Winnetka Hotels from from S$61

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Our top choices for Winnetka hotels

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, (2,396 reviews)
"Great stay"
United States
Blake
The price is S$241
includes taxes & fees
24 Mar - 25 Mar
Sable at Navy Pier Chicago, Curio Collection by Hilton

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,195 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is S$226
includes taxes & fees
24 Mar - 25 Mar
Swissotel - Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,093 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is S$127
includes taxes & fees
5 Mar - 6 Mar
Aloft Chicago Mag Mile

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, (1,289 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is S$158
includes taxes & fees
2 Mar - 3 Mar
The Chicago Hotel Collection Ambassador Gold Coast

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,699 reviews)
"Thoroughly enjoyed my stay at The Wade"
United States
Danielle
The price is S$147
includes taxes & fees
2 Mar - 3 Mar
The Wade

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,415 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is S$220
includes taxes & fees
1 Mar - 2 Mar
Hotel Riu Plaza Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,317 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is S$255
includes taxes & fees
7 Mar - 8 Mar
Palmer House a Hilton Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9,937 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is S$400
includes taxes & fees
13 Mar - 14 Mar
Congress Plaza Hotel

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful place to stay, nice staff 🙏"
United States
Yu Ching Dexter
The price is S$244
includes taxes & fees
27 Feb - 28 Feb
The Blackstone, Autograph Collection

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,011 reviews)
"Location was great, staff was very friendly, and the rooms were clean. "
United States
Lori
The price is S$219
includes taxes & fees
18 Mar - 19 Mar
Staypineapple, An Iconic Hotel, The Loop

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (471 reviews)
"Amazing staff and very clean, modern rooms!"
United States
genevieve
The price is S$90
includes taxes & fees
2 Mar - 3 Mar
FOUND Hotel Chicago River North

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, (1,868 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is S$142
includes taxes & fees
1 Mar - 2 Mar
Hilton Garden Inn Chicago Downtown South Loop

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,695 reviews)
"Great location and overall great hotel."
United States
Fernando
The price is S$204
includes taxes & fees
17 Mar - 18 Mar
L7 Chicago by LOTTE

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,779 reviews)
"I enjoyed my stay"
United States
Emily
The price is S$121
includes taxes & fees
2 Mar - 3 Mar
Freehand Chicago

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,400 reviews)
"Super comfy beds, helpful staff, free coffee and snacks and an amazing location "
United States
Stephanie
The price is S$171
includes taxes & fees
27 Feb - 28 Feb
Hyatt Centric The Loop Chicago

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1,217 reviews)
"Amazing stay "
United States
Napoleon
The Chicago Hotel Collection - Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,838 reviews)
"The staff and the cleanliness of the Hotel was amazing and the views where great!!"
United States
Oliver
The price is S$154
includes taxes & fees
4 Mar - 5 Mar
Hilton Chicago/Magnificent Mile Suites

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,001 reviews)
"Super clean rooms , nice down stairs , loved the bathroom "
United States
Kaiya
The price is S$162
includes taxes & fees
8 Mar - 9 Mar
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,266 reviews)
"Great stay "
United States
Kylee
The price is S$166
includes taxes & fees
3 Mar - 4 Mar
Eurostars Magnificent Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,144 reviews)
"I always stay here when in town. "
United States
Jeffrey
Ivy Boutique 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

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.

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.

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