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Our top choices for Winnetka hotels

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,821 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is CA $181
CA $263 total
includes taxes & fees
Jul 8 - Jul 9
Omni Chicago Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,159 reviews)
"Great stay!"
United States
Daniel
The price is CA $193
CA $229 total
includes taxes & fees
Jun 29 - Jun 30
Congress Plaza Hotel

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,457 reviews)
"Great stay!"
United States
Avradita
The price is CA $221
CA $263 total
includes taxes & fees
Jul 5 - Jul 6
Hilton Chicago/Magnificent Mile Suites

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,278 reviews)
"Would definitely stay there again"
United States
Benjy
The price is CA $185
CA $251 total
includes taxes & fees
Jul 1 - Jul 2
The Godfrey Hotel Chicago

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,608 reviews)
"Enjoyed our stay"
United States
keary
The price is CA $178
CA $211 total
includes taxes & fees
Jul 1 - Jul 2
The Chicago Hotel Collection - Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,668 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is CA $226
CA $269 total
includes taxes & fees
Jun 28 - Jun 29
Eurostars Magnificent Mile

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (646 reviews)
"Excellent stay in good location"
United States
Nicholas
The price is CA $171
CA $201 total
includes taxes & fees
Jun 28 - Jun 29
FOUND Hotel Chicago River North

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,412 reviews)
"The property was clean and the location was perfect!"
United States
Martha
The price is CA $203
CA $291 total
includes taxes & fees
Jul 1 - Jul 2
Swissotel - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,027 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is CA $184
CA $260 total
includes taxes & fees
Jul 6 - Jul 7
Warwick Allerton - Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (3,112 reviews)
"It was good place to stay for the Go Fest Event"
United States
Ken
The price is CA $162
CA $260 total
includes taxes & fees
Jul 5 - Jul 6
Freehand Chicago

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,414 reviews)
"The location is great and the rooms are comfortable and spacious. The free yoga classes were a nice bonus. It is clear that the hotel is going through a transition."
Canada
Caroline
The price is CA $262
CA $352 total
includes taxes & fees
Jul 1 - Jul 2
Sports Illustrated Resorts Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,450 reviews)
"Staff was great."
United States
Marianne
The price is CA $315
CA $425 total
includes taxes & fees
Jul 6 - Jul 7
Hyatt Regency Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,494 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is CA $317
CA $419 total
includes taxes & fees
Jun 30 - Jul 1
Palmer House a Hilton Hotel

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,263 reviews)
"Wonderful stay"
United States
Taylor
The price is CA $173
CA $249 total
includes taxes & fees
Jul 5 - Jul 6
Silversmith Hotel Chicago Downtown

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,108 reviews)
The price is CA $225
CA $309 total
includes taxes & fees
Jul 1 - Jul 2
Staypineapple, An Iconic Hotel, The Loop

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,755 reviews)
The price is CA $335
CA $440 total
includes taxes & fees
Jul 6 - Jul 7
LondonHouse Chicago, Curio Collection by Hilton

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,251 reviews)
"Excellent place to stay, as we found it central & walkable to most parks & attractions. The place was spotless & the staff were fantastic."
Canada
Jody
The price is CA $198
CA $236 total
includes taxes & fees
Jul 1 - Jul 2
River Hotel

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,578 reviews)
"Great stay"
United States
Matt
The price is CA $200
CA $279 total
includes taxes & fees
Jul 1 - Jul 2
Hotel 55 Chicago Downtown

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, (1,628 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is CA $174
CA $207 total
includes taxes & fees
Jun 29 - Jun 30
The Chicago Hotel Collection Ambassador Gold Coast

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,186 reviews)
"Great hotel with awesome location"
United States
Daniel
The price is CA $187
CA $222 total
includes taxes & fees
Jul 1 - Jul 2
Central Loop 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 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

More cheap stays in Winnetka

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 $90 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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