A serene lake with reflections of trees and a cloudy sky.

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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

Our top choices for Crestwood bed & breakfast

Staircase

1. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (211 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is AED 892
AED 1,007 total
includes taxes & fees
23 Aug - 24 Aug
The Publishing House B&B
Private kitchen

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (538 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is AED 680
AED 798 total
includes taxes & fees
9 Aug - 10 Aug
The Sono Chicago
Property entrance

3. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (132 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is AED 995
AED 1,105 total
includes taxes & fees
17 Aug - 18 Aug
Harvey House Bed & Breakfast
Spa

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (412 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is AED 698
AED 788 total
includes taxes & fees
9 Aug - 10 Aug
Ray's Bucktown B&B
Property entrance

5. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (278 reviews)
"clean room, staff was helpful. We enjoyed our stay."
United States
Maggie
The price is AED 1,132
AED 1,329 total
includes taxes & fees
31 Aug - 1 Sep
Wicker Park Inn
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Loved the games for kids in the lobby!"
Paula 2-night trip
Posted less than an hour ago
Hilton Chicago

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. Wicker Park Inn: 11 rooms. 17.4 mi (28.1 km) from the downtown core. Ray's Bucktown B&B: 11 rooms. Situated 18.3 mi (29.5 km) from the heart of Crestwood. Enjoy the free cooked breakfast and rooftop terrace. The Publishing House B&B: 11 rooms. 16.1 mi (26 km) from the heart of downtown. Enjoy the free full breakfast and winery. Harvey House Bed & Breakfast: 5 rooms. Located 15.7 mi (25.2 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.

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