Search Winnetka hotels

  • 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
5 Apr - 6 Apr
Tomorrow
6 Apr - 7 Apr
Next weekend
10 Apr - 12 Apr
In two weeks
17 Apr - 19 Apr

Filter by

Guest rating
Guest rating
Star rating

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, (2,437 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is NZ$425
includes taxes & fees
6 Apr - 7 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,723 reviews)
"Great hotel "
United States
Marina
The price is NZ$316
includes taxes & fees
28 Apr - 29 Apr
Hotel Riu Plaza Chicago
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,162 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is NZ$250
includes taxes & fees
12 Apr - 13 Apr
Aloft Chicago Mag Mile
Shared kitchen

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (530 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is NZ$164
includes taxes & fees
13 Apr - 14 Apr
FOUND Hotel Chicago River North
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,848 reviews)
"Was nice! "
Canada
Emilie
The price is NZ$189
includes taxes & fees
7 Apr - 8 Apr
Freehand Chicago
Lobby

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,060 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is NZ$244
includes taxes & fees
26 Apr - 27 Apr
River Hotel
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,027 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is NZ$224
includes taxes & fees
16 Apr - 17 Apr
Congress Plaza Hotel
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,057 reviews)
"For the price, it was a very nice a room and location. "
United States
Anna
The price is NZ$191
includes taxes & fees
8 Apr - 9 Apr
Central Loop Hotel
Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,133 reviews)
"Nice place to stay. "
United States
Akanksha
The price is NZ$254
includes taxes & fees
26 Apr - 27 Apr
The Godfrey Hotel Chicago
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, (1,944 reviews)
"Hotel was really nice"
United States
LaCarr
The price is NZ$260
includes taxes & fees
30 Apr - 1 May
Hilton Garden Inn Chicago Downtown South Loop
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,240 reviews)
"Great stay!"
United States
Jessica
The price is NZ$275
includes taxes & fees
12 Apr - 13 Apr
Silversmith Hotel Chicago Downtown
Lobby lounge

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,005 reviews)
"Great views close to museums and great restaurants "
United States
Blanca L
The price is NZ$326
includes taxes & fees
26 Apr - 27 Apr
Le Méridien Essex Chicago
Lobby sitting area

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1,874 reviews)
"Great location and a very high class hotel."
United States
Cornelius
The price is NZ$188
includes taxes & fees
6 Apr - 7 Apr
Hotel Saint Clair- Magnificent Mile
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, (1,353 reviews)
"Very beautiful place to stay"
United States
angie
The price is NZ$230
includes taxes & fees
19 Apr - 20 Apr
The Chicago Hotel Collection Ambassador Gold Coast
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,005 reviews)
"Super cute hotel. Great bar and food "
United States
Patricia
The price is NZ$365
includes taxes & fees
12 Apr - 13 Apr
The Hoxton Chicago
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, (2,145 reviews)
"Great stay!"
United States
Hannah
The price is NZ$225
includes taxes & fees
6 Apr - 7 Apr
Club Quarters Hotel Wacker at Michigan, Chicago
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,723 reviews)
"We love staying here "
United States
Carrie
The price is NZ$462
includes taxes & fees
10 Apr - 11 Apr
Hilton Chicago
Exterior

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,399 reviews)
"Loved this hotel!"
United States
Ellen
The price is NZ$264
includes taxes & fees
12 Apr - 13 Apr
DoubleTree by Hilton Chicago - Magnificent Mile
Nightclub

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,421 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is NZ$221
includes taxes & fees
19 Apr - 20 Apr
Club Quarters Hotel, Central Loop, Chicago
Presidential Suite, 1 Bedroom, Non Smoking

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,580 reviews)
"Clean room, great location! Walked just about every where. Shower was amazing and room lights were on dimmers which is great for night time with children. I would definitely stay at this location again. Great price for a big city and location!"
United States
Holly
The price is NZ$316
includes taxes & fees
6 Apr - 7 Apr
Hotel 55 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.
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

This lakefront sanctuary offers a serene escape with pristine sandy shores and Lake Michigan views. Enjoy a peaceful afternoon in the adjacent park with its well-maintained picnic areas and playground.
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"My daughter and I stayed at the Hilton to go see Hamilton in the state was amazing amazing. The hotel is located in a great spot walkable to just about anything friendly staff very attentive. I will be coming back."
Danielle 3-night trip
Posted 1 hour ago
Hilton Chicago/Magnificent Mile Suites

More cheap accommodation in Winnetka

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL
The price is NZ$104 per night from 19 Apr to 20 Apr
NZ$104
19 Apr - 20 Apr
includes taxes & fees
7.8/10 Good! (1,904 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 Hilton Chicago/Magnificent Mile Suites and Embassy Suites by Hilton Chicago Downtown River North. See all available top hotels, or vacation rentals in Winnetka.
What are some of the best holiday rentals that Winnetka has to offer?
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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! 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. There are 4558 hotels and other accommodation options in the surrounding area. 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