Winnetka Hotels from S$76

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9 Jul - 10 Jul
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10 Jul - 11 Jul
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11 Jul - 13 Jul
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Top 10 trending Winnetka hotels

DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1894)
"I loved the room pool view, the restaurants & the location "
The price is S$292
includes taxes & fees
6 Aug - 7 Aug
DoubleTree by Hilton Chicago - Magnificent Mile
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4330)
"The hotel was great from the staff to the location "
The price is S$269
includes taxes & fees
10 Jul - 11 Jul
River Hotel
Eurostars Magnificent Mile
Reception hall

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3017)
"Loved our stay! "
The price is S$216
includes taxes & fees
27 Jul - 28 Jul
Eurostars 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, (2053)
"Amazing property clean comfy bedding and wonderful views"
The price is S$375
includes taxes & fees
13 Jul - 14 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3315)
"Friendly staff, great bar and lounge areas."
The price is S$229
includes taxes & fees
7 Aug - 8 Aug
citizenM Chicago Downtown
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1003)
"Reasonably priced, cleanliness of room, restaurant and bar within, and staff was friendly. Would highly recommend this Hotel! "
The price is S$188
includes taxes & fees
10 Jul - 11 Jul
Best Western River North Hotel
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1234)
"Easy check in and check out, close to a lot of restaurants, very walkable! "
The price is S$215
includes taxes & fees
13 Jul - 14 Jul
Crowne Plaza Chicago West Loop by IHG
Aloft Chicago Mag Mile
Exterior

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2753)
"Good location, comfortable bed, staff very nice and helpful!"
The price is S$296
includes taxes & fees
6 Aug - 7 Aug
Aloft Chicago Mag Mile
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, (3504)
"Great location and the reception desk was very professional. "
The price is S$270
includes taxes & fees
10 Jul - 11 Jul
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8922)
"Great location, beautiful hotel "
The price is S$266
includes taxes & fees
4 Aug - 5 Aug
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2410)
"Friendly staff, beautiful views, excellent location "
The price is S$268
includes taxes & fees
6 Aug - 7 Aug
Hilton Chicago/Magnificent Mile Suites
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2040)
"Stayed many times, great fun!"
The price is S$190
includes taxes & fees
6 Aug - 7 Aug
Freehand Chicago
Holiday Inn & Suites Chicago - Downtown by IHG
Pool

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very good, (1002)
"Nice place to stay"
The price is S$255
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn & Suites Chicago - Downtown by IHG
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, (1879)
"Great stay! "
The price is S$205
includes taxes & fees
6 Aug - 7 Aug
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
The Whitehall Hotel, BW Premier Collection
1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3465)
"Great stay "
The price is S$225
includes taxes & fees
6 Aug - 7 Aug
The Whitehall Hotel, BW Premier Collection
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, (2416)
"Great hotel"
The price is S$251
includes taxes & fees
10 Jul - 11 Jul
La Quinta Inn & Suites by Wyndham Chicago Downtown
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (509)
"The rooms were excellent"
The price is S$181
includes taxes & fees
10 Jul - 11 Jul
The Chicago Hotel Collection River North
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2226)
"Great place to stay!"
The price is S$201
includes taxes & fees
10 Jul - 11 Jul
Travelodge by Wyndham Downtown Chicago
Palmer House a Hilton Hotel
Meeting facility

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1776)
"Love our stay here "
The price is S$295
includes taxes & fees
8 Aug - 9 Aug
Palmer House a Hilton Hotel
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1649)
"Great stay"
Hotel Saint Clair- Magnificent Mile
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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Learn more about Winnetka

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

See all hotels in Winnetka

Frequently asked questions

What's the best place to stay in Winnetka?

Located 16 mi (25.8 km) from the heart of Winnetka, InterContinental Chicago Magnificent Mile by IHG 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 Congress Plaza Hotel. 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.