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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, (2,406 reviews)
"Great spot and view, would stay again!"
United States
Kimberly
The price is CA $203
CA $285 total
includes taxes & fees
Mar 30 - Mar 31
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,704 reviews)
"Amazing place to stay!"
United States
Nia
The price is CA $179
CA $250 total
includes taxes & fees
Apr 1 - Apr 2
Hilton Chicago

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,032 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is CA $130
CA $152 total
includes taxes & fees
Mar 24 - Mar 25
River Hotel

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,802 reviews)
"Will stay here again! "
United States
Bryn
The price is CA $210
CA $247 total
includes taxes & fees
Mar 31 - Apr 1
L7 Chicago by LOTTE

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,110 reviews)
"Nice place to stay. "
United States
Akanksha
The price is CA $136
CA $192 total
includes taxes & fees
Mar 24 - Mar 25
The Godfrey Hotel Chicago

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, (1,320 reviews)
"Very beautiful place to stay"
United States
angie
The price is CA $171
CA $201 total
includes taxes & fees
Mar 24 - Mar 25
The Chicago Hotel Collection Ambassador Gold Coast

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,093 reviews)
"lovely hotel "
United States
alyvia
The price is CA $232
CA $321 total
includes taxes & fees
Mar 24 - Mar 25
Fairmont Chicago at Millennium Park

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,814 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is CA $96
CA $137 total
includes taxes & fees
Mar 25 - Mar 26
Freehand Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,150 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is CA $148
CA $174 total
includes taxes & fees
Mar 29 - Mar 30
Aloft Chicago Mag Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,178 reviews)
"Clean friendly staff love the decor "
United States
Kiasha
The price is CA $184
CA $216 total
includes taxes & fees
Apr 19 - Apr 20
Ivy Boutique Hotel

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,233 reviews)
"Excellent stay."
United States
Fenton
The price is CA $196
CA $279 total
includes taxes & fees
Mar 29 - Mar 30
Swissotel - Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,334 reviews)
"We had a great stay and the staff are very friendly and accommodating. "
United States
Krista
The price is CA $185
CA $251 total
includes taxes & fees
Apr 5 - Apr 6
Palmer House a Hilton Hotel

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,128 reviews)
"Great stay!"
United States
Hannah
The price is CA $130
CA $152 total
includes taxes & fees
Mar 24 - Mar 25
Club Quarters Hotel Wacker at Michigan, Chicago

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,753 reviews)
"Loved this hotel, i will be back"
United States
Shari
The price is CA $209
CA $245 total
includes taxes & fees
Mar 29 - Mar 30
The Wade

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,600 reviews)
"Great location ans staff was amazing!!"
United States
Bianca
The price is CA $189
CA $260 total
includes taxes & fees
Mar 29 - Mar 30
Hotel Riu Plaza Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,023 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is CA $184
CA $256 total
includes taxes & fees
Apr 6 - Apr 7
Staypineapple, An Iconic Hotel, The Loop

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,925 reviews)
"Hotel was really nice"
United States
LaCarr
The price is CA $156
CA $184 total
includes taxes & fees
Apr 5 - Apr 6
Hilton Garden Inn Chicago Downtown South Loop

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (509 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
The price is CA $122
CA $143 total
includes taxes & fees
Mar 24 - Mar 25
FOUND Hotel Chicago River North

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9,997 reviews)
"Clean room, nice hotel, nice staff"
United States
Melanie
The price is CA $143
CA $168 total
includes taxes & fees
Apr 1 - Apr 2
Congress Plaza Hotel

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,409 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is CA $129
CA $152 total
includes taxes & fees
Mar 24 - Mar 25
Club Quarters Hotel, Central Loop, Chicago
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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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

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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 $81 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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