Winnetka Hotels from S$72

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Check Winnetka hotel prices

Tonight
24 Dec - 25 Dec
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25 Dec - 26 Dec
This weekend
27 Dec - 29 Dec
Next weekend
3 Jan - 5 Jan

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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, (2032)
"The views were absolutely beautiful and every thing was modern, clean. It was truly a great place to stay. The sunset and the sunrise were unbelievable. Definitely would stay again"
The price is S$182
includes taxes & fees
8 Jan - 9 Jan,2025
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, (1915)
"Views were unbelievable! No streaming services were available, and the breakfast server in part was abrupt, but overall, it was a great stay."
The price is S$269
includes taxes & fees
6 Jan - 7 Jan,2025
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1418)
"Always a great stay. Very accommodating and helpful. We received $50 in credits which was very nice. Good location and convenient to most every thing. "
The price is S$265
includes taxes & fees
12 Jan - 13 Jan,2025
Loews Chicago Hotel
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2547)
"Hello team and hope all is well. The staff at the front desk,,,, hands down was the best in a long time. Not the best at names: Josh/Justin greeting people and letting people know about the deals. Candy & Candace were the best, they had everyone happy and were so helpful. NOT GOOD- Parking at the hotel does not need to be so high for folks that stay with you. The team and I are looking where to stay on the next trip. Patric"
The price is S$194
includes taxes & fees
21 Jan - 22 Jan,2025
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1740)
"Staff and property were both amazing!"
The price is S$145
includes taxes & fees
5 Jan - 6 Jan,2025
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
8.4 out of 10, Very good, (1418)
"This is the second year we have stayed here. We like the convenience of the location, the quality of the room, and the friendliness of the staff. They are very accommodating and our perks as a VIP Member were appreciated. Our room had a view of Millennium Park, The bed was very comfortable and the generous bathroom with a soaker tub and enormous walk in shower was great. This is a full service hotel with a lounge, restaurant, coffee bar and health and fitness amenities. Walking distance to...
The price is S$259
includes taxes & fees
19 Jan - 20 Jan,2025
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, (1561)
"Christmas decorations were beautiful! Everything from the hotel was just perfect!"
The price is S$311
includes taxes & fees
2 Jan - 3 Jan,2025
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Exterior

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2454)
"."
The price is S$139
includes taxes & fees
1 Jan - 2 Jan,2025
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.4 out of 10, Very good, (1001)
"good "
The price is S$106
includes taxes & fees
21 Jan - 22 Jan,2025
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.2 out of 10, Very good, (1545)
".."
The price is S$161
includes taxes & fees
5 Jan - 6 Jan,2025
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, (3110)
"I recently stayed at the Hyatt for my 32th anniversary and it exceeded my expectations. The hotel was not only beautiful but also impeccably clean, which made my stay even more enjoyable. The staff was incredibly friendly and attentive, always ready to assist with a smile. I also loved the view of the city from my room. It was absolutely breathtaking! Waking up to such a stunning skyline made my stay even more memorable. The panoramic view added a special touch to my experience, allowing me to...
The price is S$275
includes taxes & fees
6 Jan - 7 Jan,2025
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (1873)
"First time in the city. Staff was so helpful. Everything was clean. Very convenient parking and near everything in walking distance "
The price is S$164
includes taxes & fees
12 Jan - 13 Jan,2025
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.4 out of 10, Very good, (1772)
"Outstanding "
The price is S$172
includes taxes & fees
2 Jan - 3 Jan,2025
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Lobby

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1079)
"Everything was spot on, friendly service, lovely bar and room."
The price is S$243
includes taxes & fees
24 Jan - 25 Jan,2025
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Outdoor banquet area

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.6 out of 10, Good, (1005)
"Great "
The price is S$174
includes taxes & fees
8 Jan - 9 Jan,2025
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.0 out of 10, Very good, (1471)
"Clean rooms"
The price is S$126
includes taxes & fees
7 Jan - 8 Jan,2025
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.2 out of 10, Wonderful, (1233)
"Spacious room. Great breakfast options. Nice stay in downtown "
The price is S$221
includes taxes & fees
2 Jan - 3 Jan,2025
Hotel Riu Plaza Chicago
The Blackstone, Autograph Collection
Lobby

The Blackstone, Autograph Collection

4.0 star property
9.0 out of 10, Wonderful, (1000)
"From the second we arrived, we were greeted and helped with our luggage inside the front desk. People were efficient and friendly and knowledgeable and asked about recommendations.. room was plenty big enough large bathroom. Ate at the restaurant on site very delicious. Everything just went very well and the rate was really good."
The price is S$202
includes taxes & fees
19 Jan - 20 Jan,2025
The Blackstone, Autograph Collection
Best Western Grant Park Hotel
Exterior

Best Western Grant Park Hotel

2.5 star property
8.0 out of 10, Very good, (2517)
"Great location, definitely satisfied 8.5/10."
The price is S$107
includes taxes & fees
6 Jan - 7 Jan,2025
Best Western Grant Park Hotel
Congress Plaza Hotel
Exterior

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8284)
"This is a very old property which is part of it's charm. Water pressure in the shower was very limited. Accomodations are simple. Really liked new vinyl flooring in room with throw rug. Much better than carpeting. I will return. "
The price is S$166
includes taxes & fees
1 Jan - 2 Jan,2025
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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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 Embassy Suites by Hilton Chicago Downtown River North and River 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 Naval Base Great Lakes, Michigan Avenue and Wrigley Field. 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 Naval Base Great Lakes and Michigan Avenue 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.