Find a Bed and Breakfast in Crestwood from CA $233

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Check prices for these dates

Next weekend
May 15 - May 17
In two weeks
May 22 - May 24
In one month
Jun 5 - Jun 7
In two months
Jul 3 - Jul 5

Our top choices for Crestwood bed & breakfast

Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (203 reviews)
"Loved this place - little gem that you'd never notice from the street. Great breakfast and the beds were good too."
United States
Noah
The price is CA $411
CA $464 total
includes taxes & fees
May 20 - May 21
The Publishing House B&B
Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (508 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is CA $198
CA $233 total
includes taxes & fees
May 11 - May 12
The Sono Chicago
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (263 reviews)
"Adorable space, comfortable bed, friendly staff"
United States
Marie
The price is CA $301
CA $354 total
includes taxes & fees
May 11 - May 12
Wicker Park Inn
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (398 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is CA $230
CA $260 total
includes taxes & fees
May 13 - May 14
Ray's Bucktown B&B
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (124 reviews)
"The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha."
United States
Timothy
The price is CA $358
CA $397 total
includes taxes & fees
May 12 - May 13
Harvey House Bed & Breakfast
Fridge, microwave, oven, coffee/tea maker

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $684
CA $792 total
includes taxes & fees
Jun 9 - Jun 10
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

2/10 Terrible
"👎"
Erick 2-night trip
Posted 1 hour ago
Crowne Plaza Chicago West Loop by IHG

Find out more about Crestwood

Crestwood B&B information

Number of reviews
1,098
Accommodation
8 B&B
Lowest Price
CA $233
Highest Price
CA $792

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. The Publishing House B&B: 11 rooms. 16.1 mi (26 km) from the downtown core. Enjoy the free full breakfast and winery. 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. Wicker Park Inn: 11 rooms. 17.4 mi (28.1 km) from the heart of downtown.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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