Westchester B&B: Find the Best Bed and Breakfast from CA $123

Q: 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 downtown core. The Sono Chicago : 7 rooms. Situated 13 mi (20.9 km) from the heart of Westchester. Enjoy the rooftop terrace and fireplace in the lobby. House 5863 - Chicago Bed and Breakfast : 7 rooms. 14.7 mi (23.6 km) from the heart of downtown. Enjoy the designer toiletries and private yard. 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.

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Our top choices for Westchester bed & breakfast

The Publishing House B&B

Downtown Chicago

STEVEN

CA $306 total

includes taxes & fees

Mar 31 - Apr 1

The Sono Chicago

Near North Side

Catie

CA $192 total

includes taxes & fees

Mar 30 - Mar 31

Dorothy's

Lakeview

Winter Fox

CA $123 total

includes taxes & fees

Mar 29 - Mar 30

Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

Lakeview

Rico

CA $133 total

includes taxes & fees

Mar 30 - Mar 31

Ray's Bucktown B&B

Bucktown

Matthew

CA $261 total

includes taxes & fees

Apr 2 - Apr 3

Villa D' Citta

Lincoln Park

Earl

CA $332 total

includes taxes & fees

Apr 20 - Apr 21

Wicker Park Inn

West Town

Michael

House 5863 - Chicago Bed and Breakfast

Edgewater

James

CA $293 total

includes taxes & fees

Mar 30 - Mar 31

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Top Westchester Hotel Reviews

Eurostars Magnificent Mile

8/10 Good

"I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean! "

Hilton Chicago

10/10 Excellent

"We loved our stay. Two adults and our eight-year-old son took a weekend trip to Chicago. This hotel was very close to the field museum and walking distance to magnificent mile. Short Uber ride to nearby shopping and Willis Tower. The staff were awesome and upgraded our room at a low price. We felt very safe and staff were very helpful. The eighth floor had a beautiful pool, spa and sauna, great view of lake mi, open late too. We dined for breakfast at yoke and Niu B for dinner. Delicious. At checkout we purchased a future Hilton grand vacation at a great discount too. Let’s go. :)"

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"Lobby is beautiful and the check in was smooth; however the room was not great. Dingy, dated, poorly set up- only outlet by the bed was connected to the large, blaring overhead light, so once turned off the outlet stopped functioning. Bathroom was dated and cramped with min counter space. Sheets did not fit bed and peeled off throughout the night. Just generally a very mediocre room for the price."

Find out more about Westchester

Westchester B&B information

Number of reviews	1,937
Accommodation	12 B&B
Lowest Price	CA $123
Highest Price	CA $352

Frequently asked questions

Searching for B&Bs in Westchester?

Whether you're on a family vacation and want a small, cozy place to stay, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. If you're interested in discovering some top attractions, Wrigley Field and Michigan Avenue are worth a stop.

Why consider B&Bs instead of traditional hotels?

With attentive service, opportunities to mingle with other guests, and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind 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 downtown core. The Sono Chicago: 7 rooms. Situated 13 mi (20.9 km) from the heart of Westchester. Enjoy the rooftop terrace and fireplace in the lobby. House 5863 - Chicago Bed and Breakfast: 7 rooms. 14.7 mi (23.6 km) from the heart of downtown. Enjoy the designer toiletries and private yard. 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 temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.

What is there to do in Westchester?

Travelers enjoy Westchester for its restaurants and shopping. You might also consider a trip to sites like 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 map out your trip 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 from the heart of the city. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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