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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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

Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2114)
"Fast and easy check in and check out! "
The price is AED 434
AED 509 total
includes taxes & fees
21 Apr - 22 Apr
Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North
Lobby

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very Good, (3859)
"Everyone was super friendly. My only issue was the wait to check in. They only had one employee working at check in time and the line was wrapped around the lobby."
The price is AED 468
AED 550 total
includes taxes & fees
21 Apr - 22 Apr
Embassy Suites by Hilton Chicago Downtown River North
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.8 out of 10, Excellent, (1007)
"Nice bar & restaurant. Nice lobby to relax in. I Greektown with numerous eateries, markets, drug store next door. #8 bus goes right up to Wrigley field. "
The price is AED 338
AED 397 total
includes taxes & fees
20 Apr - 21 Apr
Crowne Plaza Chicago West Loop by IHG
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4030)
"the hotel receptionist are pretty good "
The price is AED 384
AED 451 total
includes taxes & fees
22 Apr - 23 Apr
River Hotel
Swissotel - Chicago
Front of property - evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2038)
"Convenient location"
The price is AED 644
AED 863 total
includes taxes & fees
10 Apr - 11 Apr
Swissotel - Chicago
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2054)
"Great location. Staff were friendly and very accommodating. Very cute and clean rooms."
The price is AED 602
AED 707 total
includes taxes & fees
13 Apr - 14 Apr
L7 Chicago by LOTTE
The Allegro Royal Sonesta Hotel Chicago Loop
Exterior

The Allegro Royal Sonesta Hotel Chicago Loop

4.0 star property
8.8 out of 10, Excellent, (1627)
"My son and I stayed here for a weekend visit to Chicago. The staff were very friendly and overall it was a very nice property. The rooms are a bit small, but didn't feel overly cramped. Water pressure in the shower was amazing. Very convenient to the train and also overnight parking, which ended up being $50 less per day than the valet which was perfect since we didn't need our car at all."
The price is AED 526
AED 735 total
includes taxes & fees
20 Apr - 21 Apr
The Allegro Royal Sonesta Hotel Chicago Loop
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2894)
"Me and my husband enjoyed our stay. The view was beautiful, breakfast was great and the staff were welcoming. The only thing I didn’t like was the room was a bit small and didn’t have a bathtub but other than that our stay was pleasant!"
The price is AED 426
AED 501 total
includes taxes & fees
20 Apr - 21 Apr
citizenM Chicago Downtown
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8664)
"property, and staff met and exceeded all expectations. "
The price is AED 394
AED 463 total
includes taxes & fees
14 Apr - 15 Apr
Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (3191)
"Clean, good customer service, comfortable room."
The price is AED 380
AED 446 total
includes taxes & fees
20 Apr - 21 Apr
Hilton Garden Inn Chicago Downtown/Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1836)
"Very good stay. Everyone was friendly. Could not use a credit card all weekend.only cash and room charge. "
The price is AED 379
AED 445 total
includes taxes & fees
20 Apr - 21 Apr
DoubleTree by Hilton Chicago - Magnificent Mile
The Royal Sonesta Chicago River North
Terrace/patio

The Royal Sonesta Chicago River North

4.5 star property
9.0 out of 10, Wonderful, (1660)
"great location, AMAZING room (they upgraded me to a luxury spa suite, which was enormous with amenities including a jaccuzzi hot tub!), great little bar/restaurant on site, chic decor"
The price is AED 493
AED 696 total
includes taxes & fees
20 Apr - 21 Apr
The Royal Sonesta Chicago River North
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (1720)
"Everything from arranging parking, to checking in was convenient and easy. The whole place was very clean and had a very nice atmosphere. Will definitely be staying again next time I visit that part of Chicago."
The price is AED 311
AED 430 total
includes taxes & fees
13 Apr - 14 Apr
Freehand Chicago
Hotel Felix River North/Magnificent Mile
Lobby sitting area

Hotel Felix River North/Magnificent Mile

4.0 star property
8.0 out of 10, Very Good, (1566)
"Love it"
The price is AED 317
AED 468 total
includes taxes & fees
13 Apr - 14 Apr
Hotel Felix River North/Magnificent Mile
Hampton Inn & Suites Chicago Downtown
Lobby

Hampton Inn & Suites Chicago Downtown

3.0 star property
9.2 out of 10, Wonderful, (1185)
"Clean nice room. Staff friendly and helpful. Fabulous continental breakfast to start your day. "
The price is AED 387
AED 454 total
includes taxes & fees
13 Apr - 14 Apr
Hampton Inn & Suites Chicago Downtown
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (1692)
"Great customer service"
The price is AED 474
AED 660 total
includes taxes & fees
13 Apr - 14 Apr
Hotel Riu Plaza Chicago
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (1765)
"Only reason I did not give 5 stars is because property needs to be updated. "
The price is AED 643
AED 863 total
includes taxes & fees
20 Apr - 21 Apr
Hilton Chicago
The Royal Sonesta Chicago Downtown
Exterior

The Royal Sonesta Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2544)
"Prime Chicago location. Great views"
The price is AED 611
AED 835 total
includes taxes & fees
21 Apr - 22 Apr
The Royal Sonesta Chicago Downtown
Eurostars Magnificent Mile
Lobby lounge

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2949)
"Great"
The price is AED 470
AED 552 total
includes taxes & fees
20 Apr - 21 Apr
Eurostars Magnificent Mile
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2694)
"."
The price is AED 320
AED 375 total
includes taxes & fees
20 Apr - 21 Apr
Aloft Chicago Mag Mile
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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Other property types in Winnetka

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (723)
"Great family place to stay. "
The price is AED 403
AED 581 total
includes taxes & fees
13 Apr - 14 Apr
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (465)
"Great location to restaurants, grocery and easy to get to convention center or downtown"
The price is AED 403
AED 473 total
includes taxes & fees
16 Apr - 17 Apr
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (271)
"The property arranged an early check in for me when I arrived sick. They were super accommodating getting us into our room early. The apartment was very comfortable and had more than enough space for the three of us. Being just a block off the green and pink line trains also helped."
The price is AED 459
AED 538 total
includes taxes & fees
1 May - 2 May
Sonder Market Hall
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.

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. The Sono Chicago: 7 rooms. Situated 14.6 mi (23.5 km) from the heart of Winnetka. Enjoy the rooftop terrace and fireplace in the lobby. 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 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.