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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 24 B&B in Winnetka with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (557)
"Super easy to find parking, quick walk to cubs game and bars after. Safe neighborhood and the greatest pizza place right through the gate. It was awesome!"
The price is AED 426
AED 647 total
includes taxes & fees
5 Jun - 6 Jun
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (38)
"I initially came up to Chicago from Indiana and had found this place to stay for my duration. The area was lovely, arrangements were excellent and I loved the cottage feel to the Bed N’ Breakfast next door. If I’m ever in Chicago for another concert or to see more of the place, I’m coming back to Dorothy’s."
The price is AED 447
AED 653 total
includes taxes & fees
16 Jun - 17 Jun
Dorothy's
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (355)
"Breakfast was great, the staff was kind, and it was a pleasant surprise. "
The price is AED 698
AED 788 total
includes taxes & fees
3 Jun - 4 Jun
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (455)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 767
AED 900 total
includes taxes & fees
4 Jun - 5 Jun
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (176)
"Incredible service, amazing breakfast and gorgeous rooms."
The price is AED 885
AED 999 total
includes taxes & fees
22 Jun - 23 Jun
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is AED 1,094
AED 1,284 total
includes taxes & fees
10 Jun - 11 Jun
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (100)
"What a wonderful and unique place where everything is so beautifully decorated with the owners personalized touch. The kitchen and amenities are exceptional and the best part was breakfast and visiting with Gina. Will be our only go-to now in Chicago."
The price is AED 1,094
AED 1,284 total
includes taxes & fees
2 Jun - 3 Jun
Villa D' Citta
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."
The price is AED 962
AED 1,068 total
includes taxes & fees
29 May - 30 May
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, (135)
"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 494
AED 871 total
includes taxes & fees
29 May - 30 May
Wrigleyville Suites Room 1
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!"
The price is AED 590
AED 907 total
includes taxes & fees
3 Jun - 4 Jun
House 5863 - Chicago Bed and Breakfast
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 496
AED 885 total
includes taxes & fees
4 Jun - 5 Jun
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is AED 496
AED 885 total
includes taxes & fees
16 Jun - 17 Jun
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is AED 620
AED 1,058 total
includes taxes & fees
3 Jun - 4 Jun
Villa Dubois Guest House Room 2
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 520
AED 905 total
includes taxes & fees
29 May - 30 May
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 494
AED 871 total
includes taxes & fees
29 May - 30 May
Wrigleyville Suites Room 3
Five bedroom - 3 bath - Sleeps 12
Free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is AED 3,285
AED 5,122 total
includes taxes & fees
8 Jun - 9 Jun
Five bedroom - 3 bath - Sleeps 12
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is AED 372
AED 712 total
includes taxes & fees
29 May - 30 May
Villa Dubois Guest House Room 1
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

Wrigleyville Suites Room 5
Wrigleyville Suites Room 6
Interior

Wrigleyville Suites Room 6

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

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. Ray’s Bucktown B&B: 11 rooms. Situated 13.2 mi (21.2 km) from the heart of Winnetka. Enjoy the free cooked breakfast and rooftop terrace. The Sono Chicago: 7 rooms. 14.6 mi (23.5 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. The Publishing House B&B: 11 rooms. Located 16.1 mi (25.9 km) from the core of Winnetka. Enjoy the free full breakfast and winery.
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.