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Find hotels in Winnetka, IL from $100

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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

    The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

    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 rooftop terrace with outdoor seating, a view of the city skyline, and a building with a brick facade.

    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 hotel lobby with seating areas, a large cityscape painting, and a patterned carpet.

    8. River Hotel

    A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

    9. Renaissance Chicago North Shore Hotel

    An outdoor seating area with wicker chairs and a sofa, surrounded by trees and a building facade.

    10. Sheraton Chicago Northbrook Hotel

    A modern hotel lobby with a central seating area, multiple dining tables, and a decorative plant wall.

    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 multi-story hotel with a flat facade, multiple windows, and a sign indicating it is a Marriott Residence Inn.

    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 person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

    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

    A rooftop lounge with outdoor seating, a fire feature, and transparent dome structures.

    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 spacious bar area with high ceilings and large windows, offering views of a cityscape.

    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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    The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

    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 rooftop terrace with outdoor seating, a view of the city skyline, and a building with a brick facade.

    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 reviews8.8Excellent1,000 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 22 - Nov 23Total 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.

    View properties in map for Northfield

    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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    View properties in map for Gross Point

    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

    Winnetka, a charming destination, offers a perfect blend of outdoor activities and family-friendly experiences. Explore the scenic beaches and urban parks, or venture to the nearby Winnetka Indian Hill Station for unique adventures. This picturesque locale is ideal for travelers seeking culture and stunning scenery.

    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

    Holiday Inn Chicago O'Hare – Rosemont by IHG

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

    L7 CHICAGO by LOTTE HOTELS

    A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

    Hilton Vacation Club Hotel Blake Chicago

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

    Hyatt Regency Chicago

    A spacious bar area with high ceilings and large windows, offering views of a cityscape.

    LondonHouse Chicago, Curio Collection by Hilton

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

    Hyatt Place Chicago/River North

    A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

    Hotel Riu Plaza Chicago

    The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

    citizenM Chicago Downtown

    A modern building with a colorful facade and a red circular seating area.

    Hilton Chicago/Magnificent Mile Suites

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

    Courtyard by Marriott Chicago Magnificent Mile

    A hotel room with a large window offering a city view, a bed, a desk, and a chair.

    Springhill Suites by Marriott Chicago Downtown/ River North

    A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

    Hampton Inn & Suites Chicago Downtown

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

    Hotel 505 River North

    A modern restaurant interior with a green wall, hanging lights, and a long dining area.

    Fairfield Inn & Suites Chicago Downtown/River North

    A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

    The Royal Sonesta Chicago Downtown

    A dining area with a table set for four, large windows offering a cityscape view at dusk.

    InterContinental Chicago Magnificent Mile by IHG

    The Intercontinental hotel facade with a large American flag and a floral display.

    Swissotel - Chicago

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

    Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

    A building with a brick facade, a flagpole with an American flag, and a sign for 'Fairfield by Marriott.'

    Sable at Navy Pier Chicago, Curio Collection by Hilton

    An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

    Residence Inn Chicago Downtown Magnificent Mile

    A modern hotel lobby with a spiral staircase, seating areas, and large windows offering city views.

    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.

    Frequently Asked Questions

    What is the best area to stay in Winnetka?

    The best area to stay in Winnetka is near the village center, particularly along Green Bay Road and Elm Street, as this offers convenient access to local amenities and the Metra train station.

    This central area provides a pleasant, walkable experience with a selection of boutique shops, local eateries, and essential services. The Winnetka Metra station is located here, offering direct train service to downtown Chicago, making it very convenient for those who wish to explore the city without driving.

    Couples looking for a relaxing stay will appreciate the village center's peaceful atmosphere and access to nearby parks like Indian Hill Park. The area's well-maintained streets and local businesses create a comfortable setting for a quiet getaway.

    For solo travelers, staying near the village center offers excellent connectivity.

    When is the best time to go to Winnetka?

    The best time to visit Winnetka is during the late spring (May to early June) and early fall (September to October) when the weather is pleasant and the natural beauty of the area is at its peak.

    During these months, you'll experience comfortable temperatures, ideal for enjoying outdoor activities such as walking along the Lake Michigan shoreline or exploring the village's well-maintained parks. The trees are either in full bloom or displaying vibrant autumn colors, enhancing the scenic quality of the area. This period also avoids the peak summer crowds and the colder winter months.

    Families will find late spring particularly appealing, as the weather is mild enough for children to play outdoors without extreme heat, and local events like farmers' markets may begin. Many of the community's public spaces, like the Hubbard Woods Park, are great for picnics and casual strolls when the weather is agreeable.

    Couples looking for a relaxing getaway will appreciate the early fall. The cooler air and colorful foliage create a picturesque setting for leisurely walks through residential areas with their stately homes and along the quiet beaches.

    Can I cancel my hotel reservation on Expedia?

    You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winnetka.

    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 $100 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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