A calm lake with ducks, autumn trees, and a grassy park area.

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Our top choices for Westchester bed & breakfast

A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

1. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (132 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is CA $319
CA $354 total
includes taxes & fees
Sep 7 - Sep 8
Harvey House Bed & Breakfast
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (548 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is CA $213
CA $250 total
includes taxes & fees
Sep 7 - Sep 8
The Sono Chicago
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

3. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (212 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is CA $326
CA $368 total
includes taxes & fees
Sep 7 - Sep 8
The Publishing House B&B
A bathroom with a glass-tiled wall, a sink, and a shower area.

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (413 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is CA $239
CA $270 total
includes taxes & fees
Sep 7 - Sep 8
Ray's Bucktown B&B
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

5. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (175 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is CA $84
CA $147 total
includes taxes & fees
Sep 9 - Sep 10
Dorothy's
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

6. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (669 reviews)
"Was a nice house the room we stayed in was cozy bed was really comfortable and in walking distance to wrigley field would definitely stay here again"
United States
John
The price is CA $95
CA $167 total
includes taxes & fees
Sep 7 - Sep 8
The Villa Toscana
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

7. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (517 reviews)
"I love the location of this B&B. Right across from a beautiful park, walkable to some fabulous restaurants and shops - and the red line is so close! My room was clean, quiet, cutely decorated. The kitchen was well-stocked with breakfast options. My one recommendation would be - I wish the coffee was higher quality! The host was prompt, friendly, and responsive to my needs. I'll be back for sure!"
United States
Kimberly
The price is CA $174
CA $290 total
includes taxes & fees
Sep 8 - Sep 9
House 5863 - Chicago Bed and Breakfast
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (281 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is CA $427
CA $501 total
includes taxes & fees
Sep 28 - Sep 29
Wicker Park Inn
A grand foyer with a wooden staircase, a chandelier, and a large window.

9. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (123 reviews)
"What a pleasant stay, staff was welcoming and wanting to make sure our needs were met with our expectations. Meals were abundant and homemade. Rooms w/bath were clean with abundant towels. We will stay again."
United States
Jeffrey
The price is CA $444
CA $521 total
includes taxes & fees
Sep 7 - Sep 8
Villa D' Citta
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $607
CA $712 total
includes taxes & fees
Sep 28 - Sep 29
Pristine Apartment with Free Street Parking
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Na"
Bylley 3-night trip
Posted 2 hours ago
Hilton Chicago

Find out more about Westchester

Westchester B&B information

Number of reviews
2,029
Accommodation
13 B&B
Lowest Price
CA $147
Highest Price
CA $712

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 Soldier Field 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 Sono Chicago: 7 rooms. 13 mi (20.9 km) from the heart of Westchester. Enjoy the rooftop terrace and fireplace in the lobby. Dorothy's: 7 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 Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the heart of downtown.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 Soldier Field 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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