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Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

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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, (2,508 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is NZ$449
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Room service – dining

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,835 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is NZ$308
includes taxes & fees
25 May - 26 May
The Wade
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,625 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is NZ$496
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,334 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is NZ$402
includes taxes & fees
25 May - 26 May
Swissotel - Chicago
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,474 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is NZ$325
includes taxes & fees
26 May - 27 May
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
8.2 out of 10, Very good, (2,858 reviews)
"Best hotel breakfast around...for free! Excellent buffet, and cook to order omelets are restaurant quality"
United States
Michael
The price is NZ$389
includes taxes & fees
27 May - 28 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lunch and dinner served

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,942 reviews)
"Great Hotel "
United States
Dylan
The price is NZ$455
includes taxes & fees
25 May - 26 May
Radisson Blu Aqua Hotel Chicago
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,163 reviews)
"Great place"
United States
JOSE
The price is NZ$495
includes taxes & fees
26 May - 27 May
Fairmont Chicago at Millennium Park
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,238 reviews)
"Nice place to stay"
United States
Jimmie
The price is NZ$322
includes taxes & fees
26 May - 27 May
Aloft by Marriott Chicago Mag Mile
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,271 reviews)
"Great location, clean room, comfortable beds. Love this hotel and will stay here again and again!"
United States
Ping
The price is NZ$268
includes taxes & fees
25 May - 26 May
Ivy Boutique Hotel
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,455 reviews)
"Perfect location, very comfortable rooms, friendly staff."
United States
Annabelle
The price is NZ$311
includes taxes & fees
25 May - 26 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,011 reviews)
"All around great stay. "
United States
Nicholas
The price is NZ$250
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,319 reviews)
"Beautiful Hotel great location"
United States
Nereida
The price is NZ$322
includes taxes & fees
25 May - 26 May
Hilton Chicago/Magnificent Mile Suites
Shopping centre

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,969 reviews)
"Loved everything including location and food options. Great hotel. "
United States
Eileen
The price is NZ$316
includes taxes & fees
24 May - 25 May
Millennium Hotel Knickerbocker Chicago
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,527 reviews)
"Very good place to stay. I really liked the lobby — it’s very spacious. The lobby design is also very open and artistic."
Canada
Tong
The price is NZ$504
includes taxes & fees
25 May - 26 May
Hyatt Regency Chicago
Exterior

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,092 reviews)
"Great stay!"
United States
Milo
The price is NZ$414
includes taxes & fees
27 May - 28 May
Hyatt Centric Chicago Magnificent Mile
Premium bedding, in-room safe, desk, blackout curtains

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,912 reviews)
"Great Place to stay while in Chicago."
United States
Stacy
The price is NZ$330
includes taxes & fees
25 May - 26 May
Courtyard by Marriott Chicago Magnificent Mile
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,447 reviews)
"Great stay"
United States
Christa
The price is NZ$246
includes taxes & fees
25 May - 26 May
The Chicago Hotel Collection - Magnificent Mile
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,201 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is NZ$350
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,171 reviews)
"The bar was very welcoming and the historic ambience and location was exceptional"
United States
Patricia
The price is NZ$270
includes taxes & fees
25 May - 26 May
Congress Plaza Hotel
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

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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Breakfast bar was very good just need 0to go cups for coffee.I'm "
Allison 4-night trip
Posted 7 hours ago
Hotel Riu Plaza Chicago

More cheap accommodation in Winnetka

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

22 West Algonquin Road Arlington Heights IL
The price is NZ$110 per night from 5 June to 6 June
NZ$110
5 June - 6 June
includes taxes & fees
5.4/10 (1,002 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 Hotel Riu Plaza Chicago and The Chicago Hotel Collection - Magnificent Mile. See all available top hotels, or vacation rentals in Winnetka.
What are some of the best holiday rentals that Winnetka has to offer?
ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Winnetka is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 Navy Pier. 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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