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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Ray's Bucktown B&B
Front of property

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 HK$1,704
HK$1,924 total
includes taxes & fees
10 Aug - 11 Aug
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (250)
"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, (465)
"Excellent location. Beautiful property, extremely clean."
The price is HK$1,677
HK$1,968 total
includes taxes & fees
12 Aug - 13 Aug
The Sono Chicago
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 HK$1,244
HK$1,404 total
includes taxes & fees
4 Sept - 5 Sept
The Publishing House B&B
Harvey House Bed & Breakfast
Property entrance

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 HK$2,057
HK$2,354 total
includes taxes & fees
11 Aug - 12 Aug
Harvey House Bed & Breakfast
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is HK$1,060
HK$1,858 total
includes taxes & fees
12 Aug - 13 Aug
Villa Dubois Guest Room 6
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is HK$742
HK$1,476 total
includes taxes & fees
7 Aug - 8 Aug
Dubois Guest House Room 101
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 HK$742
HK$1,476 total
includes taxes & fees
7 Aug - 8 Aug
Dubois Guest House Room 201
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is HK$1,060
HK$1,916 total
includes taxes & fees
8 Aug - 9 Aug
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 HK$1,325
HK$2,282 total
includes taxes & fees
28 Aug - 29 Aug
Villa Dubois Guest House Room 2
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
The price is HK$530
HK$1,222 total
includes taxes & fees
7 Aug - 8 Aug
Dubois Guest House Room 202
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)
"Great location, close to Credit Union 1 amphlitheater and walking distance to a good breakfast spot. Quiet neighborhood and clean apartment. Perfect space for a girls’ getaway."
Rustic cottage-style condo within walking distance to downtown Homewood
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is HK$1,590
HK$2,610 total
includes taxes & fees
12 Aug - 13 Aug
Villa Dubois Guest House Room 1
Adorable bed & breakfast in Chicago2222
Pool

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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Top Crestwood Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Highly recommended "
Claudia 1-night trip
Posted 9 hours ago
Hyatt Regency Chicago

Frequently asked questions

Searching for B&Bs in Crestwood?
If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your holiday. When you want to explore some of the destination's attractions, Hollywood Park is worth a visit.
Why should you consider B&Bs instead of traditional hotels?
Every B&B has a unique charm — whether it's a comfy common area with a fireplace or a beautiful dining room, the little 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 city centre. Enjoy the rooftop terrace and fireplace in reception. 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 city centre. Enjoy the snack bar/deli and unique decor. 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.
What's the best time of year to stay at a B&B in Crestwood?
When you're dreaming of a escape to Crestwood, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Crestwood is 1187 mm.
What is there to do in Crestwood?
Travellers enjoy Crestwood for its restaurants and shopping. If you want to see 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 plan your excursions 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 city centre. Otherwise, look for flights into Chicago O'Hare International Airport (ORD), which is 23.2 mi (37.3 km) away. If you'd like to explore around the area, you may want a rental car for your journey.