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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sep - 21 Sep

B&B in Crestwood

Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (368)
"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 AED 698
AED 788 total
includes taxes & fees
29 Jul - 30 Jul
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

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
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 AED 798
AED 937 total
includes taxes & fees
4 Aug - 5 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 AED 753
AED 850 total
includes taxes & fees
20 Aug - 21 Aug
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, (112)
"Enjoyed my short stay. Wish I could have spent more time here! Quiet, peaceful, safe, and comfortable. I travel frequently for work and this is by far, one of the best experiences I have had. Thank you Beth!"
The price is AED 962
AED 1,102 total
includes taxes & fees
4 Aug - 5 Aug
Harvey House Bed & Breakfast
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 496
AED 877 total
includes taxes & fees
11 Aug - 12 Aug
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is AED 620
AED 1,034 total
includes taxes & fees
28 Jul - 29 Jul
Villa Dubois Guest House Room 4
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 620
AED 1,034 total
includes taxes & fees
28 Jul - 29 Jul
Dubois Guest House Room 201
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 620
AED 1,034 total
includes taxes & fees
28 Jul - 29 Jul
Dubois Guest House Room 101
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is AED 620
AED 1,022 total
includes taxes & fees
28 Jul - 29 Jul
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is AED 744
AED 1,199 total
includes taxes & fees
28 Jul - 29 Jul
Dubois Guest House Room 203
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 AED 744
AED 1,199 total
includes taxes & fees
28 Jul - 29 Jul
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Close to most attractions"
Katrina 3-night trip
Posted 8 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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.