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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, (2,482 reviews)
"Great place to stay "
United States
Mark
The price is CA $249
CA $343 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,033 reviews)
"It was great property, amazing location and the breakfast was fantastic. "
United States
Nichole
The price is CA $183
CA $256 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,141 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is CA $234
CA $327 total
includes taxes & fees
May 8 - May 9
Fairmont Chicago at Millennium Park

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,504 reviews)
"Clean, friendly, modern, overall great stay!!"
United States
Jennifer
The price is CA $298
CA $402 total
includes taxes & fees
May 25 - May 26
Hyatt Regency Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,134 reviews)
"Great stay"
United States
Matthew
The price is CA $170
CA $202 total
includes taxes & fees
May 8 - May 9
Congress Plaza Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,218 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is CA $181
CA $215 total
includes taxes & fees
May 10 - May 11
Aloft Chicago Mag Mile

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, (2,841 reviews)
"Great stay"
United States
Darin
The price is CA $193
CA $269 total
includes taxes & fees
May 10 - May 11
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,345 reviews)
"Great stay for a little weekend getaway.!"
United States
Jaylen
The price is CA $206
CA $245 total
includes taxes & fees
May 10 - May 11
Hilton Garden Inn Chicago Central Loop

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,001 reviews)
"Clean hotel great restaurant "
United States
ELIZABETH
The price is CA $186
CA $221 total
includes taxes & fees
May 10 - May 11
L7 Chicago by LOTTE

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,770 reviews)
"Clean room and great location "
United States
Diana
The price is CA $216
CA $297 total
includes taxes & fees
May 25 - May 26
Hilton Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,681 reviews)
"Loved staying at this hotel"
United States
Kimberly Marie
The price is CA $232
CA $315 total
includes taxes & fees
May 10 - May 11
LondonHouse Chicago, Curio Collection by Hilton

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, (1,402 reviews)
"Great stay, love the surrounding area. Rooms a bit small but overall a great stay. "
United States
Eric
The price is CA $196
CA $233 total
includes taxes & fees
May 10 - May 11
The Chicago Hotel Collection Ambassador Gold Coast

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, (2,445 reviews)
"Great place to stay."
United States
Yuge
The price is CA $200
CA $238 total
includes taxes & fees
May 10 - May 11
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,034 reviews)
"Great stay all around "
United States
Logan
The price is CA $270
CA $369 total
includes taxes & fees
May 26 - May 27
InterContinental Chicago Magnificent Mile by IHG

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,243 reviews)
"This was a great hotel. The staff and accommodations were terrific. I really enjoyed my stay "
United States
Alex
The price is CA $162
CA $234 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,499 reviews)
"Great hotel"
United States
Jalen
The price is CA $213
CA $287 total
includes taxes & fees
May 8 - May 9
Hyatt Centric The Loop Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,296 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is CA $269
CA $368 total
includes taxes & fees
May 27 - May 28
Swissotel - Chicago

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,156 reviews)
"Excellent location, very clean room and friendly staff"
United States
Alejandra
The price is CA $184
CA $218 total
includes taxes & fees
May 26 - May 27
River Hotel

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,102 reviews)
"Great breakfast and staff. "
United States
Kelly
The price is CA $219
CA $301 total
includes taxes & fees
May 25 - May 26
Arlo Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,247 reviews)
"Great place to stay , good location"
United States
Judith Daniella
The price is CA $188
CA $224 total
includes taxes & fees
May 10 - May 11
Hilton Chicago/Magnificent Mile Suites
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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.

Top Winnetka Hotel Reviews

Recent Reviews in Winnetka

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Hotels in Winnetka with star rating

Find out more about Winnetka

Top reasons to visit Winnetka

  • Stunning Beaches: Winnetka boasts beautiful beaches perfect for relaxation and family outings.
  • Outdoor Activities: The town offers numerous parks and recreational areas for hiking, picnicking, and enjoying nature.
  • Family-Friendly Atmosphere: Winnetka is known for its welcoming community, making it an ideal destination for families.
  • Scenic Views: Enjoy picturesque scenery and charming neighbourhoods, perfect for leisurely strolls.
  • Diverse Accommodations: A range of hotels and guesthouses cater to various needs, ensuring a comfortable stay.

Find great hotels near Winnetka

Discover the charm of Winnetka, Illinois, where a variety of accommodations await you. Whether you're seeking a business-friendly hotel, a pet-friendly guesthouse, or a welcoming inn for the LGBTQIA community, you'll find excellent options tailored to your needs. With a mix of comfort and convenience, Winnetka's best hotels provide the perfect base for your vacation adventures.

  • Holiday Inn Chicago North-Evanston by IHG: This 3-star hotel offers a welcoming environment for travellers seeking a business-oriented experience with an LGBTQIA-friendly atmosphere. Located 8.0km away from Winnetka, it is ideal for those attending conferences or requiring business amenities. Features include a fully accessible Business Centre, multiple meeting rooms, and dedicated Conference Space. Guests appreciate the modern decor and professional staff, making it a perfect choice for work and leisure combined.
  • DoubleTree by Hilton Chicago - North Shore Conference Center: With a 4-star rating, this hotel is located 6.4km from Winnetka and caters to families and pet owners. Known for its warm hospitality, highlighted by the signature DoubleTree cookie upon arrival, this hotel boasts a range of family-friendly amenities, including complimentary cribs. Being situated in a bustling shopping district adds convenience for those looking to explore local retailers. Pets are also welcome, with specific policies in place to ensure a comfortable stay for all guests.
  • Motel 6 Prospect Heights, IL: This pet-friendly motel, located 12.9km from Winnetka, offers a budget-conscious option for travellers. Known for its straightforward accommodations, Motel 6 is perfect for those with furry companions, as pets are permitted at no extra cost. Guests appreciate the clean, no-frills rooms and the welcoming policy for service animals. Ideal for a quick stay or a longer visit, this motel provides the essentials for a comfortable and convenient experience.

Where to stay in Winnetka

Winnetka, Illinois, offers a delightful blend of outdoor activities and picturesque scenery, perfect for family vacations. With its convenient location near the Wisconsin border, visitors can explore charming neighbourhoods and cities that embody a family-friendly atmosphere. Enjoy the fresh air and stunning city views while discovering romantic spots and friendly local vibes. Whether you're seeking relaxation or adventure, Winnetka and its surroundings promise an unforgettable experience.

  • Chicago: As a bustling metropolis, Chicago offers an array of experiences that cater to every type of traveller. Located a short distance from Winnetka, this vibrant city is renowned for its family-friendly activities, outdoor adventures, and rich urban culture. Peak visitor seasons from June to August bring crowds eager to explore the city's renowned shopping districts, entertainment arenas, and educational venues. Notable landmarks include iconic stadiums and a lively tourist precinct, making Chicago a must-visit for those looking to immerse themselves in a dynamic urban atmosphere.
  • Northfield: Just a stone's throw from Winnetka, Northfield is a charming village that attracts families and outdoor enthusiasts alike. With a steady flow of visitors peaking in April and during the summer months, this community offers a delightful blend of recreational areas and cultural experiences. Visitors can explore shopping areas and enjoy live music concerts, all while soaking up the village's welcoming atmosphere. Local highlights include sports facilities and urban parks, perfect for those seeking a leisurely day out in nature.
  • Kenilworth: Located merely 3.2km from Winnetka, Kenilworth is a picturesque city that captivates with its stunning scenery and family-friendly environment. The visitor experience peaks in March, May, and July, attracting those looking for outdoor activities and educational experiences. Kenilworth boasts beautiful beaches, including family-friendly options, alongside access to a national state park. This serene community is ideal for those wishing to relax while enjoying nature's beauty, making it a perfect addition to your travel itinerary.

Things to do near Winnetka

Winnetka, Illinois, is an excellent destination for outdoor enthusiasts and families alike, offering picturesque scenery and a variety of activities. Visitors can enjoy educational experiences, explore recreational areas, and attend lively music concerts, making it a well-rounded vacation spot for those seeking relaxation and entertainment in a charming setting.

Shopping

Schaefer's Wines and Liquors, just 4.8km away, offers a great selection for gifts. If you're up for a drive, check out the Fashion Outlets of Chicago, 17.7km away, for a variety of shops and entertainment options, or visit Wolff's Flea Market, also 17.7km away, for unique finds.

Recreation

Experience the Ravinia Pavilion for outdoor concerts that uplift your spirit, located 6.4km from Winnetka. For sports enthusiasts, Ryan Field offers exciting games, also 6.4km away. If you're seeking relaxation, visit the Northbrook Sports Complex, 9.7km away, for wellness and rejuvenation activities.

Adventure

Experience the thrills of Rainbow Falls Waterpark, located 24.1km from Winnetka, where you can enjoy exhilarating water slides and family-friendly attractions. For a scenic outdoor adventure, hike the Salt Creek Trail, 32.2km away, surrounded by stunning landscapes and vibrant nature.

Nightlife

Experience the vibrant nightlife in Winnetka by visiting the North Shore Center for the Performing Arts for captivating shows. For an exciting adventure, head to Kiddie Kingdom arcadeAdventureZone, or catch a romantic performance at the Rosemont Theatre, all within a short drive from the town.

*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, consider travelling between December and February, when accommodation prices are lower, particularly on Wednesdays. Avoid Saturdays for the best rates. Use Expedia to compare hotel prices, filter for Eco-certified options, and book packages that bundle flights and activities for additional savings. Take advantage of free local attractions and explore the area on foot, as Winnetka's charming streets are pedestrian-friendly. Public transport options are also available for economical travel around the town.

  • 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 refine your preferences, such as your budget, desired location, and the type of hotel you’re looking for. For instance, selecting the Eco-certified filter will showcase hotels that are sustainable and environmentally friendly, readily available for your stay. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winnetka with your flights and activities through an Expedia package.

Find the best attractions near Winnetka

Winnetka, Illinois, offers a delightful vacation experience for families and outdoor enthusiasts alike. With its beautiful beaches, urban parks, and nearby modern colleges, there’s something for everyone. Whether you're seeking cultural experiences or simply a relaxing day by the water, Winnetka’s attractions promise to create lasting memories for all visitors. Enjoy the scenic views and family-friendly activities that make this charming town a perfect getaway.

  • Northwestern University: Located 8.0km from Winnetka, Northwestern University boasts a vibrant campus atmosphere. Experience the blend of modern architecture and historic buildings, along with a lively student community that adds to the city's energy.
  • Donald E. Stephens Convention Center: Situated 17.7km away, this event venue is perfect for business travellers. Its expansive facilities host various events, offering a professional environment ideal for networking and collaboration.
  • Chicago Botanic Garden: Just 6.4km from Winnetka, this stunning botanical garden invites you to wander through beautifully landscaped gardens. Perfect for families and couples, it provides a serene escape with romantic spots and family-friendly activities.

Best time to go to Winnetka

The best time to visit Winnetka can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winnetka falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winnetka falls in January, 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

Winnetka, Illinois, is conveniently accessible via several major airports. Chicago O'Hare International Airport (ORD) is located 20.9km away, with nearby hotels like the 4.5-star Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare Chicago, both just 3.2km from the airport. Milwaukee's General Mitchell International Airport (MKE) is 95.0km away, offering options such as the 4.5-star Pfister Hotel. Lastly, Chicago Midway International Airport (MDW) is 23.2km from Winnetka, featuring luxurious hotels like the 5-star Trump International Hotel & Tower. Each of these airports provides various transportation services to ensure a smooth journey to your destination.

Frequently asked questions

What is the best area to stay in Winnetka?
The best area to stay in Winnetka is the village centre, particularly near Green Bay Road and Elm Street, for its convenience and access to local amenities.

This area is the heart of Winnetka, offering a pleasant and well-maintained environment. It's very walkable, with a selection of independent shops, cafes, and restaurants lining the main streets. The Winnetka Metra station is also located here, providing easy access to Chicago.

Couples looking for a relaxing getaway will appreciate this area. You'll find lovely boutiques for a leisurely browse and a variety of dining options for evenings out. The nearby Skokie Lagoons also offer opportunities for pleasant walks and kayaking.

For families, staying in the village centre provides great convenience. You're close to local parks, and the main street offers an ice cream parlour and casual eateries.
When is the best time to go to Winnetka?
The best time to go to Winnetka is during late spring (May to early June) or early autumn (September to October).

These periods offer the most pleasant weather for outdoor activities, with comfortable temperatures and less humidity than the peak summer months. You'll find the trees in full bloom in spring or showcasing beautiful colours in autumn, making for picturesque strolls along the lakefront or through the village's well-kept streets.

For those planning to enjoy the village's parks, golf courses, or the Winnetka Community House's events, these seasons provide ideal conditions without the larger crowds or higher temperatures of July and August.
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?
Members always get our best prices. Find our best Winnetka hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 CA $80 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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