Winnetka Hotels from S$67

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winnetka hotels

Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (3072)
"The hotel has a restaurant on the first floor with patio seating and great views."
The price is S$164
includes taxes & fees
10 Nov - 11 Nov
Eurostars Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2086)
"Great hotel"
The price is S$242
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2181)
"Great hotel "
The price is S$287
includes taxes & fees
9 Nov - 10 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4735)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is S$268
includes taxes & fees
23 Oct - 24 Oct
River Hotel
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2855)
"Had a great stay!"
The price is S$210
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3071)
"Our stay was great"
The price is S$219
includes taxes & fees
9 Nov - 10 Nov
Hilton Chicago/Magnificent Mile Suites
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3931)
"Great place to stay. "
The price is S$212
includes taxes & fees
10 Nov - 11 Nov
citizenM Chicago Downtown
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9378)
"Beautiful hotel!"
Congress Plaza Hotel
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2253)
"We loved this hotel it was beautiful and convenient . "
The price is S$318
includes taxes & fees
23 Oct - 24 Oct
Hilton Chicago
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2450)
"Great place"
The price is S$124
includes taxes & fees
11 Nov - 12 Nov
Freehand Chicago
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, (4063)
"We definitely will stay there again place was very nice "
The price is S$245
includes taxes & fees
2 Nov - 3 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1022)
"Great stay"
The price is S$154
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2579)
"Great place to stay "
The price is S$261
includes taxes & fees
9 Nov - 10 Nov
Hotel Riu Plaza Chicago
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (272)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is S$119
includes taxes & fees
9 Nov - 10 Nov
FOUND Hotel Chicago River North
voco Chicago Downtown - Riverwalk by IHG
Bar (on property)

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
8.8 out of 10, Excellent, (3200)
"Great stay "
The price is S$242
includes taxes & fees
9 Nov - 10 Nov
voco Chicago Downtown - Riverwalk by IHG
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2175)
"It was an amazing stay!"
The price is S$277
includes taxes & fees
9 Nov - 10 Nov
Hyatt Centric The Loop Chicago
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (2015)
"Great place to stay "
Silversmith Hotel Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2572)
"Good place to stay"
The price is S$241
includes taxes & fees
9 Nov - 10 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
The Whitehall Hotel, BW Premier Collection
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3640)
"Great location , good breakfast"
The price is S$149
includes taxes & fees
11 Nov - 12 Nov
The Whitehall Hotel, BW Premier Collection
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.4 out of 10, Good, (2405)
"Comfortable bed, bright room, good shower, very accessible location."
The price is S$154
includes taxes & fees
10 Nov - 11 Nov
Travelodge by Wyndham Downtown 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Top Winnetka Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Great location"
Patricia 3-night trip
Posted 23 hours ago
Crowne Plaza Chicago West Loop by IHG

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$142 per night from 19 Oct to 20 Oct
S$142
19 Oct - 20 Oct
includes taxes & fees
8.2/10 Very Good! (1,991 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 traveller data. Other good choices for your trip to the area are Freehand Chicago and Embassy Suites by Hilton Chicago Downtown River North. 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.

Explore a world of travel with Expedia