A suburban street with a stone house, a tree, and a clear sky.

Book Winnetka Bed & Breakfast

Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Winnetka bed & breakfast

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

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (173 reviews)
"Great location, just what we needed."
United States
Stephanie
$121 nightly
The price is $135
Sep 9 - Sep 10
Total with taxes and fees
Dorothy's
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, (545 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
$142 nightly
The price is $167
Aug 31 - Sep 1
Total with taxes and fees
The Sono Chicago
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

3. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (515 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
$179 nightly
The price is $210
Aug 31 - Sep 1
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

4. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (211 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
$230 nightly
The price is $260
Aug 31 - Sep 1
Total with taxes and fees
The Publishing House B&B
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

5. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very Good, (668 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
$147 nightly
The price is $166
Sep 2 - Sep 3
Total with taxes and fees
The Villa Toscana
A bathroom with a glass-tiled wall, a sink, and a shower area.

6. 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
$184 nightly
The price is $207
Aug 31 - Sep 1
Total with taxes and fees
Ray's Bucktown B&B
A grand foyer with a wooden staircase, a chandelier, and a large window.

7. 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
$286 nightly
The price is $336
Sep 2 - Sep 3
Total with taxes and fees
Villa D' Citta
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
$318 nightly
The price is $374
Sep 1 - Sep 2
Total with taxes and fees
Wicker Park Inn
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

9. 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
$271 nightly
The price is $301
Aug 31 - Sep 1
Total with taxes and fees
Harvey House Bed & Breakfast
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
$543 nightly
The price is $559
Sep 9 - Sep 10
Total with taxes and fees
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 Winnetka Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"This was a clean stay! The staff members were pleasant. The location of the hotel was next to a lot of great tourist spots. The building is an older building but extremely clean and convenient. A big perk was that the Hop On Hop off bus was right outside the front door. I would stay at this location again."
Whitney 3-night trip
Posted 1 hour ago
Hilton Chicago

Find out more about Winnetka

Winnetka B&B information

Number of reviews
1,526
Accommodation
13 B&B
Lowest Price
$135
Highest Price
$559

Frequently asked questions

What is the nightly rate for a B&B in Winnetka?
Prices for B&Bs in Winnetka often vary, but you can find a great deal from $135 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winnetka B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Winnetka?
The best time to book a B&B in Winnetka is during the late spring and summer months, particularly from May to August. This vibrant period welcomes families and travelers seeking a charming coastal escape, with plenty of opportunities for leisurely beach days and outdoor activities. The warm temperatures, typically ranging from the mid-60s to the high 80s Fahrenheit, create an inclusive setting for exploring the picturesque waterfront and enjoying local festivals.

July stands out as the most popular month to visit Winnetka, as residents and visitors alike take advantage of the sun-soaked days and festive community events. During this time, you can indulge in delightful strolls along the beach, savor local cuisine at outdoor eateries, and partake in various cultural activities that reflect the area's lively spirit.

If you're looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, allowing for peaceful walks along the beach and the chance to enjoy the stunning fall foliage in the surrounding parks. It's also a lovely time for exploring local shops and cafes without the summer crowds.
What is the difference between a Winnetka Bed and Breakfast and a hotel?
Every Winnetka B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winnetka B&Bs.

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