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

Book Crestwood Bed & Breakfast

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Crestwood bed & breakfast

A patio with a grill, outdoor seating, and potted plants.

1. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (422 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
$190 nightly
The price is $215
Oct 25 - Oct 26
Total with taxes and fees
Ray's Bucktown B&B
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (569 reviews)
"I like that it had a balcony food choice wasn’t my type of style end up ordering food off of site but definitely had all the amenities for you to be ready for the next day. Will be staying again little bit pricey for a short weekend stay but I will definitely be coming back. Very great part of the town hope to own my own own home in this place one day."
United States
Tavarion
$136 nightly
The price is $160
Nov 3 - Nov 4
Total with taxes and fees
The Sono Chicago
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

3. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (137 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
$258 nightly
The price is $286
Nov 5 - Nov 6
Total with taxes and fees
Harvey House Bed & Breakfast
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

4. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (221 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
$243 nightly
The price is $274
Nov 1 - Nov 2
Total with taxes and fees
The Publishing House B&B
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

5. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (286 reviews)
"Loved the location"
United States
Mary
$294 nightly
The price is $345
Oct 28 - Oct 29
Total with taxes and fees
Wicker Park Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

6. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
$382 nightly
The price is $393
Oct 27 - Oct 28
Total with taxes and fees
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

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Great one night stay. Staff was so nice and attentive. Room was very clean. Bed and pillows were comfortable. Overall great stay."
Annilie 1-night trip
Posted less than an hour ago
L7 Chicago by LOTTE

Find out more about Crestwood

Crestwood B&B information

Number of reviews
1,066
Accommodation
7 B&B
Lowest Price
$160
Highest Price
$393

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Crestwood?
Prices for B&Bs in Crestwood often vary, but you can find a great deal from $160 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Crestwood B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Crestwood?
The best time to book a B&B in Crestwood is during the vibrant spring months of May through July, when the region comes alive with outdoor activities and cultural events. This peak season attracts travelers who appreciate the lush landscapes and the variety of experiences that Crestwood has to offer. With temperatures ranging from the mid-50s to the high 80s Fahrenheit, visitors can enjoy comfortable weather while indulging in hiking, biking, and exploring the charming local attractions.

July stands out as the most popular month to visit, making it an ideal time for those looking to soak in the lively atmosphere. Many travelers flock to Crestwood for its beautiful parks and engaging community events, creating a superb backdrop for both relaxation and adventure. Whether you're wandering through the picturesque trails or enjoying a picnic in one of the many green spaces, the allure of summer in Crestwood is undeniable.

If you're seeking a more budget-friendly option, consider planning your visit in November. This time of year offers a quieter experience, allowing you to appreciate the serene beauty of Crestwood without the hustle and bustle of peak tourist traffic. You can enjoy the crisp autumn air and take part in local seasonal festivities, which can provide a unique glimpse into the community's culture.
What is the difference between a Crestwood Bed and Breakfast and a hotel?
Every Crestwood B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Crestwood B&Bs.

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