Search Winnetka hotels

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Winnetka

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2053)
"Beautiful property, will definitely stay there again."
The price is NZ$451
includes taxes & fees
21 Aug - 22 Aug
Sable at Navy Pier Chicago, Curio Collection by Hilton

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2488)
"Amazing Stay!"
The price is NZ$424
includes taxes & fees
3 Aug - 4 Aug
Swissotel - Chicago

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1501)
"Great location and rooms "
The price is NZ$439
includes taxes & fees
27 July - 28 July
Loews Chicago Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1941)
"I loved the room pool view, the restaurants & the location "
The price is NZ$310
includes taxes & fees
21 Aug - 22 Aug
DoubleTree by Hilton Chicago - Magnificent Mile

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very good, (1545)
"Great location and views from rooms were beautiful. "
The price is NZ$408
includes taxes & fees
17 Aug - 18 Aug
Radisson Blu Aqua Hotel Chicago

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1826)
"Nice place to stay and explore Chicago."
The price is NZ$501
includes taxes & fees
3 Aug - 4 Aug
Fairmont Chicago at Millennium Park

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2771)
"Great location and friendly staff"
The price is NZ$295
includes taxes & fees
10 Aug - 11 Aug
Aloft Chicago Mag Mile

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1013)
"Great location and hotel "
The price is NZ$307
includes taxes & fees
5 Aug - 6 Aug
Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1960)
"Great stay! "
The price is NZ$266
includes taxes & fees
17 Aug - 18 Aug
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3321)
"Great stay for a short weekend"
The price is NZ$468
includes taxes & fees
21 Aug - 22 Aug
Hyatt Regency Chicago

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2526)
"Great location and accommodations! Would definitely stay here again. "
The price is NZ$279
includes taxes & fees
10 Aug - 11 Aug
Hilton Chicago/Magnificent Mile Suites

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1909)
"It was a wonderful stay"
The price is NZ$285
includes taxes & fees
24 Aug - 25 Aug
Millennium Knickerbocker Chicago

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1030)
"Best place we have stayed in Chicago in a long time. "
The price is NZ$377
includes taxes & fees
27 July - 28 July
Hyatt Centric Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1122)
"Great stay"
The price is NZ$312
includes taxes & fees
4 Aug - 5 Aug
The Chicago Hotel Collection - Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1696)
"I really enjoyed my stay here, the staff was very pleasant and the rooms great!"
Hotel Saint Clair- Magnificent Mile

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2229)
"Great location, great breakfast and perfect rooms."
The price is NZ$357
includes taxes & fees
24 Aug - 25 Aug
Hotel Riu Plaza Chicago

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2584)
"Excellent Hotel!!"
The price is NZ$239
includes taxes & fees
24 Aug - 25 Aug
Best Western Grant Park Hotel

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8962)
"Great place to stay."
The price is NZ$344
includes taxes & fees
4 Aug - 5 Aug
Congress Plaza Hotel

Le Méridien Essex Chicago

4.0 star property
8.6 out of 10, Excellent, (1008)
"The staff was so friendly, accommodations were modern and well appointed, a wonderful location with surprisingly good food in the attached restaurant "
The price is NZ$305
includes taxes & fees
24 Aug - 25 Aug
Le Méridien Essex Chicago

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (2101)
"Great hotel"
The price is NZ$527
includes taxes & fees
22 Aug - 23 Aug
InterContinental Chicago Magnificent Mile by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near top Winnetka attractions

Learn more about Winnetka

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

Top Winnetka Hotel 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 InterContinental Chicago Magnificent Mile by IHG and Hilton Chicago/Magnificent Mile Suites. See all available top hotels, or vacation rentals in Winnetka.

What are some of the best holiday rentals that Winnetka has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Winnetka is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave. 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 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.