from the heart of Countryside.The Villa Toscana: 9 rooms. 17.1 mi (27.6 km) from the downtown core. Ray's Bucktown B&B: 11 rooms. 14.7 mi (23.7 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. 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.