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Check prices for these dates

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Jul 3 - Jul 5
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Our top choices for Westchester bed & breakfast

Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (208 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is CA $387
CA $437 total
includes taxes & fees
Jul 19 - Jul 20
The Publishing House B&B
Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (526 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is CA $217
CA $254 total
includes taxes & fees
Jul 6 - Jul 7
The Sono Chicago
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (140 reviews)
"lots of clean rooms and clean bathrooms with products you can use. keep in mind however that not every room has its own private bathroom "
United States
Jia
The price is CA $101
CA $169 total
includes taxes & fees
Jul 13 - Jul 14
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (651 reviews)
"Small, but very convenient! Excellent location!"
Canada
Jeremy
The price is CA $139
CA $219 total
includes taxes & fees
Jul 13 - Jul 14
The Villa Toscana
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (402 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is CA $293
CA $331 total
includes taxes & fees
Jun 29 - Jun 30
Ray's Bucktown B&B
Presidential Studio Suite, 2 Bedrooms (1st Floor) | Living area

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (507 reviews)
"The place is well run. The communal areas are clean and have what you need. The neighborhood is nice, everyone i took was gorgeous! And the perfect distance from the city."
United States
Joanna
The price is CA $186
CA $306 total
includes taxes & fees
Jul 8 - Jul 9
House 5863 - Chicago Bed and Breakfast
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (269 reviews)
"Very nice place and great location with a lot of restaurants and shops."
United States
Regina
The price is CA $325
CA $381 total
includes taxes & fees
Jul 6 - Jul 7
Wicker Park Inn
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (128 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
The price is CA $384
CA $426 total
includes taxes & fees
Jul 6 - Jul 7
Harvey House Bed & Breakfast
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (121 reviews)
"A fantastic stay yet again. I have stayed here the last few years while attending a conference. All the staff were great and amazing selection of food for breakfast and for late night snacks. I will be back again next year"
United Kingdom
Robert
The price is CA $405
CA $476 total
includes taxes & fees
Jul 5 - Jul 6
Villa D' Citta
Fridge, microwave, oven, coffee/tea maker

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $569
CA $670 total
includes taxes & fees
Jun 30 - Jul 1
Pristine Apartment with Free Street Parking
TV

Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
The price is CA $1,087
CA $2,114 total
includes taxes & fees
Jul 13 - Jul 14
Five bedroom - 3 bath - Sleeps 12
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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Top Westchester Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"excellent location. Majority of the room is renovated but some part are still look worn"
Kevin 4-night trip
Posted less than an hour ago
Congress Plaza Hotel

Find out more about Westchester

Westchester B&B information

Number of reviews
2,952
Accommodation
13 B&B
Lowest Price
CA $169
Highest Price
CA $670

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 Sono Chicago: 7 rooms. 13 mi (20.9 km) from the downtown core. Enjoy the rooftop terrace 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. The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the heart of downtown.Ray's Bucktown B&B: 11 rooms. Located 11.3 mi (18.2 km) from the core of Westchester. Enjoy the free cooked breakfast and rooftop terrace.
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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