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Check prices for these dates

Next weekend
7 Mar - 9 Mar
In two weeks
14 Mar - 16 Mar
In one month
28 Mar - 30 Mar
In two months
25 Apr - 27 Apr

Compare 26 B&B in Countryside with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (532)
"Will stay again"
The price is AED 176
AED 354 total
includes taxes & fees
3 Mar - 4 Mar
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (21)
"Was having surgery but was canceled so I didn’t get to stay very long but would definitely stay again"
The price is AED 162
AED 319 total
includes taxes & fees
2 Mar - 3 Mar
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (444)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 480
AED 564 total
includes taxes & fees
4 Mar - 5 Mar
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (167)
"Was surprisingly excellent "
The price is AED 575
AED 649 total
includes taxes & fees
9 Mar - 10 Mar
The Publishing House B&B
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 AED 829
AED 974 total
includes taxes & fees
28 Feb - 1 Mar
Wicker Park Inn
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (341)
"This B&B is a gem. Loved it. It’s like staying in someone’s huge, comfortable home with a fabulous hostess. Plenty of parking, creative decor, and the huge made to order breakfast is fabulous. They have snacks, homemade baked goods and all kinds of drinks in the kitchen. They serve breakfast until 11 for late risers. Laundry, sauna, steam room. Will definitely stay again."
The price is AED 639
AED 721 total
includes taxes & fees
28 Feb - 1 Mar
Ray's Bucktown 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, (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 744
AED 1,098 total
includes taxes & fees
11 Mar - 12 Mar
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (108)
"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
3 Mar - 4 Mar
Harvey House Bed & Breakfast
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 AED 756
AED 888 total
includes taxes & fees
3 Mar - 4 Mar
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 AED 296
AED 620 total
includes taxes & fees
28 Feb - 1 Mar
Wrigleyville Suites Room 1
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 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 248
AED 563 total
includes taxes & fees
28 Feb - 1 Mar
Dubois Guest House Room 101
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
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 AED 248
AED 563 total
includes taxes & fees
8 Mar - 9 Mar
Dubois Guest House Room 201
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 436
AED 789 total
includes taxes & fees
22 Mar - 23 Mar
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is AED 248
AED 563 total
includes taxes & fees
28 Feb - 1 Mar
Villa Dubois Guest House Room 2
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is AED 248
AED 563 total
includes taxes & fees
28 Feb - 1 Mar
Villa Dubois Guest House Room 5
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is AED 248
AED 563 total
includes taxes & fees
28 Feb - 1 Mar
Dubois Guest House Room 202
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 296
AED 620 total
includes taxes & fees
28 Feb - 1 Mar
Wrigleyville Suites Room 2
Charming 3 bedrooms Apartment at the Medical District
Smart TV

Charming 3 bedrooms Apartment at the Medical District

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great host, great place, great location."
Charming 3 bedrooms Apartment at the Medical District
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, (684)
"it was alright, $77 extra for parking, no breakfast included but it was like a little apartment. no fan for guests either. no phone for communication but u can text their number yet they take forever to respond. "
The price is AED 465
AED 654 total
includes taxes & fees
9 Mar - 10 Mar
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, (433)
"Great location, nice looking place, not the most quality furniture but got the job done for a great price! I’d stay again "
The price is AED 339
AED 398 total
includes taxes & fees
23 Mar - 24 Mar
Sonder South Wabash
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is AED 493
AED 578 total
includes taxes & fees
5 Mar - 6 Mar
Found Chicago powered by Sonder
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, Soldier Field and Michigan Avenue 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. The Publishing House B&B: 11 rooms. Situated 14.1 mi (22.7 km) from the heart of Countryside. Enjoy the free full breakfast and winery. Wicker Park Inn: 11 rooms. 14.4 mi (23.2 km) from the heart of downtown.Ray’s Bucktown B&B: 11 rooms. Located 14.7 mi (23.7 km) from the core of Countryside. Enjoy the free cooked breakfast and rooftop terrace.
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. 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?
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.