Westchester B&B: Find the Best Bed and Breakfast from CA $108

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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

Oak Park

Monica

CA $400 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

2. Dorothy's

Lakeview

Ginny

CA $108 total

includes taxes & fees

Nov 24 - Nov 25

A narrow stone pathway leading to a house with a green porch and a large tree overhanging the path.

3. The Villa Toscana

Lakeview

John

CA $151 total

includes taxes & fees

Nov 3 - Nov 4

A patio with a grill, outdoor seating, and potted plants.

4. Ray's Bucktown B&B

Bucktown

Lora

CA $308 total

includes taxes & fees

Nov 3 - Nov 4

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

5. The Sono Chicago

Near North Side

Tavarion

CA $266 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

6. House 5863 - Chicago Bed and Breakfast

Edgewater

Malena

CA $280 total

includes taxes & fees

Nov 8 - Nov 9

A brick building with a sign for The Wicker Park Inn, including a phone number and website.

7. Wicker Park Inn

West Town

Mary

CA $398 total

includes taxes & fees

Nov 16 - Nov 17

A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

8. The Publishing House B&B

Downtown Chicago

Nobue

CA $463 total

includes taxes & fees

Nov 8 - Nov 9

A grand foyer with a wooden staircase, a chandelier, and a large window.

9. Villa D' Citta

Lincoln Park

Hernando

CA $338 total

includes taxes & fees

Dec 2 - Dec 3

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Humboldt Park

CA $374 total

includes taxes & fees

Nov 30 - Dec 1

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Top Westchester Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"The staff at the concierge were very knowledgeable and helpful day 1 until 4, On my second night, oct 29th, except for the lady staff who was in the lobby bar, she was not accommodating and just giving us a negative answer when we are asking if there if coffee is included in the drinks voucher, she did not even us told us that there was Keurig coffee maker an the right side corner, she is the only one that"

L7 Chicago by LOTTE

10/10 Excellent

"Best hotel sleep in years, which is wild given the central location in a busy city. In-room amenities like the steamer, robe, kettle and yoga mat really elevated my stay. No onsite food except that expensive restaurant downstairs, but there’s an amazing pub literally across the street that’s huge, reasonable and open late. Free coffee in lobby was nice too. Only drawback was the lack of a desk chair in the room. There was a lounger and a table but trying to work from it for more than a few hours was a little rough in my back. I’d definitely stay again."

Arlo Chicago

10/10 Excellent

"Arlo Chicago was perfect! If you are in a wheelchair, the ADA King room was fully accessible with a low sitting bed, walk-in shower, open sinks, and enough space to get around room. It was quiet with electric blinds making it easy to open/close. The location is within walking distance of just about anything, or a bus stop and train station right out front or a block down to access train. The famous Bean site was a 2 minute walk, the Riverwalk about 5 minutes, and so much more. The parking was so easy. You pull right at back door & unload, and the parking garage is literally at the end of that alley. That was my biggest concern being my first overnight stay in a wheelchair where I must transfer in/out my chair. There is a bar and restaurant inside the hotel, drinks (for a fee) already in the room, a refrigerator, alcohol, water, soda, coffee machine, toiletries, robes, etc. The view was awesome. Thank you for the amazing staff who were so kind & helpful...especially Terell who was more than accommodating in helping us register with parking garage online. The room was clean, common areas welcoming, and I will only stay at this location in the future. My only criticism is that the ADA room had a heavy door and was a sharp right angle to enter, which could potentially be an issue for an electric wheelchair user if they were traveling alone...but the staff would have helped. Be prepared financially, but our room was worth the rate & reasonable for all the amenities."

Find out more about Westchester

Westchester B&B information

Number of reviews	1,182
Accommodation	12 B&B
Lowest Price	CA $108
Highest Price	CA $463

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. The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the downtown core. Dorothy's: 7 rooms. Situated 13.6 mi (21.9 km) from the heart of Westchester. House 5863 - Chicago Bed and Breakfast: 7 rooms. 14.7 mi (23.6 km) from the heart of downtown. Enjoy the designer toiletries and private yard. 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 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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Things to do in Chicago

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Westchester bed & breakfast

1. Harvey House Bed & Breakfast

2. Dorothy's

3. The Villa Toscana

4. Ray's Bucktown B&B

5. The Sono Chicago

6. House 5863 - Chicago Bed and Breakfast

7. Wicker Park Inn

8. The Publishing House B&B

9. Villa D' Citta

10. Pristine Apartment with Free Street Parking

Top Westchester Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

L7 Chicago by LOTTE

Arlo Chicago

The Wade

Congress Plaza Hotel

Fairmont Chicago at Millennium Park

Hotel Saint Clair- Magnificent Mile

Find out more about Westchester

Westchester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Westchester from CA $108

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Westchester bed & breakfast

1. Harvey House Bed & Breakfast

2. Dorothy's

3. The Villa Toscana

4. Ray's Bucktown B&B

5. The Sono Chicago

6. House 5863 - Chicago Bed and Breakfast

7. Wicker Park Inn

8. The Publishing House B&B

9. Villa D' Citta

10. Pristine Apartment with Free Street Parking

Top Westchester Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

Find out more about Westchester

Westchester B&B information

Frequently asked questions

Explore a world of travel with Expedia