Find hotels in Winnetka, IL from $56

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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, (2272)
"Great staff and restaurants!!"
United States
Abigale
$122 nightly
The price is $143
Jan 15 - Jan 16, 2026
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1534)
"Great staff and great location. "
United States
Joe
$93 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Wade

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3040)
"Amazing staff and location beautiful hotel "
United States
RANDIE
$139 nightly
The price is $163
Jan 1 - Jan 2, 2026
Total with taxes and fees
Swissotel - Chicago

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (1579)
"Rooms were very nice and staff was great"
United States
Nancy
$155 nightly
The price is $181
Jan 20 - Jan 21, 2026
Total with taxes and fees
Sheraton Grand Chicago Riverwalk

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2754)
"Excellent place to stay "
United States
Teniesha
$109 nightly
The price is $127
Jan 6 - Jan 7, 2026
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2200)
"Great location, easy parking. "
United States
Maria
$85 nightly
The price is $100
Jan 4 - Jan 5, 2026
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1790)
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
$156 nightly
The price is $183
Dec 28 - Dec 29
Total with taxes and fees
Radisson Blu Aqua Hotel Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2966)
"Great place to stay"
United States
Elisha
$86 nightly
The price is $101
Jan 22 - Jan 23, 2026
Total with taxes and fees
Aloft Chicago Mag Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1048)
"I love this hotel "
United States
Tiara
$86 nightly
The price is $101
Jan 18 - Jan 19, 2026
Total with taxes and fees
Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2297)
"Excellent hotel. Loved staying there"
United States
cristina
$89 nightly
The price is $105
Jan 20 - Jan 21, 2026
Total with taxes and fees
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1000)
"Great hotel ,very clean ,very good breakfast !"
United States
Rey
$89 nightly
The price is $104
Jan 1 - Jan 2, 2026
Total with taxes and fees
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3389)
"The Hotel was amazing great location "
United States
Donnisha
$169 nightly
The price is $198
Jan 20 - Jan 21, 2026
Total with taxes and fees
Hyatt Regency Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3563)
"Great place to stay "
United States
RaShawna
$89 nightly
The price is $105
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2004)
"Great location, clean hotel"
United States
Andre
$106 nightly
The price is $124
Jan 4 - Jan 5, 2026
Total with taxes and fees
Millennium Knickerbocker Chicago

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1051)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
$123 nightly
The price is $144
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1619)
"Great stay!!"
United States
Adrian
$98 nightly
The price is $115
Jan 1 - Jan 2, 2026
Total with taxes and fees
Courtyard by Marriott Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1162)
"The room was spacious and clean and it was a good value."
United States
Dj
$125 nightly
The price is $147
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Chicago Hotel Collection - Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (1355)
"Wonderful location. "
United States
Karen
$89 nightly
The price is $105
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Chicago Downtown/Magnificent Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3046)
"Great rooms, love the bar and amazing breakfast!"
United States
Michelle
$124 nightly
The price is $145
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hotel Riu Plaza Chicago

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (2655)
"Great staff & Great location. "
United States
Gabrielle
$72 nightly
The price is $85
Jan 5 - Jan 6, 2026
Total with taxes and fees
Best Western Grant Park Hotel
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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 theater.

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.

Top Winnetka Hotel Reviews

More cheap stays in Winnetka

Hotels in Winnetka with star-rating

Find out more about Winnetka

Top reasons to visit Winnetka

  • Scenic Outdoor Activities: Winnetka offers beautiful beaches and urban parks, perfect for outdoor fun and relaxation.
  • Family-Friendly Atmosphere: The community provides a variety of family-oriented events and activities suitable for all ages.
  • Charming Neighborhoods: Explore picturesque neighborhoods with quaint parks and lovely city views.
  • Runnymede Recreation Center: A must-visit for recreational activities and community events.
  • Diverse Accommodations: Enjoy a range of lodging options, from cozy guesthouses to pet-friendly hotels.

Find great hotels near Winnetka

Discover the charm of Winnetka, Illinois, where a variety of accommodations await to enhance your stay. From cozy guesthouses to well-equipped hotels, you'll find options that cater to business travelers and those seeking a pet-friendly or LGBTQIA welcoming experience. Explore our selection of hotels near Winnetka, complete with reviews and amenities to ensure a memorable vacation.

  • Holiday Inn Chicago North-Evanston by IHG: This 3-star hotel offers a warm and welcoming environment, particularly for LGBTQIA travelers. Located 5 miles from Winnetka, it provides a business-themed experience with top-notch amenities tailored for business professionals. Guests can take advantage of the well-equipped Business Center, multiple Meeting Rooms, and accessible Conference Space. The hotel's affiliation with LGBTQI travel guides ensures an inclusive atmosphere, making it an excellent choice for work and leisure alike.
  • DoubleTree by Hilton Chicago - North Shore Conference Center: Experience luxury at this 4-star hotel, situated 4 miles from Winnetka. The DoubleTree combines a business-oriented focus with pet-friendly accommodations, making it perfect for both professionals and pet owners. With amenities such as a 24-hour Business Center, Conference Space, and multiple Meeting Rooms, it's ideal for corporate events. Plus, the hotel’s pet policy allows dogs and cats, enhancing the stay for those traveling with furry friends. The warm cookie welcome at check-in adds a personal touch to your stay.
  • Motel 6 Prospect Heights, IL: For budget-conscious travelers, Motel 6 Prospect Heights, located 8 miles from Winnetka, offers a no-frills, pet-friendly stay. Ideal for those traveling with pets, the motel permits free stays for pets under its generous policy. While it may lack the extensive amenities of higher-rated hotels, guests appreciate the clean, simple rooms and friendly service. This option is perfect for those seeking a straightforward, comfortable place to rest after a day of exploring the area.

Where to stay in Winnetka

Winnetka, Illinois, offers a delightful blend of family-friendly atmospheres and scenic outdoor experiences. Explore the charming neighborhoods, enjoy picturesque city views, and take advantage of convenient public transportation. Nearby areas provide vibrant urban vibes, perfect for romantic getaways or business trips. Whether you’re relaxing by the lake or strolling through quaint parks, Winnetka promises a memorable vacation for every traveler.

  • Chicago: As a vibrant metropolis, Chicago is a bustling hub that offers a diverse travel experience. Located approximately 20 miles south of Winnetka, this city comes alive during the summer months, attracting visitors looking for family-friendly activities, outdoor adventures, and iconic city experiences. Explore the renowned shopping districts, catch a game at one of the famous sports arenas, or enjoy a leisurely stroll along the lakeshore. Notable landmarks like Navy Pier and Millennium Park provide endless entertainment, making it a must-visit destination during your stay.
  • Northfield: Just a short drive from Winnetka, Northfield is a quaint village with a charming atmosphere. This community sees consistent visitor traffic year-round, with peaks in the spring and summer months. Families are drawn to its recreational areas and local events, while music concerts add a cultural flair. Enjoy shopping in unique boutiques or relax at the beautiful urban parks. Northfield's inviting environment makes it an ideal spot for those seeking a blend of city-themed experiences and outdoor relaxation.
  • Kenilworth: Located a mere 2 miles from Winnetka, Kenilworth is a picturesque city known for its scenic beauty and family-oriented charm. Visitors flock here during the spring and summer, drawn by the serene beaches and lush parks. Kenilworth offers delightful recreational areas and a vibrant shopping scene that cater to all ages. Its proximity to national and state parks provides ample opportunities for outdoor exploration, making this destination perfect for nature enthusiasts and families alike.

Things to do near Winnetka

Winnetka, Illinois, is perfect for outdoor family vacations, offering scenic views and various activities. Visitors can enjoy educational experiences, explore recreational areas, and attend music concerts. A must-visit spot is the Runnymede Recreation Center, which provides numerous opportunities for fun and relaxation. Whether you're looking to unwind or engage in community events, Winnetka has something for everyone.

Shopping

Schaefer's Wines and Liquors is a great spot just 3 miles away for unique gifts. If you're up for a drive, check out the Fashion Outlets of Chicago, 11 miles away, where you'll find a wide range of shops and entertainment options.

Recreation

Experience live music at Ravinia Pavilion, where the vibrant atmosphere enhances every concert. For sports enthusiasts, Ryan Field offers thrilling events in a lively setting. For a more relaxed vibe, visit Northbrook Sports Complex, perfect for unwinding and engaging in wellness activities.

Adventure

Rainbow Falls Waterpark, located 15 miles from Winnetka, offers thrilling water slides and relaxing pools, perfect for family fun and excitement. For nature lovers, the Salt Creek Trail, 20 miles away, provides scenic hiking with beautiful landscapes. Don't miss Jet Funn, 31 miles away, for exhilarating water sports adventures.

Nightlife

Experience the vibrant nightlife in Winnetka by visiting the North Shore Center for the Performing Arts for a captivating show, or head to the Rosemont Theatre for a romantic evening filled with culture. For some fun, check out Kiddie Kingdom, where adventure awaits just a short drive away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winnetka

To save money during your visit to Winnetka, plan your trip between December and February when hotel prices are lower, particularly on Wednesdays. Use Expedia to compare room rates and find the best deals; consider package deals to save on flights and activities as well. Joining Expedia's One Key membership can provide exclusive discounts and help you earn cash for future stays. Explore free local attractions and utilize public transport for affordable travel within the area, making your vacation enjoyable without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winnetka are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winnetka is Wednesday. The most expensive day to stay in Winnetka is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winnetka with flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Winnetka

Winnetka, Illinois, is a fantastic destination for outdoor and family vacations, offering beautiful beaches, urban parks, and modern college campuses. Visitors can immerse themselves in local culture while enjoying scenic views and family-friendly activities. With a variety of attractions, including serene waterfronts and vibrant parks, there's something for everyone to experience in this charming community.

  • Northwestern University: Located 5 miles from Winnetka, Northwestern University offers a vibrant atmosphere with its modern architecture and beautiful campus. Visitors can enjoy a stroll through its picturesque grounds and appreciate the rich history and academic excellence that permeates this esteemed institution.
  • Donald E. Stephens Convention Center: Situated 11 miles away, this event venue is a hub for business and conferences. The center boasts modern facilities and hosts a variety of events, making it an ideal stop for networking and exploring the latest in industry trends.
  • Chicago Botanic Garden: Just 4 miles from Winnetka, this stunning botanical garden provides a serene escape with its lush landscapes and romantic settings. Perfect for families, couples, or solo visitors, it's a place to relax and connect with nature.

Best time to go to Winnetka

The best time to visit Winnetka is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.8°F (-4.0°C)Light RainMostly CloudySlightly LowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnyAverageAverage
September66.7°F (19.3°C)Light RainMostly SunnyAverageSlightly High
October54.3°F (12.4°C)Light RainMostly SunnySlightly LowSlightly High
November41.5°F (5.3°C)Light RainMostly SunnyAverageAverage
December32.2°F (0.1°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winnetka

Traveling to Winnetka, Illinois, is convenient with access to three major airports. Chicago O'Hare International Airport (ORD) is the closest, located 13 miles away, with nearby hotels like the 4.5-star Loews Chicago O'Hare Hotel and the Hyatt Regency O'Hare Chicago, both about 2 miles from the airport. Chicago Midway International Airport (MDW) is 22 miles away, with luxurious options such as the 5-star Trump International Hotel & Tower Chicago, 9 miles from the airport. Milwaukee's General Mitchell International Airport (MKE) is 59 miles away, featuring hotels like the Pfister Hotel, 6 miles from the airport. Each airport offers various transportation services to make your arrival seamless.

Frequently asked questions

When is the best time to go to Winnetka?
The most popular time to visit Winnetka is during the summer months, particularly July, when the weather is warm and inviting. With average temperatures ranging from the mid-70s to low 80s Fahrenheit, this period is great for enjoying outdoor activities like strolling along the beach or exploring the charming downtown area.

During the peak season, which spans from June to August, Winnetka buzzes with visitors eager to take advantage of its picturesque parks and scenic waterfront. The vibrant atmosphere is complemented by various community events and festivals, making it a fantastic time for families and couples alike to immerse themselves in local culture and enjoy the lively ambiance.

For those who prefer a quieter experience, consider visiting in October. While the weather begins to cool, this month offers a beautiful backdrop of fall foliage and fewer crowds, allowing for a more relaxed exploration of the town's attractions. You can still enjoy the beautiful parks and take leisurely walks along the lakefront, all while indulging in the rich flavors of seasonal cuisine at local restaurants.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Winnetka hotel for you.
How can I save on a Winnetka hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winnetka hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winnetka hotel?
Prices for hotels in Winnetka often vary, but you can find a great deal from $56 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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