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May 29 - May 31
Next weekend
Jun 5 - Jun 7

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Our top choices for Winnetka hotels

Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,511 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is ￥40,675
￥53,860 total
includes taxes & fees
Jun 14 - Jun 15
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (3,048 reviews)
"Great location nice room"
United States
Nolan
The price is ￥23,251
￥30,486 total
includes taxes & fees
Jun 29 - Jun 30
Freehand Chicago
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (1,513 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is ￥24,892
￥29,593 total
includes taxes & fees
Jun 22 - Jun 23
The Chicago Hotel Collection Ambassador Gold Coast
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,349 reviews)
"Beautiful Hotel great location"
United States
Nereida
The price is ￥29,155
￥34,664 total
includes taxes & fees
Jun 28 - Jun 29
Hilton Chicago/Magnificent Mile Suites
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (10,124 reviews)
"Excellent stay"
United States
Jennifer
The price is ￥20,735
￥24,651 total
includes taxes & fees
Jun 29 - Jun 30
Congress Plaza Hotel
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,243 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is ￥25,462
￥35,132 total
includes taxes & fees
Jun 28 - Jun 29
Silversmith Hotel Chicago Downtown
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (2,610 reviews)
"Staff was friendly and helpful.. location was great"
United States
Amber
The price is ￥21,355
￥25,390 total
includes taxes & fees
Jun 28 - Jun 29
Travelodge by Wyndham Downtown Chicago
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,486 reviews)
"Great stay"
United States
Ontario
The price is ￥24,205
￥28,777 total
includes taxes & fees
Jun 28 - Jun 29
The Chicago Hotel Collection - Magnificent Mile
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,287 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is ￥34,240
￥45,246 total
includes taxes & fees
Jun 29 - Jun 30
Hotel Riu Plaza Chicago
Exterior

Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,001 reviews)
"Room was clean great location"
United States
Eric
The price is ￥28,291
￥33,637 total
includes taxes & fees
Jun 28 - Jun 29
Hampton Inn Majestic Chicago Theatre District
2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,719 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
United States
Matson
The price is ￥35,600
￥46,998 total
includes taxes & fees
Jun 21 - Jun 22
LondonHouse Chicago, Curio Collection by Hilton
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,590 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is ￥35,672
￥42,411 total
includes taxes & fees
Jun 29 - Jun 30
Eurostars Magnificent Mile
Breakfast and dinner served

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,788 reviews)
"Great place at a great location."
United States
Alejandro
The price is ￥32,329
￥43,738 total
includes taxes & fees
Jun 14 - Jun 15
Omni Chicago Hotel
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,033 reviews)
"Clean room, friendly staff, nearby lots of stores and restaurants. "
United States
Nadiah
The price is ￥26,319
￥35,972 total
includes taxes & fees
Jun 28 - Jun 29
Warwick Allerton - Chicago
Exterior

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,003 reviews)
"The staff and up keep of the maintenance of the hotel was spectacular"
United States
Oziel Silva
The price is ￥25,321
￥34,840 total
includes taxes & fees
Jun 28 - Jun 29
Hotel Chicago Downtown, Autograph Collection by Marriott
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,832 reviews)
"great hotel and excellent to stay"
United States
Ruben
The price is ￥46,023
￥59,392 total
includes taxes & fees
Jun 8 - Jun 9
Hilton Chicago
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,251 reviews)
"Overall comfortable stay and easy access by walk to downtown and all other places in the city."
United States
raghu
The price is ￥30,449
￥36,202 total
includes taxes & fees
Jun 28 - Jun 29
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Shopping mall

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,970 reviews)
"Loved everything including location and food options. Great hotel. "
United States
Eileen
The price is ￥21,658
￥29,535 total
includes taxes & fees
Jun 28 - Jun 29
Millennium Hotel Knickerbocker Chicago
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,077 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is ￥35,688
￥47,151 total
includes taxes & fees
Jun 28 - Jun 29
Staypineapple, An Iconic Hotel, The Loop
Lobby lounge

Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (546 reviews)
"Nice hotel, well maintained, good breakfast, great location, spacious room."
United States
Niranjan
The price is ￥33,761
￥40,140 total
includes taxes & fees
Jun 28 - Jun 29
Residence Inn Chicago Downtown Magnificent 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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Stay near popular Winnetka attractions

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Learn more about Winnetka

Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theater.

See all hotels in Winnetka
Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Top Winnetka Hotel Reviews

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

8/10 Good
"Room was decent but outdated with wall paper lifting throughout the room and the hallways. Toro restaurant on site was good!"
sonia 3-night trip
Posted less than an hour ago
Fairmont Chicago at Millennium Park

More cheap stays in Winnetka

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

22 West Algonquin Road Arlington Heights IL
The price is ￥9,888 per night from Jun 12 to Jun 13
￥9,888
￥11,074 total
Jun 12 - Jun 13
includes taxes & fees
5.4/10 (1,003 reviews)

Frequently asked questions

What's the best place to stay in Winnetka?
Located 17.1 mi (27.5 km) from the heart of Winnetka, Congress Plaza Hotel is a top choice for your stay based on our traveler data. Two other options for your visit to the area are Hotel Riu Plaza Chicago and The Chicago Hotel Collection - Magnificent Mile. See all available top hotels, or vacation rentals in Winnetka.
What are some of the best vacation home rentals that Winnetka has to offer?
ENVITAE Hotel, 4BR Luxury Modern Apartments: Visitors like this Winnetka vacation home rental. It is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Winnetka.
If I need to cancel my hotel reservation in Winnetka, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winnetka.
Where can I learn more about changing or cancelling my trip to Winnetka?
For additional details about rescheduling or cancelling your trip to Winnetka, click here.
What's the best place to stay close to Elder Lane Beach?
DoubleTree by Hilton Chicago - North Shore Conference Center is one of the top choices for your stay based on our traveler data, and this 4-star hotel offers a restaurant and an outdoor pool. It's located 3.5 mi (5.6 km) from Elder Lane Beach. Other good options within 5 miles include Hampton Inn & Suites Chicago-North Shore/Skokie and Residence Inn by Marriott Chicago Wilmette/Skokie.
What's the best accommodation near O'Hare International Airport (ORD)?
Hilton Chicago O'Hare Airport is a popular 4-star hotel featuring 2 restaurants and 2 bars. It's located a short 0.1 mi (0.1 km) from O'Hare Intl. Airport. Other good options close to the airport are Edward Hotel Chicago and Best Western At O'Hare.
What is staying in Winnetka like?
Visitors can enjoy all that Winnetka has to offer including the shopping, forests, and sporting events. Tourists can also enjoy the city's restaurants and coffeehouses. Top sights around the area include Wrigley Field, Naval Base Great Lakes, and Navy Pier. In Winnetka, there are 2 hotels and other accommodations to choose from. Find out more about Winnetka.
What should I do while I'm visiting Winnetka?
Favorite places to visit include Lake Michigan, Chocolate Box, and Maple Street Beach. Additionally, you'll find Wrigley Field and Naval Base Great Lakes in the area. Check out what more to see and do in Expedia's Winnetka guide.
What's the best way to get around Winnetka?
To see more of the surrounding area, hop aboard a train at Winnetka Station or Winnetka Indian Hill Station. If you want to venture out around the area, you may want a rental car in Winnetka for your journey.
What's the seasonal weather like in Winnetka?
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.

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