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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 17 B&B in Crestwood with updated reviews, rates, and availability.

The Sono Chicago
Room

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (443)
"Our stay at The Sono was great! We were only staying a night and booked a queen room, and they gave us a free upgrade to a king room since it was unoccupied. The room was fantastic & clean, the breakfast was delicious with lots of variety and the voucher for free street parking made this the best option for our stay. I would definitely stay again."
The price is SAR 491
SAR 576 total
includes taxes & fees
18 Feb - 19 Feb
The Sono Chicago
The Publishing House B&B
Fireplace

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (166)
"Was surprisingly excellent "
The price is SAR 525
SAR 593 total
includes taxes & fees
27 Feb - 28 Feb
The Publishing House B&B
Wicker Park Inn
Room

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (240)
"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 SAR 686
SAR 805 total
includes taxes & fees
17 Feb - 18 Feb
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 SAR 652
SAR 736 total
includes taxes & fees
17 Feb - 18 Feb
Ray's Bucktown B&B
Harvey House Bed & Breakfast
Interior

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 SAR 866
SAR 962 total
includes taxes & fees
17 Feb - 18 Feb
Harvey House Bed & Breakfast
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 SAR 253
SAR 575 total
includes taxes & fees
17 Feb - 18 Feb
Dubois Guest House Room 101
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
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. "
Dubois Guest House Room 201
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

Villa Dubois Guest Room 6
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

Villa Dubois Guest House Room 2
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

Villa Dubois Guest House Room 5
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

Dubois Guest House Room 202
Charming 3 bedrooms Apartment at the Medical District
Living area

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
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

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

Dubois Guest House Room 203
Villa Dubois Guest House Room 1
King size bed, grey with blue wall paper design

Villa Dubois Guest House Room 1

Villa Dubois Guest House Room 1
Adorable bed & breakfast in Chicago2222
Point of interest

Adorable bed & breakfast in Chicago2222

Adorable bed & breakfast in Chicago2222
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 Crestwood

Sentral Michigan Avenue
Pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (679)
"I loved this place will be staying again! Love love loved it!"
The price is SAR 411
SAR 593 total
includes taxes & fees
18 Feb - 19 Feb
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (432)
"Was nice but noisy and around it was unsanitary "
The price is SAR 334
SAR 392 total
includes taxes & fees
9 Mar - 10 Mar
Sonder South Wabash
Sonder Market Hall
Living area

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (255)
"It was wonderful!"
The price is SAR 424
SAR 497 total
includes taxes & fees
9 Mar - 10 Mar
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 Crestwood?
If you’re looking for something a little more offbeat than your standard hotel experience, a bed and breakfast could be a great option for your trip. When you want to explore some of the destination’s attractions, Hollywood Park is worth a visit.
Why would you choose a B&B versus a traditional hotel?
B&Bs all have a unique charm. Whether it’s a cozy 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 bed and breakfasts in Crestwood?
Below are some well-liked B&Bs in the area: The Sono Chicago: 7 rooms. 18 mi (29 km) from the heart of Crestwood. Enjoy the rooftop terrace and fireplace in the lobby. The Publishing House B&B: 11 rooms. 16.1 mi (26 km) from the downtown core. Enjoy the free full breakfast and winery. Wicker Park Inn: 11 rooms. Situated 17.4 mi (28.1 km) from the heart of Crestwood. Ray’s Bucktown B&B: 11 rooms. 18.3 mi (29.5 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. Harvey House Bed & Breakfast: 5 rooms. Located 15.7 mi (25.3 km) from the core of Crestwood. Enjoy the deli and unique décor.
When should I stay at a B&B in Crestwood?
When you’re dreaming of a escape to Crestwood, be sure to take into account the year-round temperatures. 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 Crestwood is 47 inches.
What is there to do in Crestwood?
Travelers enjoy Crestwood for its restaurants and shopping. If you want to check out some popular attractions in Crestwood, you might enjoy a visit to Hollywood Park. Soldier Field and Gaelic Park are also some sites to visit if you want to see more of the area.
How can I get to and around Crestwood?
You can map out your trip in and around Crestwood ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.8 mi (14.2 km) away from the heart of the city. You can also search for flights into Chicago O’Hare Intl. Airport (ORD), which is 23.2 mi (37.3 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.