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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Winnetka

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.6 out of 10, Excellent, (51)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
The price is AED 356
AED 547 total
includes taxes & fees
15 Jul - 16 Jul
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (583)
"Was a great stay!"
The price is AED 271
AED 465 total
includes taxes & fees
16 Jul - 17 Jul
The Villa Toscana
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (474)
"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!"
The price is AED 528
AED 830 total
includes taxes & fees
21 Jul - 22 Jul
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (365)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is AED 817
AED 922 total
includes taxes & fees
20 Jul - 21 Jul
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (248)
"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!"
Wicker Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (463)
"Excellent location. Beautiful property, extremely clean."
The price is AED 767
AED 900 total
includes taxes & fees
23 Jul - 24 Jul
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (180)
"What a lovely place to stay. This bnb was perect!"
The price is AED 746
AED 842 total
includes taxes & fees
27 Jul - 28 Jul
The Publishing House B&B
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (111)
"Enjoyed my short stay. Wish I could have spent more time here! Quiet, peaceful, safe, and comfortable. I travel frequently for work and this is by far, one of the best experiences I have had. Thank you Beth!"
The price is AED 962
AED 1,102 total
includes taxes & fees
16 Jul - 17 Jul
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (103)
"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"
The price is AED 1,094
AED 1,284 total
includes taxes & fees
12 Aug - 13 Aug
Villa D' Citta
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, (139)
"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!
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...
The price is AED 406
AED 752 total
includes taxes & fees
16 Jul - 17 Jul
Wrigleyville Suites Room 1
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is AED 298
AED 623 total
includes taxes & fees
16 Jul - 17 Jul
Villa Dubois Guest House Room 4
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is AED 452
AED 808 total
includes taxes & fees
16 Jul - 17 Jul
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 406
AED 752 total
includes taxes & fees
16 Jul - 17 Jul
Wrigleyville Suites Room 3
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is AED 347
AED 682 total
includes taxes & fees
15 Jul - 16 Jul
Villa Dubois Guest House Room 1
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is AED 4,382
AED 6,582 total
includes taxes & fees
13 Aug - 14 Aug
Five bedroom - 3 bath - Sleeps 12
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

The price is AED 423
AED 773 total
includes taxes & fees
16 Jul - 17 Jul
Wrigleyville Suites Room 5
Wrigleyville Suites Room 6
Interior

Wrigleyville Suites Room 6

The price is AED 423
AED 773 total
includes taxes & fees
16 Jul - 17 Jul
Wrigleyville Suites Room 6
Wrigleyville Suites Room 4
Interior

Wrigleyville Suites Room 4

The price is AED 423
AED 773 total
includes taxes & fees
16 Jul - 17 Jul
Wrigleyville Suites Room 4
Presidential Suite
1 bedroom, iron/ironing board, WiFi, bed sheets

Presidential Suite

Presidential Suite
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

Searching for B&Bs in Winnetka?
If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your vacation. When you venture out to explore Winnetka, Lake Michigan is a some popular sight to visit.
How do you know if a B&B is the best choice for you?
With attentive service, opportunities to meet other guests, and hearty breakfasts, B&Bs all have a truly one-of-a-kind setting.
What are the best bed and breakfasts in Winnetka?
Here are some B&Bs in the surrounding area: The Villa Toscana: 9 rooms. 12.1 mi (19.5 km) from the heart of Winnetka.Dorothy's: 7 rooms. 12.1 mi (19.5 km) from the downtown core. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 9 mi (14.5 km) from the heart of Winnetka. Enjoy the designer toiletries and private yard. Ray's Bucktown B&B: 11 rooms. 13.2 mi (21.2 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. The Sono Chicago: 7 rooms. Located 14.6 mi (23.5 km) from the core of Winnetka. Enjoy the rooftop terrace and fireplace in the lobby.
When should I stay at a B&B in Winnetka?
When you're planning your escape to Winnetka, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Winnetka is 48 inches.
What is there to do in Winnetka?
When you want to spend some time in the great outdoors, Lake Michigan and Maple Street Beach are some notable spots. You might put Chocolate Box and Elder Lane Beach on your list if you want to see more of the area.
How can I get to and around Winnetka?
Mapping out your trip in and around Winnetka is easy with these transportation options. Fly into Chicago, IL (PWK-Chicago Executive), which is located 8.4 mi (13.5 km) away from the heart of the city. Otherwise, look for flights into Chicago O'Hare Intl. Airport (ORD), which is 12.5 mi (20.2 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.