Winnetka Hotels from S$115

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
30 Apr - 1 May
Tomorrow
1 May - 2 May
This weekend
2 May - 4 May
Next weekend
9 May - 11 May

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winnetka hotels

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, (2058)
"Great location, nice rooms with views"
The price is S$309
includes taxes & fees
27 May - 28 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Front of property – evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2078)
"Great place to stay. "
The price is S$282
includes taxes & fees
11 May - 12 May
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1446)
"Very good hotel and excellent location. "
The price is S$346
includes taxes & fees
11 May - 12 May
Loews Chicago Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1844)
"It was a great stay and walking distance to everything "
The price is S$232
includes taxes & fees
27 May - 28 May
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1423)
"Great location and friendly staff."
The price is S$335
includes taxes & fees
9 May - 10 May
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Front of property – evening/night

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1692)
"Had a great stay I loved the environment and views "
The price is S$313
includes taxes & fees
2 May - 3 May
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2714)
"A fun, comfortable hotel in a great location!"
The price is S$161
includes taxes & fees
26 May - 27 May
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.6 out of 10, Excellent, (1001)
"Front desk staff was polite. Property was clean. Great stay."
The price is S$193
includes taxes & fees
28 May - 29 May
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1716)
"Great Location and exceptional staff. "
The price is S$190
includes taxes & fees
26 May - 27 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3212)
"Great hotel "
The price is S$354
includes taxes & fees
26 May - 27 May
Hyatt Regency Chicago
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.4 out of 10, Very good, (1763)
"Very nice stay, "
The price is S$169
includes taxes & fees
14 May - 15 May
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Lobby

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1017)
"Great place to stay"
The price is S$283
includes taxes & fees
26 May - 27 May
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Restaurant

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1020)
"Loved the location "
The price is S$152
includes taxes & fees
7 May - 8 May
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1565)
"Great place would stay again "
The price is S$171
includes taxes & fees
12 May - 13 May
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (1783)
" Great place to stay!"
The price is S$268
includes taxes & fees
11 May - 12 May
Hotel Riu Plaza Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2511)
"Nice stay, close to CTA and walkable to great dining and shops."
The price is S$137
includes taxes & fees
26 May - 27 May
Best Western Grant Park Hotel
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8726)
"Great stay"
The price is S$195
includes taxes & fees
11 May - 12 May
Congress Plaza Hotel
Le Méridien Essex Chicago
City view

Le Méridien Essex Chicago

4.0 star property
8.6 out of 10, Excellent, (1001)
"This is a great location and stay . "
The price is S$233
includes taxes & fees
27 May - 28 May
Le Méridien Essex Chicago
InterContinental Chicago Magnificent Mile by IHG
Exterior

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (1795)
"Great stay!"
The price is S$351
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG
Warwick Allerton - Chicago
Front of property

Warwick Allerton - Chicago

4.0 star property
8.2 out of 10, Very good, (2850)
"Great location "
The price is S$178
includes taxes & fees
11 May - 12 May
Warwick Allerton - 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.
Don't see what you're looking for?
See all available properties in Winnetka
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Winnetka

Explore Winnetka: its forests, sports, coffee and more!

See all hotels in Winnetka

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 Congress Plaza 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 are some accommodation options with pools in Winnetka?

DoubleTree by Hilton Chicago - Magnificent Mile: 4-star hotel, 4-minute walk from Michigan Avenue. Features a rooftop terrace, an outdoor pool and LED TVs. Loews Chicago Hotel and Embassy Suites Chicago Downtown Magnificent Mile are two additional hotels with an on-site pool. View all hotels with pools 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.