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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

Our top choices for Winnetka bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (489 reviews)
"Great location within easy walking distance to Old Town and public transit; comfortable room; welcoming staff; FREE Parking!"
United States
Andrea
The price is AED 422
AED 496 total
includes taxes & fees
11 Feb - 12 Feb
The Sono Chicago
Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (195 reviews)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is AED 663
AED 748 total
includes taxes & fees
8 Feb - 9 Feb
The Publishing House B&B
Living area

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very Good, (104 reviews)
"cozy and close to cool places"
United States
Winter Fox
The price is AED 129
AED 279 total
includes taxes & fees
25 Jan - 26 Jan
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (628 reviews)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is AED 117
AED 284 total
includes taxes & fees
29 Jan - 30 Jan
The Villa Toscana
Courtyard

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497 reviews)
"Nice shared spaces"
United States
Erica
The price is AED 363
AED 645 total
includes taxes & fees
25 Jan - 26 Jan
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, (259 reviews)
"Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so."
United States
Jeffrey
Wicker Park Inn
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (113 reviews)
"Great place"
United States
Jeffrey
The price is AED 756
AED 888 total
includes taxes & fees
26 Jan - 27 Jan
Villa D' Citta
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (386 reviews)
"We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!"
United States
Kristin
The price is AED 639
AED 721 total
includes taxes & fees
15 Feb - 16 Feb
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, (122 reviews)
"Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park "
United States
Elizabeth
The price is AED 848
AED 942 total
includes taxes & fees
26 Jan - 27 Jan
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Incredible location and wonderful satff"
Michael 1-night trip
Posted 13 hours ago
Hotel Riu Plaza Chicago

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: Dorothy's: 7 rooms. 12.1 mi (19.5 km) from the heart of Winnetka.The Villa Toscana: 9 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. The Publishing House B&B: 11 rooms. 16.1 mi (25.9 km) from the heart of downtown. Enjoy the free full breakfast and winery. 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.