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Go beyond your typical stay in Winnetka

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Check prices for these dates, December 13 – 14, 2026

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Our top choices for Winnetka hotels

1. Kasa Magnificent Mile Chicago

A balcony with a table and chairs, a bottle of wine, and a glass of wine.

2. Hotel Riu Plaza Chicago

A high-rise building with a modern architectural design, featuring a grid-like facade and large windows.

3. DoubleTree by Hilton Chicago - North Shore Conference Center

A bar area with wooden flooring, bar stools, and a counter with various bottles. There are framed pictures on the walls and a menu board.

4. Congress Plaza Hotel

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

5. The Chicago Hotel Collection Ambassador Gold Coast

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

6. Hilton Garden Inn Chicago North Shore/Evanston

A spacious lobby with a modern design, featuring large potted plants and a series of unique, white pendant lights.

7. Hampton Inn & Suites Chicago-North Shore/Skokie

A modern kitchen with wooden cabinets, a black refrigerator, a microwave, and a dishwasher.

8. River Hotel

A grand lobby with a marble staircase, plush seating, and a large painting on the wall.

9. Renaissance Chicago North Shore Hotel

A hotel entrance with a prominent 'Renaissance' sign, modern architecture, and a clear sky.

10. Sheraton Chicago Northbrook Hotel

A spacious hotel lobby with multiple seating areas, a bar, and a kitchen visible in the background.

11. Hilton Orrington / Evanston

An outdoor dining area with wicker chairs and tables, overhead lighting, and a view of the street.

12. Hilton Chicago/Magnificent Mile Suites

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

13. Residence Inn by Marriott Chicago Wilmette/Skokie

A modern hotel lobby with a fireplace, seating areas, and large windows.

14. Eurostars Magnificent Mile

A room with two chairs and a small table, a large window with a city view at night.

15. The Glen Club

A golf course with a pond reflecting the surroundings, a brick building with multiple windows, and trees around the area.

16. L7 CHICAGO by LOTTE HOTELS

A bar area with a long counter, multiple stools, and shelves stocked with bottles.

17. Staybridge Suites Chicago - Glenview by IHG

A hotel entrance with a covered patio, stone walls, and outdoor seating.

18. The Chicago Hotel Collection - Magnificent Mile

An outdoor seating area with a fire feature, wicker furniture, and a view of the city skyline at night.

19. Hyatt Regency Deerfield

A spacious lobby with a central seating area, a piano, and a large window overlooking a garden.

20. Hyatt Regency Chicago

A bar with a circular liquor display, seating with stools, and a city view through large windows.

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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A high-rise building with a modern architectural design, featuring a grid-like facade and large windows.

Hotel Riu Plaza Chicago

Downtown Chicago View

A bar area with wooden flooring, bar stools, and a counter with various bottles. There are framed pictures on the walls and a menu board.

DoubleTree by Hilton Chicago - North Shore Conference Center

Skokie View

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

Congress Plaza Hotel

Downtown Chicago View

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago View

A spacious lobby with a modern design, featuring large potted plants and a series of unique, white pendant lights.

Hilton Garden Inn Chicago North Shore/Evanston

Downtown Evanston View
9.4Exceptional5,699 reviews8.6Excellent1,184 reviews8.0Very good10,071 reviews8.0Very good2,702 reviews8.8Excellent1,012 reviews
$146 nightly $174 total Dec 14 - Dec 15Total with taxes and fees$118 nightly $135 total Dec 6 - Dec 7Total with taxes and fees$107 nightly $127 total Nov 23 - Nov 24Total with taxes and fees$116 nightly $138 total Nov 15 - Nov 16Total with taxes and fees$114 nightly $130 total Dec 6 - Dec 7Total with taxes and fees
  • Breakfast included
  • Pool
  • Spa
  • Pet friendly
  • WiFi included
  • Parking
  • Breakfast included
  • Pool
  • Spa
  • Pet friendly
  • WiFi included
  • Parking
  • Breakfast included
  • Pool
  • Spa
  • Pet friendly
  • WiFi included
  • Parking
  • Breakfast included
  • Pool
  • Spa
  • Pet friendly
  • WiFi included
  • Parking
  • Breakfast included
  • Pool
  • Spa
  • Pet friendly
  • WiFi included
  • Parking

Where to stay in Winnetka

Winnetka offers a delightful blend of family-friendly outdoor activities and scenic charm. Explore the vibrant Winnetka Center and nearby districts for a great stay. For your next trip, enjoy the welcoming atmosphere, perfect for relaxation or urban adventures in the nearby Central Loop.

A river with a yellow boat, surrounded by tall buildings and a bridge.

A cityscape with a prominent bridge over a river, tall buildings, and an American flag.

A coastal cityscape with a prominent skyscraper, a beach, and a clear sky.

A bronze lion statue in front of a classical building with steps leading up to it.

A city skyline at sunset with a prominent bridge and a river reflecting the buildings.

View properties in map for Chicago (and vicinity)

Chicago

Discover Chicago, a vibrant metropolis perfect for travelers seeking a blend of urban excitement and cultural experiences. Visitors will enjoy the bustling shopping along Michigan Avenue, the entertainment at Navy Pier, and the events held at McCormick Place. Situated in Chicago, Winnetka offers easy access to these attractions, making it an ideal base for exploring the city. With its rich offerings, Chicago is a smart choice for your hotel stay, ensuring a memorable vacation.

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An aerial view of a suburban area with a large parking lot, residential houses, and a mix of deciduous trees.

A field of yellow flowers with green foliage and trees in the background under a blue sky.

An aerial view of a residential neighborhood with houses, roads, and trees.

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Northfield

Experience the charm of Northfield, an excellent hub for travelers seeking a blend of business and leisure. This welcoming village in Winnetka is perfect for those wanting to explore attractions like Northwestern University, the stunning Chicago Botanic Garden, and the Donald E. Stephens Convention Center. With its appealing parks and sports facilities, Northfield is ideal for families and outdoor enthusiasts alike. Its strategic location makes booking your stay here a smart choice for an enriching getaway.

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A wooden dock extending into a calm body of water, with boats docked nearby and a building with a red roof in the background.

A coastal beach with a lighthouse, pier, and grassy dunes.

A waterfront with boats docked, a bridge, and buildings with balconies.

A river with a boat carrying passengers, surrounded by tall buildings and a bridge.

View properties in map for Kenilworth

Kenilworth

Make your vacation planning effortless by staying in Kenilworth, a haven for families and couples due to its proximity to beautiful beaches and the scenic Northwestern University. Visitors will enjoy exploring the vibrant local theater scene and the peaceful Baha'i House of Worship, perfect for a leisurely day. With its charm and community feel, Kenilworth, located about 2 miles from Winnetka, is an ideal choice for a memorable getaway.

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A serene landscape with a pond, manicured grass, and a variety of trees.

A serene lake surrounded by lush greenery and trees.

A sunset over a beach with a fence in the foreground.

Photo by WanderingFunk009

A wooden structure in the ocean with a tall, weathered post in the foreground.

Photo by Monica Ferro

A sandy beach with people relaxing, a sailboat, and houses in the background.

View properties in map for Glencoe

Glencoe

Ideally situated for families and weekend travelers, Glencoe offers a delightful escape just about 2 miles from Winnetka. Visitors can explore the beautiful Chicago Botanic Garden, enjoy the local beach, or attend events at the Donald E. Stephens Convention Center. With its scenic outdoor experiences and vibrant cultural attractions, Glencoe is a smart choice for those looking to relax and recharge.

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Gross Point

Travelers visiting the area often choose Gross Point, especially couples and families seeking a blend of outdoor and city experiences. This charming neighborhood offers easy access to attractions like Northwestern University, the Baha'i House of Worship, and the Donald E. Stephens Convention Center, ensuring a rich mix of education, culture, and leisure. Located about 2 miles from Winnetka, Gross Point is a smart choice for those looking to explore the best of Wilmette while enjoying a relaxing stay.

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Stay near popular Winnetka attractions

A modern architectural building with reflective glass surfaces and a concrete base.

Northwestern University

Rating: 8.8/10 (2,121 reviews)

Set the stage for your visit to Northwestern University, a vibrant hub of education and culture located in Evanston, Illinois. With its dynamic atmosphere and stunning campus, this modern university offers unique events and attractions year-round. It's about a 5-mile drive from Winnetka, making it a convenient stop during your trip.

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An aerial view of a university campus with historic buildings, a large modern library, and a waterfront.

Loyola University Chicago

Rating: 8.2/10 (300 reviews)

Often cited as a favorite among prospective students and visitors alike, Loyola University Chicago offers a vibrant campus atmosphere filled with city vibes. Located about 8 miles by car from Winnetka, it’s an easily accessible destination, making it a convenient stop for those exploring the area.

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A traditional Japanese building with a thatched roof, situated by a calm river with rocks and lush greenery.

Photo by Monica Ferro

Chicago Botanic Garden

Rating: 8.8/10 (46 reviews)

No trip is complete without a visit to the Chicago Botanic Garden, a stunning oasis ideal for families and couples alike. Nestled in Northbrook, this beautiful garden offers diverse landscapes and vibrant plant collections. It's about 4 miles from Winnetka, making it a convenient escape for a refreshing day outdoors.

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A large white building with a dome, surrounded by trees and grass.

Baha'i House of Worship

Rating: 8.0/10 (5 reviews)

An essential stop for spiritual seekers and culture enthusiasts, the Baha'i House of Worship offers a serene environment for reflection and appreciation of diverse beliefs. Nestled about 4 miles from Winnetka, this stunning temple showcases intricate architecture, making it a unique addition to your travel itinerary while providing easy access to nearby attractions.

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A box of assorted chocolates.

Winnetka

Perfectly suited for chocolate lovers, Chocolate Box in Winnetka offers a delightful array of handmade confections and artisan treats. Nestled in the heart of the village, it's easily accessible and allows visitors to indulge in a sweet experience. Staying nearby makes it simple to enjoy this local favorite.

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Donald E. Stephens Convention Center

Rating: 8.6/10 (873 reviews)

Ideal for travelers interested in vibrant events, the Donald E. Stephens Convention Center in Rosemont offers a dynamic venue for conferences and exhibitions. Located about 13 miles by car from Winnetka, it provides easy access for those seeking to explore a hub of business activity and networking opportunities. Staying nearby enhances your experience with convenient event access.

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Elder Lane Beach

Enjoy the simplicity of Elder Lane Beach, a charming spot perfect for families and beach lovers. Experience its delightful beach vibes as you relax by the water. Conveniently located within Winnetka, this beach offers easy access to local attractions, making it a great base for your visit.

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Copernicus Center

A stellar choice for business travelers, Copernicus Center offers a dynamic venue for events and conferences in Chicago. Located about 10 miles from Winnetka, it provides a professional atmosphere while being easily accessible, making it a practical option for those seeking to combine work and leisure.

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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.

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A suburban street with a stone house, a tree, and a clear sky.

Top Winnetka Hotel Reviews

Sable at Navy Pier Chicago, Curio Collection by Hilton

A modern bathroom with a large mirror, a sink, and a towel rack.

Hilton Vacation Club Hotel Blake Chicago

A hotel entrance with a prominent 'MORTON' sign, a 'HOTEL BLAKE CHICAGO' sign, and a '542' address number.

ACME Hotel Chicago, Outset Collection by Hilton

A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

Claridge House Chicago, Tapestry Collection by Hilton

A bar area with a long counter, multiple stools, and a modern chandelier.

L7 CHICAGO by LOTTE HOTELS

A bar area with a long counter, multiple stools, and shelves stocked with bottles.

citizenM Chicago Downtown

A tall, modern skyscraper with a glass facade, surrounded by other high-rise buildings.

Hilton Chicago/Magnificent Mile Suites

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

LondonHouse Chicago, Curio Collection by Hilton

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

Moxy Chicago Downtown

A modern lounge area with seating, a coffee table, and a view of the city at night.

Holiday Inn Chicago O'Hare – Rosemont by IHG

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

Hyatt Regency Chicago

A bar with a circular liquor display, seating with stools, and a city view through large windows.

DoubleTree by Hilton Chicago - Magnificent Mile

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

Sports Illustrated Resorts Chicago

A hotel bathroom with a large mirror, a sink, and a vanity.

Hampton Inn & Suites Chicago Downtown

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

Arlo Chicago

The entrance to Arlo Chicago with a clear sign displaying the address 168 N Michigan.

Swissotel - Chicago

A dining table set for six with a cityscape view through large windows.

Residence Inn Chicago Downtown Magnificent Mile

Lobby lounge

Hyatt House Chicago/West Loop-Fulton Market

A modern lounge area with seating, a bar, and large windows offering views.

Fairfield Inn & Suites Chicago Downtown/River North

A hotel entrance with a sign for Fairfield Inn & Suites by Marriott.

Le Méridien Essex Chicago

A modern living room with a sofa, armchairs, and a coffee table. There are bookshelves and a decorative wall panel.

Find out more about Winnetka

Top reasons to visit Winnetka

Find great hotels near Winnetka

Discover a variety of hotel accommodations in Winnetka, Illinois, catering to both leisure and business travelers. From pet-friendly options to LGBTQIA welcoming environments, you’ll find the best hotels that suit your needs. Whether you're looking for hotels near Winnetka or the most popular spots to stay, Winnetka offers a welcoming atmosphere and convenient amenities for a memorable vacation experience.

Where to stay in Winnetka

Winnetka, Illinois, offers a delightful blend of outdoor activities and family-friendly experiences, making it an ideal vacation spot. Explore nearby charming neighborhoods and cities to enjoy a warm, inviting atmosphere filled with friendly locals and romantic spots. With its scenic parks and vibrant community, Winnetka is perfect for those seeking relaxation and adventure. Don't miss trending attractions within a short drive, ensuring a memorable getaway for travelers of all kinds.

Things to do near Winnetka

Winnetka, Illinois, offers a delightful blend of outdoor activities and family-friendly attractions. Visitors can explore picturesque parks, enjoy scenic hiking trails, and attend local music concerts. Whether you're seeking a romantic evening or want to engage in educational experiences, Winnetka has something for everyone. Don't miss the chance to immerse yourself in the area's charming amenities and vibrant recreational areas.

Shopping

The charming boutiques in downtown Winnetka, like The Book Stall and The Spice House, offer unique gifts and local products. If you're up for a drive, Northbrook Court and Old Orchard Mall are great options, featuring a variety of national retailers and dining experiences to explore.

Recreation

At Chevy Chase Country Club, indulge in upscale amenities and serene golf courses, perfect for relaxation. Ravinia Green Country Club offers a luxurious atmosphere with exquisite dining and wellness programs. Bridges of Poplar Creek Country Club invites you to unwind amidst beautiful landscapes and top-notch facilities for rejuvenation.

Adventure

Winnetka is home to the beautiful beaches along Lake Michigan, perfect for swimming, kayaking, or sunbathing. For hiking enthusiasts, the nearby Skokie Lagoons offers scenic trails and wildlife spotting. Don't miss the exhilarating bike paths along the lakefront for stunning views and fresh air.

Nightlife

Explore the vibrant nightlife at The Lantern, a cozy spot on Elm Street with craft cocktails and a welcoming atmosphere. For a lively evening, visit the Winnetka Sports Bar on Green Bay Road, where you can enjoy pub fare while catching a game on the big screen.

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

Booking tips and Expedia advantages for Winnetka

Find the best attractions in and around Winnetka

Winnetka, Illinois, is perfect for outdoor and family vacations, offering beautiful scenery and a variety of attractions. Visitors can enjoy the local beaches, urban parks, and museums that cater to those seeking cultural experiences and outdoor fun. Whether you're relaxing by the water or exploring the rich history, Winnetka provides a delightful getaway for travelers looking to connect with nature and the community.

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.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
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 three major airports nearby. Chicago O'Hare International Airport (ORD) is situated 13 miles away, with excellent hotel options like the 4.5-star Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare Chicago, both 2 miles from the airport. Milwaukee General Mitchell International Airport (MKE) is 59 miles away, featuring hotels such as The Pfister Hotel and Kimpton Journeyman Hotel, each 6 miles from the airport. Lastly, Chicago Midway International Airport (MDW) is 22 miles away, with luxury stays like The Langham and Trump International Hotel, both 9 miles from MDW. Each airport offers accessible transportation to these hotels.

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