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Check prices for these dates

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Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

B&B in Crestwood

Ray's Bucktown B&B
Experience the charm of this historic building, featuring a welcoming entrance, lush garden, and large windows offering views of the surrounding area.

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (369)
"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 NT$5,535
NT$6,248 total
includes taxes & fees
Aug 5 - Aug 6
Ray's Bucktown B&B
Wicker Park Inn
Welcome to The Wicker Park Inn, a charming urban B&B located at 1329 N. Wicker Park.

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (249)
"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
Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
The price is NT$5,539
NT$6,502 total
includes taxes & fees
Aug 6 - Aug 7
The Sono Chicago
The Publishing House B&B
Staircase leads to an upper level with potted plants and decorative shelves.

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 NT$4,749
NT$5,361 total
includes taxes & fees
Sep 4 - Sep 5
The Publishing House B&B
Harvey House Bed & Breakfast
Enter a classic space with a traditional feel, featuring a dresser, lamp, and ornate rug.

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (114)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is NT$7,853
NT$8,990 total
includes taxes & fees
Aug 11 - Aug 12
Harvey House Bed & Breakfast
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 Crestwood Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"The room and bathroom were both spacious with high ceilings. Great view on the lake side. "
Madison 2-night trip
Posted 9 hours ago
Congress Plaza Hotel

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: Ray's Bucktown B&B: 11 rooms. 18.3 mi (29.5 km) from the heart of Crestwood. Enjoy the free cooked breakfast and rooftop terrace. The Sono Chicago: 7 rooms. 18 mi (29 km) from the downtown core. Enjoy the rooftop terrace and fireplace in the lobby. Wicker Park Inn: 11 rooms. Situated 17.4 mi (28.1 km) from the heart of Crestwood. Harvey House Bed & Breakfast: 5 rooms. 15.7 mi (25.3 km) from the heart of downtown. Enjoy the deli and unique décor. The Publishing House B&B: 11 rooms. Located 16.1 mi (26 km) from the core of Crestwood. Enjoy the free full breakfast and winery.
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.