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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 28 B&B in Westchester with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (548)
"Super cute house! Very detailed directions on check in, super easy excellent neighbourhood!"
The price is SAR 135
SAR 309 total
includes taxes & fees
30 Apr - 1 May
The Villa Toscana
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (170)
"Was surprisingly excellent "
The price is SAR 875
SAR 988 total
includes taxes & fees
26 May - 27 May
The Publishing House B&B
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (347)
"What a rad spot...great staff, A M A Z I N G breakfast (can I say Nutella and banana stuffed French toast?!), nice sauna on premise, clean rooms, so much to look at, and I parked in the garage! Will be back...daughters had a blast. "
The price is SAR 539
SAR 609 total
includes taxes & fees
30 Apr - 1 May
Ray's Bucktown B&B
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.0 out of 10, Very Good, (30)
"It was great for a stay in Boystown"
The price is SAR 152
SAR 310 total
includes taxes & fees
30 Apr - 1 May
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (452)
"This bed and breakfast was an absolutely breathtaking gem that surpassed every expectation we had, delivering an experience that went well beyond what the photographs could capture. From the moment we arrived, we were struck by the stunning beauty of the place, which seemed to offer everything one could possibly desire in a cozy getaway. The owners were the epitome of hospitality—warm, welcoming, and genuinely sweet—always ready to lend a hand with anything we needed, whether it was local...
The price is SAR 549
SAR 645 total
includes taxes & fees
11 May - 12 May
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is SAR 896
SAR 1,052 total
includes taxes & fees
30 Apr - 1 May
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is SAR 772
SAR 907 total
includes taxes & fees
29 Apr - 30 Apr
Villa D' Citta
Harvey House Bed & Breakfast
Free daily breakfast

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is SAR 867
SAR 962 total
includes taxes & fees
29 Apr - 30 Apr
Harvey House Bed & Breakfast
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...
The price is SAR 539
SAR 935 total
includes taxes & fees
29 Apr - 30 Apr
Wrigleyville Suites Room 1
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is SAR 726
SAR 1,079 total
includes taxes & fees
29 Apr - 30 Apr
House 5863 - Chicago Bed and Breakfast
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 1,069 total
includes taxes & fees
1 May - 2 May
Dubois Guest House Room 201
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is SAR 506
SAR 892 total
includes taxes & fees
1 May - 2 May
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is SAR 334
SAR 672 total
includes taxes & fees
30 Apr - 1 May
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is SAR 284
SAR 612 total
includes taxes & fees
29 Apr - 30 Apr
Dubois Guest House Room 101
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is SAR 633
SAR 1,069 total
includes taxes & fees
1 May - 2 May
Dubois Guest House Room 202
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is SAR 349
SAR 691 total
includes taxes & fees
29 Apr - 30 Apr
Villa Dubois Guest House Room 4
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is SAR 349
SAR 691 total
includes taxes & fees
29 Apr - 30 Apr
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is SAR 760
SAR 1,241 total
includes taxes & fees
1 May - 2 May
Dubois Guest House Room 203
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is SAR 539
SAR 935 total
includes taxes & fees
29 Apr - 30 Apr
Wrigleyville Suites Room 3
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is SAR 539
SAR 935 total
includes taxes & fees
29 Apr - 30 Apr
Wrigleyville Suites Room 2
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
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (737)
"Wonderful stay, beautiful views, spacious and clean!"
The price is SAR 507
SAR 705 total
includes taxes & fees
30 Apr - 1 May
Sentral Michigan Avenue
Sonder South Wabash
36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (484)
"Good place"
The price is SAR 440
SAR 517 total
includes taxes & fees
26 May - 27 May
Sonder South Wabash
Sonder Market Hall
City view from property

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (274)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is SAR 489
SAR 574 total
includes taxes & fees
26 May - 27 May
Sonder Market Hall
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 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: The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the heart of Westchester.Dorothy’s: 7 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. Wicker Park Inn: 11 rooms. 11.4 mi (18.3 km) from the heart of downtown.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 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.