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

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Check prices for these dates

Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept
In one month
2 Oct - 4 Oct
In two months
30 Oct - 1 Nov

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, (213 reviews)
"This was such a perfect place to stay and I'll definitely stay here whenever going to Chicago. It was close enough to downtown to make it easy to access, but far enough away to be out of the hustle and bustle. The staff were all friendly and kind, the room was beautiful, the bed was very comfy, and the whole place had such a fun vibe and great decor. Breakfast was tasty and the menu options felt like something you'd order at your favorite fancy brunch spot, with fruit and pastries to round it...
United States
Julie
The price is HK$1,746
HK$1,972 total
includes taxes & fees
7 Sept - 8 Sept
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, (548 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 HK$1,153
HK$1,353 total
includes taxes & fees
7 Sept - 8 Sept
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, (133 reviews)
"This was one of the best B&B properties I’ve ever stayed in. The owner, Beth, was so friendly and accommodating. The room was spacious and so comfortable, and we had a delightful breakfast in the morning that featured bread and pastries from local bakeries. We wished we could stay longer! Highly recommend this charming property!"
United States
Monica
The price is HK$2,125
HK$2,358 total
includes taxes & fees
7 Sept - 8 Sept
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, (413 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is HK$1,355
HK$1,529 total
includes taxes & fees
7 Sept - 8 Sept
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, (281 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is HK$2,347
HK$2,755 total
includes taxes & fees
7 Sept - 8 Sept
Wicker Park Inn
Private kitchen

6. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is HK$3,426
HK$3,910 total
includes taxes & fees
28 Sept - 29 Sept
Pristine Apartment with Free Street Parking
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Very fancy, clean and the best view to the river. Staff was excellent!"
Candy 1-night trip
Posted 2 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Crestwood

Crestwood B&B information

Number of reviews
759
Accommodation
8 B&B
Lowest Price
HK$1,353
Highest Price
HK$3,910

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: The Sono Chicago: 7 rooms. 18 mi (29 km) from the heart of Crestwood. Enjoy the rooftop terrace and fireplace in reception. Ray's Bucktown B&B: 11 rooms. 18.3 mi (29.5 km) from the city centre. Enjoy the free cooked breakfast and rooftop terrace. 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 (25.2 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.

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