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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Browse Select Crestwood B&B

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 Rp2.898.617
Rp3.272.282 total
includes taxes & fees
20 Aug - 21 Aug
Ray's Bucktown B&B
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 Rp3.504.728
Rp3.956.487 total
includes taxes & fees
7 Sept - 8 Sept
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (251)
"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
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is Rp4.236.278
Rp4.849.730 total
includes taxes & fees
21 Aug - 22 Aug
Harvey House Bed & Breakfast
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (467)
"Loved the shared kitchen access! "
The price is Rp2.444.753
Rp2.869.836 total
includes taxes & fees
25 Aug - 26 Aug
The Sono Chicago
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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"It’s a beautiful hotel with lovely staff. The beds were very comfy but the pillows have no neck support. We loved how close it was to Millennium park and how walkable the area was for finding dining options and seeing the sights. It’s only about one city block from the Art Institute and we got to walk by those beautiful lions every day. We did not try the restaurant but did have a drink at the Lockwood bar. The drinks were well balanced but it took forever to get drinks; I had to wait 15 minutes just to place my order at the bar with three bartenders. We didn’t see any waiters to help either. "
Tara 2-night trip
Posted 7 hours ago
Palmer House a Hilton Hotel

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. The Publishing House B&B: 11 rooms. Situated 16.1 mi (26 km) from the heart of Crestwood. Enjoy the free full breakfast and winery. Harvey House Bed & Breakfast: 5 rooms. 15.7 mi (25.3 km) from the city centre. Enjoy the snack bar/deli and unique decor. Wicker Park Inn: 11 rooms. Located 17.4 mi (28.1 km) from the core of Crestwood.
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.