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Compare 28 B&B in Countryside with updated reviews, rates, and availability.

The Villa Toscana
Lounge

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (508)
"Stayed here twice. Both times was problem free and just as I expected. Location is prime. "
The price is AED 191
AED 371 total
includes taxes & fees
12 Jan - 13 January 2025
The Villa Toscana
Dorothy's
Room

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (11)
"Love the coziness of the location and th area is nice and safe "
The price is AED 153
AED 308 total
includes taxes & fees
8 Jan - 9 January 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 AED 547
AED 617 total
includes taxes & fees
1 Jan - 2 January 2025
Ray's Bucktown B&B
The Sono Chicago
Room

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 AED 555
AED 652 total
includes taxes & fees
29 Dec - 30 Dec
The Sono Chicago
The Publishing House B&B
Fireplace

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 AED 583
AED 658 total
includes taxes & fees
23 Jan - 24 January 2025
The Publishing House B&B
Harvey House Bed & Breakfast
Interior

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 AED 848
AED 942 total
includes taxes & fees
30 Dec - 31 Dec
Harvey House Bed & Breakfast
Wicker Park Inn
Room

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 AED 672
AED 788 total
includes taxes & fees
5 Jan - 6 January 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 AED 520
AED 820 total
includes taxes & fees
1 Jan - 2 January 2025
House 5863 - Chicago Bed and Breakfast
Villa D' Citta
Front of property

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 AED 756
AED 888 total
includes taxes & fees
6 Jan - 7 January 2025
Villa D' Citta
Wrigleyville Suites Room 1
Bedroom with a queen-sized bed, patterned wallpaper, two windows with blinds, and a geometric rug on the floor.

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 275
AED 587 total
includes taxes & fees
26 Dec - 27 Dec
Wrigleyville Suites Room 1
Villa Dubois Guest Room 6
A cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.

Villa Dubois Guest Room 6

The price is AED 248
AED 555 total
includes taxes & fees
26 Dec - 27 Dec
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
A cozy and modern bedroom with brownish paper wall, a comfortable queen size bed, a large window with natural light, and stylish artwork.

Villa Dubois Guest House Room 5

The price is AED 248
AED 555 total
includes taxes & fees
26 Dec - 27 Dec
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
A simply furnished room with a plush armchair, a wooden table with and a framed painting on a blue ash paper wall.

Villa Dubois Guest House Room 2

The price is AED 248
AED 555 total
includes taxes & fees
26 Dec - 27 Dec
Villa Dubois Guest House Room 2
Dubois Guest House Room 101
Cozy bedroom with a patterned wallpaper wall, a queen sized bed with grey linens, a ceiling fan, a vanity area with a mirror and chair,and a window with white curtains.

Dubois Guest House Room 101

The price is AED 248
AED 555 total
includes taxes & fees
26 Dec - 27 Dec
Dubois Guest House Room 101
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dining Room

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
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is AED 248
AED 555 total
includes taxes & fees
26 Dec - 27 Dec
Dubois Guest House Room 201
Dubois Guest House Room 202
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.

Dubois Guest House Room 202

The price is AED 248
AED 555 total
includes taxes & fees
26 Dec - 27 Dec
Dubois Guest House Room 202
Rustic cottage-style condo within walking distance to downtown Homewood
Living area

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
A cozy and stylish bedroom with a comfortable bed, a patterned armchair, and a unique wall decoration.

Villa Dubois Guest House Room 4

The price is AED 248
AED 555 total
includes taxes & fees
26 Dec - 27 Dec
Villa Dubois Guest House Room 4
Dubois Guest House Room 203
Close view of bedroom with a patterned accent wall, a queen size bed with grey linens, a ceiling fan, a vanity area with a mirror and chair, and a window with white curtains.

Dubois Guest House Room 203

The price is AED 298
AED 614 total
includes taxes & fees
26 Dec - 27 Dec
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
Garden

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (629)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is AED 403
AED 581 total
includes taxes & fees
29 Dec - 30 Dec
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
Front of property

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (343)
"The property location was great. The room was very spacious. The only knock was there was not a tv in the bedroom."
Kasa Magnificent Mile Chicago
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"The stay was great."
The price is AED 456
AED 535 total
includes taxes & fees
15 Jan - 16 January 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.