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

Search B&B in Crestwood

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

Our top choices for Crestwood bed & breakfast

Property entrance

1. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (135 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is AED 1,075
AED 1,193 total
includes taxes & fees
22 Sep - 23 Sep
Harvey House Bed & Breakfast
Private kitchen

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (555 reviews)
"It was a very comfortable hotel. We loved the free street parking, easy access to public transportation, coffee, breakfast, bottled water, bubbly water and snacks. I will stay here again!"
United States
Christie
The price is AED 859
AED 1,009 total
includes taxes & fees
30 Sep - 1 Oct
The Sono Chicago
Spa

3. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (415 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is AED 678
AED 766 total
includes taxes & fees
28 Sep - 29 Sep
Ray's Bucktown B&B
Staircase

4. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (216 reviews)
"Gorgeous building inside and out. Beautiful clean rooms. Amazing public spaces. Breakfast was by far one of the best meals of the whole trip."
United States
Mollie
The price is AED 1,155
AED 1,304 total
includes taxes & fees
27 Sep - 28 Sep
The Publishing House B&B
Property entrance

5. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (283 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is AED 1,166
AED 1,368 total
includes taxes & fees
28 Sep - 29 Sep
Wicker Park Inn
Coffee/tea maker, fridge, microwave, oven

6. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is AED 1,398
AED 1,620 total
includes taxes & fees
20 Oct - 21 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Crestwood Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Accessibility!"
Christopher 3-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

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

Explore a world of travel with Expedia