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

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8

Our top choices for Winnetka bed & breakfast

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

1. 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
$179 nightly
The price is $210
Sep 23 - Sep 24
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

2. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (176 reviews)
"Great location, just what we needed."
United States
Stephanie
$147 nightly
The price is $166
Oct 12 - Oct 13
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.

3. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (550 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
$212 nightly
The price is $249
Sep 13 - Sep 14
Total with taxes and fees
The Sono Chicago
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

4. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very Good, (674 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
$154 nightly
The price is $174
Oct 5 - Oct 6
Total with taxes and fees
The Villa Toscana
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

5. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (213 reviews)
"This was such a perfect place to stay and I'll definitely stay here whenever going to Chicago. It was close enough to downtown to make it easy to access, but far enough away to be out of the hustle and bustle. The staff were all friendly and kind, the room was beautiful, the bed was very comfy, and the whole place had such a fun vibe and great decor. Breakfast was tasty and the menu options felt like something you'd order at your favorite fancy brunch spot, with fruit and pastries to round it...
United States
Julie
$288 nightly
The price is $325
Sep 27 - Sep 28
Total with taxes and fees
The Publishing House B&B
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, (414 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
$190 nightly
The price is $215
Sep 27 - Sep 28
Total with taxes and fees
Ray's Bucktown B&B
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

7. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (134 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
$293 nightly
The price is $325
Sep 21 - Sep 22
Total with taxes and fees
Harvey House Bed & Breakfast
A grand foyer with a wooden staircase, a chandelier, and a large window.

8. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (125 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
$252 nightly
The price is $296
Oct 5 - Oct 6
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.

9. 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
$343 nightly
The price is $402
Sep 29 - Sep 30
Total with taxes and fees
Wicker Park Inn
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
$487 nightly
The price is $499
Sep 28 - Sep 29
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Great"
Hiba 3-night trip
Posted less than an hour ago
Fairmont Chicago at Millennium Park

Find out more about Winnetka

Winnetka B&B information

Number of reviews
1,747
Accommodation
13 B&B
Lowest Price
$166
Highest Price
$499

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 $166 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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