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Check prices for these dates

Next weekend
19 Sep - 21 Sep
In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

B&B in Westchester

Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (72)
"Clean room beautiful.yards convenient"
The price is SAR 300
SAR 484 total
includes taxes & fees
29 Sep - 30 Sep
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (597)
"Was a great stay!"
The price is SAR 344
SAR 554 total
includes taxes & fees
6 Oct - 7 Oct
The Villa Toscana
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (182)
"What a lovely place to stay. This bnb was perect!"
The price is SAR 790
SAR 892 total
includes taxes & fees
5 Oct - 6 Oct
The Publishing House 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, (480)
"Everything was taken care of! A wonderful stay. "
The price is SAR 427
SAR 708 total
includes taxes & fees
14 Sep - 15 Sep
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (373)
"Absolutely one of the best stays I’ve ever had. "
The price is SAR 652
SAR 736 total
includes taxes & fees
16 Sep - 17 Sep
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (252)
"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
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (473)
"Loved the shared kitchen access! "
The price is SAR 801
SAR 941 total
includes taxes & fees
22 Sep - 23 Sep
The Sono Chicago
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (106)
"Would stay again anytime!!"
The price is SAR 988
SAR 1,160 total
includes taxes & fees
15 Sep - 16 Sep
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is SAR 983
SAR 1,091 total
includes taxes & fees
15 Sep - 16 Sep
Harvey House Bed & Breakfast
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is SAR 506
SAR 888 total
includes taxes & fees
17 Sep - 18 Sep
Villa Dubois Guest Room 6
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (147)
"The location was fantastic, the apartment was perfect, and the wine bar below was delicious - our only regret is that we didn’t visit the wine bar more often. "
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
Wrigleyville Suites Room 3
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

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...
Wrigleyville Suites Room 1
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is SAR 633
SAR 1,095 total
includes taxes & fees
16 Sep - 17 Sep
Dubois Guest House Room 101
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is SAR 506
SAR 888 total
includes taxes & fees
16 Sep - 17 Sep
Villa Dubois Guest House Room 5
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is SAR 633
SAR 1,095 total
includes taxes & fees
12 Sep - 13 Sep
Dubois Guest House Room 201
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is SAR 633
SAR 1,082 total
includes taxes & fees
16 Sep - 17 Sep
Villa Dubois Guest House Room 2
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is SAR 633
SAR 1,095 total
includes taxes & fees
14 Sep - 15 Sep
Villa Dubois Guest House Room 4
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
The price is SAR 633
SAR 1,095 total
includes taxes & fees
12 Sep - 13 Sep
Dubois Guest House Room 202
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

Wrigleyville Suites Room 5
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"Loved the location and the staff was friendly. "
Peter 1-night trip
Posted 3 hours ago
Hotel Felix River North/Magnificent Mile

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. 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 Sono Chicago: 7 rooms. 13 mi (20.9 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. 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.