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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Winnetka

Private kitchen
The Sono Chicago

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (483)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
The price is SAR 491
SAR 576 total
includes taxes & fees
8 Dec - 9 Dec
The Sono Chicago
Lobby sitting area
Villa D' Citta

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (111)
"Great place"
United States
Jeffrey
The price is SAR 773
SAR 907 total
includes taxes & fees
3 Dec - 4 Dec
Villa D' Citta
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12

Lakeview
The price is SAR 1,576
SAR 2,901 total
includes taxes & fees
17 Dec - 18 Dec
Five bedroom - 3 bath - Sleeps 12
Free WiFi, bed sheets
Dorothy's

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very Good, (97)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
The price is SAR 92
SAR 239 total
includes taxes & fees
3 Dec - 4 Dec
Dorothy's
Exterior
The Villa Toscana

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (623)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is SAR 78
SAR 241 total
includes taxes & fees
3 Dec - 4 Dec
The Villa Toscana
Staircase
The Publishing House B&B

The Publishing House B&B

3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (188)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is SAR 682
SAR 770 total
includes taxes & fees
18 Dec - 19 Dec
The Publishing House B&B
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (492)
"Easy check-in, c. Easy parking. "
United States
Jordan
The price is SAR 410
SAR 686 total
includes taxes & fees
14 Dec - 15 Dec
House 5863 - Chicago Bed and Breakfast
Property entrance
Wicker Park Inn

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 star property
Bucktown
9.8 out of 10, Exceptional, (382)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is SAR 592
SAR 668 total
includes taxes & fees
3 Dec - 4 Dec
Ray's Bucktown B&B
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (119)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
United States
Bethany
The price is SAR 867
SAR 962 total
includes taxes & fees
1 Jan - 2 January 2026
Harvey House Bed & Breakfast
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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Loved our room! Small, but cozy and high tech. No issues at all. Staff was great! Helpful and friendly. "
Dave 3-night trip
Posted 3 hours ago
citizenM Chicago Downtown

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 Sono Chicago: 7 rooms. 14.6 mi (23.5 km) from the heart of Winnetka. Enjoy the rooftop terrace and fireplace in the lobby. Dorothy's: 7 rooms. 12.1 mi (19.5 km) from the downtown core. The Villa Toscana: 9 rooms. Situated 12.1 mi (19.5 km) from the heart of Winnetka. 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. House 5863 - Chicago Bed and Breakfast: 7 rooms. Located 9 mi (14.5 km) from the core of Winnetka. Enjoy the designer toiletries and private yard.
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.