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

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Check prices for these dates

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9
In one month
Aug 21 - Aug 23
In two months
Sep 18 - Sep 20

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, (208 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is NT$10,085
NT$11,384 total
includes taxes & fees
Aug 19 - Aug 20
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, (530 reviews)
"Really great spot , nice room and parking was easy :)"
United States
AnjolaOluwa
The price is NT$6,123
NT$7,187 total
includes taxes & fees
Jul 28 - Jul 29
The Sono Chicago
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (129 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
The price is NT$8,746
NT$9,706 total
includes taxes & fees
Aug 17 - Aug 18
Harvey House Bed & Breakfast
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (408 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is NT$6,682
NT$7,544 total
includes taxes & fees
Jul 27 - Jul 28
Ray's Bucktown B&B
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (274 reviews)
"Nice place to stay in an historic neighborhood"
United States
Linda
The price is NT$8,770
NT$10,295 total
includes taxes & fees
Aug 11 - Aug 12
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"We really enjoyed our stay here. The location is great. It’s right next to the Riverwalk. It’s also walkable to Navy Pier. The room was very clean."
Krista 2-night trip
Posted less than an hour ago
Hyatt Regency Chicago

Find out more about Crestwood

Crestwood B&B information

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 B&B
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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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