Hotels in Winnetka

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
May 10 - May 11
Tomorrow
May 11 - May 12
Next weekend
May 15 - May 17
In two weeks
May 22 - May 24

Where to stay in Winnetka?

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, (2,500 reviews)
Experience the unique charm of this waterfront hotel with panoramic Lake Michigan vistas. Just steps from Navy Pier, enjoy Latin American cuisine at Lirica or unwind at one of 2 bars. A 24-hour fitness center and convenient access to Michigan Avenue complete your Chicago adventure.
The price is $190
$260 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby
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, (1,431 reviews)
Immerse yourself in this historic Gold Coast retreat near Michigan Avenue and Oak Street Beach. Enjoy robust coffee at the on-site café, workout anytime, and experience the quiet, relaxing atmosphere that travelers consistently praise.
The price is $144
$171 total
includes taxes & fees
May 12 - May 13
The Chicago Hotel Collection Ambassador Gold Coast
Indoor pool
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,437 reviews)
Immerse yourself in luxury at this storied Chicago hotel. Just steps from Millennium Park and Monroe Station, this classic retreat features a full-service spa, indoor pool, and elegant bar. Travelers praise the central location and helpful staff.
The price is $143
$199 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel
Reception hall
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,528 reviews)
Discover a boutique hotel near Chicago's iconic attractions, with a full-service spa offering massages and scrubs. Just 3 minutes from Chicago Station, this sophisticated retreat features clean rooms, helpful staff, and easy access to the Riverwalk.
The price is $160
$190 total
includes taxes & fees
May 12 - May 13
Eurostars Magnificent Mile
Exterior
Arlo Chicago
Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,117 reviews)
Immerse yourself in downtown Chicago at this well-positioned hotel, steps from Millennium Park and Michigan Avenue. The American restaurant About Last Knife serves three meals daily while the 24-hour fitness center keeps you energized. Chicago Riverwalk and Chicago Theatre are both within a 10-minute walk.
The price is $108
$159 total
includes taxes & fees
May 25 - May 26
Arlo Chicago
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, (1,398 reviews)
Immerse in Chicago's vibrant energy at this boutique hotel. Steps from Michigan Avenue and Water Tower Place, enjoy clean rooms with city vistas. Grab breakfast at the Lobby Bar before exploring nearby Lake Michigan and Chicago Riverwalk.
The price is $123
$146 total
includes taxes & fees
May 12 - May 13
The Chicago Hotel Collection - Magnificent Mile
Lobby
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (10,205 reviews)
This historic hotel offers majestic lake views and is steps from Columbia College Chicago. Enjoy meals at 2 restaurants or the café, then unwind at the bars. With train stations nearby and helpful staff, you'll experience both charm and convenience.
The price is $135
$161 total
includes taxes & fees
May 12 - May 13
Congress Plaza Hotel
Lobby
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,262 reviews)
Just steps from Madison-Wabash Station, this boutique hotel offers easy access to Millennium Park and Michigan Avenue. Admire the historic Art Deco architecture while enjoying clean rooms, a 24-hour fitness center, and attentive staff praised by travelers.
The price is $135
$191 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown
Exterior detail
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (599 reviews)
Located in Chicago's River North area, this inviting hotel offers free WiFi and 24-hour front desk service. Just 5 minutes from Merchandise Mart Station and a short stroll to State Street, you're perfectly positioned to explore Michigan Avenue and Chicago Riverwalk.
The price is $106
$124 total
includes taxes & fees
May 26 - May 27
FOUND Hotel Chicago River North
Interior detail
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,063 reviews)
The price is $133
$188 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop
2 restaurants, breakfast, lunch, dinner served; American cuisine
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,715 reviews)
Just steps from Chicago Riverwalk, this luxurious hotel offers 2 restaurants and 2 bars, including a stunning rooftop terrace. After a day of exploring nearby Michigan Avenue, unwind with deep-tissue massages at the on-site spa.
The price is $181
$245 total
includes taxes & fees
May 26 - May 27
LondonHouse Chicago, Curio Collection by Hilton
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,105 reviews)
The price is $141
$197 total
includes taxes & fees
May 25 - May 26
Hotel Riu Plaza Chicago
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,785 reviews)
This historic Chicago hotel features an indoor pool and health club just steps from Art Institute of Chicago. Enjoy panoramic lake views, dine at Herb N Kitchen, and walk to Millennium Park or catch the train at nearby Harrison Station.
The price is $130
$184 total
includes taxes & fees
May 25 - May 26
Hilton Chicago
Bar (on property)
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,055 reviews)
Experience Chicago from this central hotel, just minutes from Michigan Avenue and Riverwalk. Quiet rooms offer beautiful city views, while the 24-hour fitness center keeps your routine intact. With Red Line stations nearby, explore attractions effortlessly before unwinding at the hotel bar.
The price is $136
$191 total
includes taxes & fees
May 12 - May 13
Warwick Allerton - Chicago
Exterior
Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,518 reviews)
This boutique Chicago haven sits 10 minutes from Lake Michigan and State Street. The cafe transforms into an evening cocktail bar, while the full-service spa offers facials. Just 3 minutes from Clark-Division Station for easy city exploration.
The price is $110
$160 total
includes taxes & fees
May 25 - May 26
Claridge House Chicago, Tapestry Collection by Hilton
Exterior detail
The Emily Hotel
The Emily Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,325 reviews)
The price is $193
$229 total
includes taxes & fees
May 25 - May 26
The Emily Hotel
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine
The Hoxton Chicago
The Hoxton Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,013 reviews)
Dive into Chicago's vibrant scene at this West Loop hotel with a seasonal rooftop pool and Mediterranean dining at Cira. Just minutes from Millennium Park and Chicago Riverwalk, with 3 bars, free bikes, and easy access to Clinton Station.
The price is $229
$302 total
includes taxes & fees
May 25 - May 26
The Hoxton Chicago
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2,975 reviews)
Explore Michigan Avenue from this stylish hotel with a 24-hour fitness center and bar/lounge. Steps from Grand Station, it offers easy access to Chicago Riverwalk and Millennium Park, plus free WiFi and room service.
The price is $82
$116 total
includes taxes & fees
May 25 - May 26
Freehand Chicago
Lobby
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,237 reviews)
Discover urban bliss at this Chicago hotel with an indoor pool and American cuisine restaurant. Near Michigan Avenue and Riverwalk, with Grand Station just 9 minutes away. Guests love the comfortable beds, helpful staff, and prime location.
The price is $145
$172 total
includes taxes & fees
May 26 - May 27
Aloft Chicago Mag Mile
Executive lounge
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,158 reviews)
Tucked in downtown Chicago, this hotel offers a full-service spa and American cuisine at Lobby Bar. Just a 5-minute walk to Millennium Park and Michigan Avenue, with 2 bars/lounges and a 24-hour fitness center nearby.
The price is $192
$264 total
includes taxes & fees
May 26 - May 27
Fairmont Chicago at Millennium Park
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.
View all properties

Top landmarks in Winnetka

Chocolate Box

Chocolate Box is in the heart of Winnetka, so why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? If you have fun at Chocolate Box, you'll love Wagner Farm and North Shore Center for the Performing Arts, both located nearby.
See properties

Learn more about Winnetka

Winnetka is well-known for its attractions such as Lake Michigan and Chocolate Box.

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.

Check out reviews of Winnetka hotels guests love

River Hotel

River Hotel

10/10 Excellent
"Good for what you pay and the location can’t be beat."
Naser 2-night trip
Posted 1 hour ago
River Hotel

Frequently asked questions

Can I book refundable accommodations in Winnetka?
If you need the flexibility to change your plans to Winnetka, most accommodations offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winnetka be like during my visit?
The warmest months in Winnetka are usually July and August with an average temp of 70°F. January and February are the chilliest months when the average temp is 30°F. The rainiest months are May and June.
Why should I book my Winnetka hotel through Hotels.com?
There are plenty of reasons to book your Winnetka travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.