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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured B&B in Westchester

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very good, (63)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
The price is RM295
RM494 total
includes taxes & fees
7 Sept - 8 Sept
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (589)
"Was a great stay!"
The price is RM345
RM575 total
includes taxes & fees
13 Aug - 14 Aug
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (369)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is RM805
RM908 total
includes taxes & fees
14 Aug - 15 Aug
Ray's Bucktown B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (478)
"Everything was taken care of! A wonderful stay. "
The price is RM579
RM920 total
includes taxes & fees
18 Aug - 19 Aug
House 5863 - Chicago Bed and Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is RM881
RM994 total
includes taxes & fees
2 Sept - 3 Sept
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (250)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (115)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is RM1,109
RM1,270 total
includes taxes & fees
14 Aug - 15 Aug
Harvey House Bed & Breakfast
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (466)
"Loved the shared kitchen access! "
The price is RM833
RM978 total
includes taxes & fees
18 Aug - 19 Aug
The Sono Chicago
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
The price is RM969
RM1,137 total
includes taxes & fees
13 Aug - 14 Aug
Villa D' Citta
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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Frequently asked questions

Searching for B&Bs in Westchester?
Whether you're on a romantic holiday and want to stay somewhere quiet, or you're travelling solo and hoping to get some tips from locals, a B&B can be a good choice for many different types of travellers. If you're interested in discovering some top attractions, Wrigley Field and Michigan Avenue are worth a visit.
Why should you consider a B&B over a traditional hotel room?
With attentive service, opportunities to meet other guests and breakfast served on site, B&Bs offer a unique environment.
What are the best B&Bs in Westchester?
Here are some well-liked B&Bs in the area: Dorothy's: 7 rooms. 13.6 mi (21.9 km) from the heart of Westchester. The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the city centre. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 14.7 mi (23.6 km) from the heart of Westchester. Enjoy the designer toiletries and private garden. Ray's Bucktown B&B: 11 rooms. 11.3 mi (18.2 km) from the city centre. Enjoy the free cooked breakfast and rooftop terrace. The Publishing House B&B: 11 rooms. Located 11.8 mi (19 km) from the core of Westchester. Enjoy the free full breakfast and winery.
What's the best time of year to book my B&B in Westchester?
When you're planning your getaway to Westchester, year-round temperatures and rainfall may be important factors to consider. 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. The snowiest months in Westchester are January, November, February and December, with each month seeing an average of 13 cm of snowfall.
What is there to do in Westchester?
Travellers enjoy Westchester for its restaurants and shopping. You might also consider a trip to sites such as Wrigley Field or Michigan Avenue if you have time to see more of the area.
How can I get to and around Westchester?
You can plan your excursions in and around Westchester ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) away. Otherwise, look for flights into Chicago O'Hare International Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, consider renting a car to explore more sights.