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8 Dec - 9 Dec
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Top hotels and accommodation in Winnetka

Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2954)
"Great location and great staff!!"
United States
lynne
The price is AU$148
includes taxes & fees
11 Dec - 12 Dec
Aloft Chicago Mag Mile
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2181)
"Nice Hotel"
United States
Alan
The price is AU$158
includes taxes & fees
16 Dec - 17 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2747)
"Great food clean room friendly staff"
United States
MARINA
The price is AU$191
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4850)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is AU$144
includes taxes & fees
21 Dec - 22 Dec
River Hotel
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3441)
"Great hotel"
United States
Clara
The price is AU$205
includes taxes & fees
21 Dec - 22 Dec
voco Chicago Downtown - Riverwalk by IHG
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3446)
"Great place to stay "
United States
RaShawna
The price is AU$186
includes taxes & fees
14 Dec - 15 Dec
Hilton Chicago/Magnificent Mile Suites
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2113)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3391)
"Everything was amazing, from the staff to the room, amenities simply perfect.!! "
United States
TERESA
The price is AU$285
includes taxes & fees
22 Dec - 23 Dec
Hyatt Regency Chicago
Lobby
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3429)
"Great Hotel!"
United States
Siranush
The price is AU$231
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3149)
"Amazing and will be staying again!"
United States
Angie
The price is AU$165
includes taxes & fees
6 Jan - 7 Jan 2026
Eurostars Magnificent Mile
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (4231)
"Staff were amazing."
United States
Debra
The price is AU$145
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3006)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is AU$164
includes taxes & fees
5 Jan - 6 Jan 2026
Warwick Allerton - Chicago
Snack bar
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1455)
"Clean, modern, friendly/helpful staff, the perfect spot for staying for a show at The Chicago Theatre. Parking was close and easy too. "
United States
Megan
The price is AU$160
includes taxes & fees
4 Jan - 5 Jan 2026
Cambria Hotel Chicago Loop - Theatre District
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1956)
"A good place for stay "
United States
Julio
The price is AU$147
includes taxes & fees
11 Dec - 12 Dec
Club Quarters Hotel Wacker at Michigan, Chicago
American cuisine, al fresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1914)
"Awesome staff and great location "
United States
Luis C
The price is AU$190
includes taxes & fees
29 Dec - 30 Dec
The Godfrey Hotel Chicago
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2120)
"Loved and enjoyed our stay"
United States
Luis
The price is AU$219
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Terrace/patio
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2306)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is AU$230
includes taxes & fees
5 Jan - 6 Jan 2026
The Royal Sonesta Chicago River North
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 star property
Downtown Chicago
8.2 out of 10, Very good, (3795)
"Spacious room, cute boutique hotel in great location!"
United States
Julie
The price is AU$135
includes taxes & fees
9 Dec - 10 Dec
The Whitehall Hotel, BW Premier Collection
Exterior
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2032)
"Great hotel."
United States
Mario
The price is AU$173
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Chicago Dwtn - The Mart by IHG
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2999)
"Very beautiful place to stay"
United States
FaithBrenda
The price is AU$246
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
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

Elder Lane Beach

Why not spend a lazy afternoon at Elder Lane Beach during your trip to Winnetka? Amble around the area's forests or visit its shops.
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 theatre.

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

Recent Reviews in Winnetka

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent
"Wonderful staff. Very friendly and knowledgeable about local events and recommendations for entertainment. Property was clean at all times and walkable even during inclement weather conditions. I would definitely return."
Jeneen 1-night trip
Posted 9 hours ago
Sable at Navy Pier Chicago, Curio Collection by Hilton

More cheap accommodation in Winnetka

Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

4021 North Mannheim Rd Schiller Park IL
The price is AU$139 per night from 9 Dec to 10 Dec
AU$139
9 Dec - 10 Dec
includes taxes & fees
8.2/10 Very Good! (2,165 reviews)

Frequently asked questions

What's the best place to stay in Winnetka?
Located 16.7 mi (26.8 km) from the heart of Winnetka, Palmer House a Hilton Hotel is a top choice for your stay, based on our traveller data. Other good choices for your trip to the area are Embassy Suites by Hilton Chicago Downtown River North and Hilton Chicago/Magnificent Mile Suites. See all available top hotels, or vacation rentals in Winnetka.
What are some of the best holiday rentals that Winnetka has to offer?
NEW to the market! Relax with family in a super Lux Custom SFH. West town.: This holiday home rental outside of Winnetka offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden. See all vacation rentals in Winnetka.
If I need to cancel my hotel reservation in Winnetka, will I receive a refund?
Yes! The majority of hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winnetka.
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 coffee shops. Top sights around the area include Wrigley Field, Naval Base Great Lakes and Michigan Avenue. In Winnetka, there are 2 hotels and other accommodation options to choose from. Find out more about Winnetka.
What should I see while I'm in Winnetka?
Favourite 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. Take a look at what more there is to see and do in Expedia's Winnetka guide.
How can I get around Winnetka?
To venture out into 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 in Winnetka?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Winnetka is 1216 mm.

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