Book Westchester Bed & Breakfast

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Compare 12 B&B in Westchester with updated reviews, rates, and availability.

Other property types in Westchester

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 426 reviews
"Property was beautiful and well kept. Room was comfortable and felt like home. The pool was disappointing and much smaller than it appears. Communication during check in and valets could be better. "
The price is $199
$263 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, 94 reviews
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is $100
$117 total
includes taxes & fees
Jun 30 - Jul 1
Sonder Market Hall
Sonder South Wabash
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 309 reviews
"Sonder rocks!"
The price is $196
$230 total
includes taxes & fees
Jul 2 - Jul 3
Sonder South Wabash
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.

Westchester B&B information

Number of reviews
2,429
Accommodation
12 B&B
Lowest Price
$61
Highest Price
$262

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 Navy Pier 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: Old Chicago Inn: 10 rooms. 13.2 mi (21.3 km) from the heart of Westchester. Enjoy the free full breakfast and fireplace in the lobby. The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the downtown core. Ray’s Bucktown B&B: 11 rooms. Situated 11.3 mi (18.2 km) from the heart of Westchester. Enjoy the free cooked breakfast and rooftop terrace. 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. Wicker Park Inn: 11 rooms. Located 11.4 mi (18.3 km) from the core of Westchester.
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 Navy Pier 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.

Recent reviews of Westchester hotels
Expedia verified reviews

InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

5/5 Excellent
"Great location. Lobby is suffering from lack of seating but overall a nice hotel. "
A verified traveler stayed at InterContinental Chicago Magnificent Mile, an IHG Hotel
Posted 9 hours ago
InterContinental Chicago Magnificent Mile, an IHG Hotel