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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

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

Dorothy's
Full-size fridge, microwave, toaster oven, cookware/dishes/utensils

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (46)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
$142 nightly
The price is $161
Jun 30 - Jul 1
Total includes taxes and fees
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (571)
"Was a great stay!"
$158 nightly
The price is $179
Jun 27 - Jun 28
Total includes taxes and fees
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (360)
"Breakfast was great, the staff was kind, and it was a pleasant surprise. "
$190 nightly
The price is $215
Jun 25 - Jun 26
Total includes taxes and fees
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (462)
"Excellent location. Beautiful property, extremely clean."
$155 nightly
The price is $182
Jun 30 - Jul 1
Total includes taxes and fees
The Sono Chicago
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (473)
"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!"
$131 nightly
The price is $154
Jul 16 - Jul 17
Total includes taxes and fees
House 5863 - Chicago Bed and Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (177)
"Incredible service, amazing breakfast and gorgeous rooms."
$216 nightly
The price is $244
Jul 20 - Jul 21
Total includes taxes and fees
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (247)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
$262 nightly
The price is $307
Jun 25 - Jun 26
Total includes taxes and fees
Wicker Park Inn
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
$262 nightly
The price is $300
Jul 7 - Jul 8
Total includes taxes and fees
Harvey House Bed & Breakfast
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (137)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (101)
"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"
$263 nightly
The price is $309
Jul 8 - Jul 9
Total includes taxes and fees
Villa D' Citta
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...
$275 nightly
The price is $317
Jun 27 - Jun 28
Total includes taxes and fees
Wrigleyville Suites Room 1
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

$248 nightly
The price is $285
Jun 26 - Jun 27
Total includes taxes and fees
Villa Dubois Guest House Room 4
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

$209 nightly
The price is $239
Jun 29 - Jun 30
Total includes taxes and fees
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

$165 nightly
The price is $186
Jun 25 - Jun 26
Total includes taxes and fees
Villa Dubois Guest House Room 2
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

$165 nightly
The price is $186
Jun 25 - Jun 26
Total includes taxes and fees
Villa Dubois Guest House Room 5
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
$275 nightly
The price is $317
Jun 27 - Jun 28
Total includes taxes and fees
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)
Wrigleyville Suites Room 2
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

$178 nightly
The price is $202
Jun 25 - Jun 26
Total includes taxes and fees
Villa Dubois Guest House Room 1
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

$1,016 nightly
The price is $1,155
Jun 30 - Jul 1
Total includes taxes and fees
Five bedroom - 3 bath - Sleeps 12
Wrigleyville Suites Room 6
Interior

Wrigleyville Suites Room 6

$284 nightly
The price is $328
Jun 27 - Jun 28
Total includes taxes and fees
Wrigleyville Suites Room 6
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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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 $154 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.