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Compare 25 B&B in Westchester with updated reviews, rates, and availability.

The Villa Toscana
Lounge
The Villa Toscana
2.5 star property
7.8 out of 10, Good, (494)
"Digital check in a little confusing but Brandon was on site and every person there was helpful. It is a big old BnB place. They had breakfast "
The price is AED 122
AED 290 total
includes taxes & fees
10 Nov - 11 Nov
The Villa Toscana
Old Chicago Inn
Property entrance
Old Chicago Inn
2.0 star property
7.4 out of 10, Good, (762)
"Wonderful alternative to usual hotel properties at comparable prices. "
Old Chicago Inn
House 5863 - Chicago Bed and Breakfast
Exterior
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (469)
"Cozy little place. The only adjustment I could make is have better options for breakfast like eggs and bacon and such. No complaints tho because it was still great to sleep in. Super clean"
The price is AED 491
AED 783 total
includes taxes & fees
10 Nov - 11 Nov
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Room
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (237)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is AED 883
AED 1,036 total
includes taxes & fees
12 Nov - 13 Nov
Wicker Park Inn
The Sono Chicago
Room
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (433)
"It was very clean and tidy. When we needed new towels they were there. Halfway through our stay everything was deep cleaned. The owners were extremely nice and offered a wide variety for breakfast. Any questions we had were answered quickly and effortlessly. Our room was cozy and the upstairs roof patio had a view that was beyond breathtaking. The place is close to downtown and in a good area to go anywhere in Chicago. "
The price is AED 520
AED 611 total
includes taxes & fees
12 Nov - 13 Nov
The Sono Chicago
Ray's Bucktown B&B
Front of property
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (328)
"Great stay. Clean and parking was easy. Breakfast was great and pet friendly "
The price is AED 584
AED 660 total
includes taxes & fees
11 Nov - 12 Nov
Ray's Bucktown B&B
Villa D' Citta
Front of property
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (93)
"Edith was amazing! She greeted us each morning with coffee, breakfast, and a smile😊 Except the last morning, a woman that introduced herself as the Asst Manager came in while we were eating and complained about the new coffee maker and was pretty unpleasant, but everything and everyone else was excellent!! "
The price is AED 756
AED 888 total
includes taxes & fees
2 Dec - 3 Dec
Villa D' Citta
The Publishing House B&B
Fireplace
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (160)
"This was the nicest stay I have had in years. Felt like a weekend with your best friend and they are an excellent host. Every amenity and design of the place is well intentioned and thought out. I will definitely be back!"
The price is AED 591
AED 676 total
includes taxes & fees
25 Nov - 26 Nov
The Publishing House B&B
Harvey House Bed & Breakfast
Interior
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (103)
"Awesome, comfortable stay good food options would recommend "
The price is AED 848
AED 942 total
includes taxes & fees
11 Nov - 12 Nov
Harvey House Bed & Breakfast
Dubois Guest House Room 201
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Dubois Guest House Room 201
6.0 out of 10, (2)
The price is AED 312
AED 632 total
includes taxes & fees
11 Nov - 12 Nov
Dubois Guest House Room 201
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dining Room
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
9.8 out of 10, Exceptional, (134)
"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa Dubois Guest House Room 2
A simply furnished room with a plush armchair, a wooden table with and a framed painting on a blue ash paper wall.
Villa Dubois Guest House Room 2
The price is AED 327
AED 650 total
includes taxes & fees
11 Nov - 12 Nov
Villa Dubois Guest House Room 2
Wrigleyville Suites Room 1
Bedroom with a queen-sized bed, patterned wallpaper, two windows with blinds, and a geometric rug on the floor.
Wrigleyville Suites Room 1
2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
The price is AED 528
AED 902 total
includes taxes & fees
10 Nov - 11 Nov
Wrigleyville Suites Room 1
Villa Dubois Guest Room 6
A cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Villa Dubois Guest Room 6
The price is AED 298
AED 614 total
includes taxes & fees
9 Dec - 10 Dec
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
A cozy and modern bedroom with brownish paper wall, a comfortable queen size bed, a large window with natural light, and stylish artwork.
Villa Dubois Guest House Room 5
The price is AED 298
AED 614 total
includes taxes & fees
11 Nov - 12 Nov
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
Cozy bedroom with a patterned wallpaper wall, a queen sized bed with grey linens, a ceiling fan, a vanity area with a mirror and chair,and a window with white curtains.
Dubois Guest House Room 101
The price is AED 293
AED 608 total
includes taxes & fees
11 Nov - 12 Nov
Dubois Guest House Room 101
Villa Dubois Guest House Room 4
A cozy and stylish bedroom with a comfortable bed, a patterned armchair, and a unique wall decoration.
Villa Dubois Guest House Room 4
The price is AED 312
AED 632 total
includes taxes & fees
11 Nov - 12 Nov
Villa Dubois Guest House Room 4
Charming 3 bedrooms Apartment at the Medical District
Living area
Charming 3 bedrooms Apartment at the Medical District
2.0 star property
10.0 out of 10, Exceptional, (2)
"This place was beautiful and in such a great location!"
Charming 3 bedrooms Apartment at the Medical District
Room in Town house Rogers Park
Living area
Room in Town house Rogers Park
Room in Town house Rogers Park
Wrigleyville Suites Room 3
Cozy bedroom with a grey patterned wallpaper wall, a queen sized bed with grey linens and white towels, two bedside tables with lamps, and a window with natural light.
Wrigleyville Suites Room 3
2.0 star property
The price is AED 528
AED 902 total
includes taxes & fees
10 Nov - 11 Nov
Wrigleyville Suites Room 3
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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Other property types in Westchester

Sentral Michigan Avenue
Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (583)
"Everything was great!"
The price is AED 459
AED 647 total
includes taxes & fees
12 Nov - 13 Nov
Sentral Michigan Avenue
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (201)
"Amazing and cant wait to stay here again!!"
The price is AED 256
AED 300 total
includes taxes & fees
3 Dec - 4 Dec
Sonder Market Hall
Sonder South Wabash
Living area
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (387)
"Clean and well located. We had access to the green and red line trains a few stops away from the loop. Entering the building was easy and convenient. Apartment was clean and spacious!! "
The price is AED 474
AED 556 total
includes taxes & fees
8 Dec - 9 Dec
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.

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 Millennium Park 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: The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the heart of Westchester.Old Chicago Inn: 10 rooms. 13.2 mi (21.3 km) from the downtown core. Enjoy the free full breakfast and fireplace in the lobby. 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 yard. Ray’s Bucktown B&B: 11 rooms. 11.3 mi (18.2 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. The Sono Chicago: 7 rooms. Located 13 mi (20.9 km) from the core of Westchester. Enjoy the rooftop terrace and fireplace in the lobby.
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 Millennium Park 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.