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Our top choices for Winnetka hotels

1. Heart O' Chicago

Heart O' Chicago
2.0 star property
Edgewater
7.8 out of 10, Good, (1,001 reviews)
"It was exactly what we needed for an overnight stay. Everything very very clean, friendly front desk man, and cheaper than anywhere else by hundreds of dollars. If you just need to stay one night this place is perfect. Only a 10 minute uber to the Aargon Ballroom."
United States
Janelle
The price is CA $143
CA $167 total
includes taxes & fees
Dec 5 - Dec 6
Heart O' Chicago

2. Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (3,210 reviews)
"Great and helpful front desk staff and very accessible from the airport with free shuttle service"
United States
Nilantay Morshed
The price is CA $189
CA $218 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Chicago O'Hare – Rosemont by IHG

3. Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
"Everything was great and comfortable will stay again"
United States
Safrona
The price is CA $108
CA $170 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Chicago Downtown, Autograph Collection by Marriott

4. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,432 reviews)
"Convenient location near good restaurants."
United States
Scott
The price is CA $124
CA $188 total
includes taxes & fees
Nov 22 - Nov 23
Claridge House Chicago, Tapestry Collection by Hilton

5. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,577 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is CA $141
CA $168 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Chicago - Magnificent Mile

6. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,526 reviews)
"Enjoyed my stay will book again!"
United States
Jordan
The price is CA $151
CA $220 total
includes taxes & fees
Nov 27 - Nov 28
Hilton Chicago

7. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,308 reviews)
"Loved the continental breakfast and how close different bars and restaurants were at :)"
United States
Carole
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt House Chicago/West Loop-Fulton Market

8. 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, (2,765 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is CA $183
CA $266 total
includes taxes & fees
Nov 23 - Nov 24
Sable at Navy Pier Chicago, Curio Collection by Hilton

9. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.4 out of 10, Very good, (3,950 reviews)
"Friendly staff and great location"
United States
Alexis
The price is CA $119
CA $141 total
includes taxes & fees
Nov 23 - Nov 24
The Whitehall Hotel, BW Premier Collection

10. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,712 reviews)
"Great room - spacious, clean"
United States
Toninette
The price is CA $149
CA $177 total
includes taxes & fees
Nov 23 - Nov 24
Cambria Hotel Chicago Loop - Theatre District

11. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,957 reviews)
"Hotel is great for the price."
United States
alex
The price is CA $126
CA $150 total
includes taxes & fees
Dec 6 - Dec 7
ACME Hotel Chicago, Outset Collection by Hilton

12. Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4,524 reviews)
"We truly enjoyed our stay , the staff was friendly and welcoming"
United States
Malessa
The price is CA $124
CA $169 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Chicago Downtown/Magnificent Mile

13. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,566 reviews)
"Good location and nice hotel"
United States
Oleg
The price is CA $181
CA $264 total
includes taxes & fees
Nov 26 - Nov 27
Swissotel - Chicago

14. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,361 reviews)
"Great hotel"
United States
Kristopher Joel
The price is CA $162
CA $193 total
includes taxes & fees
Nov 23 - Nov 24
citizenM Chicago Downtown

15. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,590 reviews)
"Great hotel"
United States
Tracy
The price is CA $154
CA $183 total
includes taxes & fees
Nov 24 - Nov 25
Hampton Inn & Suites Chicago Downtown

16. Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Love this hotel! A great atmosphere! We love happy hour and the tacos!!"
United States
Lora
The price is CA $170
CA $202 total
includes taxes & fees
Nov 23 - Nov 24
Moxy Chicago Downtown

17. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,080 reviews)
"Great location Staff was terrific"
United States
Richard
The price is CA $154
CA $183 total
includes taxes & fees
Dec 6 - Dec 7
Courtyard by Marriott Chicago Magnificent Mile

18. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,312 reviews)
"Great location . Would definitely come back there"
United States
Kevin
The price is CA $157
CA $186 total
includes taxes & fees
Dec 6 - Dec 7
Aloft by Marriott Chicago Mag Mile

19. Hampton Inn Chicago Downtown/N Loop/Michigan Ave

Hampton Inn Chicago Downtown/N Loop/Michigan Ave
3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1,179 reviews)
"Great location and wonderful staff."
United States
Jodi
The price is CA $120
CA $164 total
includes taxes & fees
Dec 6 - Dec 7
Hampton Inn Chicago Downtown/N Loop/Michigan Ave

20. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,002 reviews)
"All the personal was very nice and helpful, the place is very clean and beautiful"
United States
Elizabeth
The price is CA $166
CA $198 total
includes taxes & fees
Dec 3 - Dec 4
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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.

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

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 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 $130 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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