Winnetka Hotels from S$57

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26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

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Top 10 trending Winnetka hotels

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, (2158)
"Great stay "
United States
Melinda
The price is S$149
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3131)
"Location was great "
United States
Hamik
The price is S$163
includes taxes & fees
16 Dec - 17 Dec
Eurostars Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4845)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is S$135
includes taxes & fees
27 Nov - 28 Nov
River Hotel
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, (2247)
"Room was spotless…staff was great!"
United States
Tamika
The price is S$180
includes taxes & fees
16 Dec - 17 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2938)
"Great location!!"
United States
sarah e
The price is S$138
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3377)
"Great stay!"
United States
Rose
The price is S$127
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2320)
"Clean Rooms & very nice staff"
United States
Teresa
The price is S$200
includes taxes & fees
20 Dec - 21 Dec
Hilton Chicago
Terrace/patio
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4083)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is S$164
includes taxes & fees
24 Dec - 25 Dec
citizenM Chicago Downtown
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1709)
"The location was great!!"
United States
Yvette
The price is S$183
includes taxes & fees
20 Dec - 21 Dec
Crowne Plaza Chicago West Loop by IHG
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, (4200)
"Great location. "
United States
Rodger
The price is S$122
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (340)
"love this place definitely coming back !"
United States
Dayanara
The price is S$107
includes taxes & fees
7 Dec - 8 Dec
FOUND Hotel Chicago River North
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2859)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is S$175
includes taxes & fees
8 Dec - 9 Dec
Hotel Riu Plaza Chicago
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2605)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is S$145
includes taxes & fees
7 Dec - 8 Dec
Freehand Chicago
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
Downtown Chicago
7.8 out of 10, Good, (1018)
"Staff was very friendly "
United States
david
The price is S$133
includes taxes & fees
9 Dec - 10 Dec
Best Western River North Hotel
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9659)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is S$157
includes taxes & fees
27 Nov - 28 Nov
Congress Plaza Hotel
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2088)
"Lovely hotel in a great spot!"
United States
Natasha
The price is S$148
includes taxes & fees
21 Dec - 22 Dec
Silversmith Hotel Chicago Downtown
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1731)
"Clean room, great hot tub."
United States
SHARON
The price is S$121
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown South Loop
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1013)
"Really great location and warm and friendly staff"
United Kingdom
David
The price is S$155
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn & Suites Chicago - Downtown by IHG
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2099)
"Great place to stay."
United States
Aaron
The price is S$190
includes taxes & fees
21 Dec - 22 Dec
Palmer House a Hilton Hotel
Exterior
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2633)
"Enjoyed my stay here. "
United States
Vai
The price is S$180
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Chicago Downtown
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.
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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.
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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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"The room had a beautiful view!! It was very clean, and cleaned everyday. The staff was always happy and very helpful. Definitely recommend this hotel if you want to stay downtown. "
Andrea 4-night trip
Posted 6 hours ago
The Royal Sonesta Chicago Downtown

More cheap stays 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 S$120 per night from 27 Nov to 28 Nov
S$120
27 Nov - 28 Nov
includes taxes & fees
8.2/10 Very Good! (2,138 reviews)

Frequently asked questions

What's the best place to stay in Winnetka?
Located 15.9 mi (25.5 km) from the heart of Winnetka, Embassy Suites by Hilton Chicago Downtown River North is a top choice for your stay, based on our traveller data. Other good choices for your trip to the area are Palmer House a Hilton Hotel and Hilton Chicago/Magnificent Mile Suites. See all available top hotels, or 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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