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19 Aug - 20 Aug
Tomorrow
20 Aug - 21 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

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Our top choices for Winnetka hotels

Breakfast included
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Pet-friendly
Reserve now, pay later
Pool

1. Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG
Prospect Heights
United States
Wynton
NZ$210
includes taxes & fees
23 Aug - 24 Aug
Holiday Inn Express & Suites Prospect Heights by IHG

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Dawn
NZ$399
includes taxes & fees
7 Sept - 8 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton

3. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
United States
Kristen
NZ$289
includes taxes & fees
30 Aug - 31 Aug
The Chicago Hotel Collection Ambassador Gold Coast

4. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Downtown Chicago
United States
Karaline
NZ$273
includes taxes & fees
30 Aug - 31 Aug
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

5. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
United States
Christina
NZ$210
includes taxes & fees
8 Sept - 9 Sept
Congress Plaza Hotel

6. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
United States
Christie
NZ$279
includes taxes & fees
7 Sept - 8 Sept
Claridge House Chicago, Tapestry Collection by Hilton

7. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Mexico
Mariana
NZ$292
includes taxes & fees
1 Sept - 2 Sept
Hilton Chicago/Magnificent Mile Suites

8. River Hotel

River Hotel
Downtown Chicago
United States
Sarah
NZ$276
includes taxes & fees
20 Aug - 21 Aug
River Hotel

9. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
Downtown Chicago
United States
Jerry
NZ$310
includes taxes & fees
7 Sept - 8 Sept
Aloft by Marriott Chicago Mag Mile

10. The Wade

The Wade
Downtown Chicago
United States
Georgia
NZ$342
includes taxes & fees
23 Aug - 24 Aug
The Wade

11. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
Downtown Chicago
United States
Richard
NZ$297
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Majestic Chicago Theatre District

12. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
Canada
James
NZ$284
includes taxes & fees
1 Sept - 2 Sept
FOUND Hotels, Chicago, Series by Marriott

13. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
Downtown Chicago
United States
Dawn
NZ$341
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Central Loop

14. Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Canada
Matthew
NZ$393
includes taxes & fees
31 Aug - 1 Sept
Hyatt Centric Chicago Magnificent Mile

15. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
United States
Janey
NZ$259
includes taxes & fees
30 Aug - 31 Aug
The Chicago Hotel Collection - Magnificent Mile

16. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
United States
Beth
NZ$339
includes taxes & fees
7 Sept - 8 Sept
Staypineapple, An Iconic Hotel, The Loop

17. citizenM Chicago Downtown

citizenM Chicago Downtown
Downtown Chicago
United States
lakadria
NZ$342
includes taxes & fees
7 Sept - 8 Sept
citizenM Chicago Downtown

18. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
United States
Steffany
NZ$325
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Chicago - Magnificent Mile

19. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Downtown Chicago
United States
Sally
NZ$308
includes taxes & fees
9 Sept - 10 Sept
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
United States
JENNIFER
NZ$372
includes taxes & fees
1 Sept - 2 Sept
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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Stay near popular Winnetka attractions

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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Elder Lane Beach

This lakefront sanctuary offers a serene escape with pristine sandy shores and Lake Michigan views. Enjoy a peaceful afternoon in the adjacent park with its well-maintained picnic areas and playground.
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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 theatre.

See all hotels in Winnetka
A suburban street with a stone house, a tree, and a clear sky.

Top Winnetka Hotel Reviews

Recent Reviews in Winnetka

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"This is a beautiful hotel and wonderful staff. We loved the design and the decor. The coffee area was so well set up and very thoughtful with honey, almond milk, lemons for water and tea. Very clean and delicious. The gym was a bit small but had all of the equipment and weights needed. They had chilled eucalyptus face towels that I loved so much at the end of my workout. The location was great. We loved the Nederlander theater and seeing The Notebook! My husband and I had an amazing time. Chicago was great! This hotel will not disappoint."
Amy 3-night trip
Posted 1 hour ago
The Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"We stayed at the Hyatt Regency Chicago, and when I tell you this hotel is HUGE, I mean HUGE! There are different towers, so it can take a minute to figure out where you’re going. Check-in is upstairs, not on the main level. The hotel has several restaurants, and I recommend making reservations, especially on busy weekends. We received a $25 nightly credit that could be used at participating restaurants during certain evening hours, but not at the Market. Our room was clean and comfortable. I stayed on the 20th floor with a beautiful river view. I could hear some music from the boats below, but it wasn’t loud enough to disturb my sleep. My mother was on the 30th floor and didn’t hear anything. Transportation is convenient with taxis outside, easy access to Ubers and a car rental location inside the hotel. There are also nice sitting areas with city views, charging stations and fireplaces. Everyone was nice, but Camille at the front desk was especially helpful and accommodating. I’m very particular about hotel cleanliness, and this room passed my cleanliness check! My only complaint was the bed, which was uncomfortable and sank in the middle. Overall, it’s pricey, but we enjoyed our stay. The location is a BIG plus, with Michigan Avenue, restaurants and attractions within walking distance."
Delvia 2-night trip
Posted 1 hour ago
Hyatt Regency Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent
"Clean rooms, very nice staff, and very close to Union Station. Walking distance to lots of places to eat. Felt safe and would recommend."
Donna 1-night trip
Posted 2 hours ago
Holiday Inn & Suites Chicago - Downtown by IHG
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

8/10 Good
"Great location. Room was clean although very humid. Loved the pool and ease of getting around. Elevators can take a bit longer."
Bobbie 3-night trip
Posted 2 hours ago
InterContinental Chicago Magnificent Mile by IHG
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"The breakfast is amazing!"
Claudia 2-night trip
Posted 2 hours ago
Hotel Riu Plaza Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"Great location. Helpful staff!"
Alesha 2-night trip
Posted 2 hours ago
Club Quarters Hotel, Central Loop, Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"This hotel is absolutely beautiful! And just across the street from the convention center! Our room was spotless, so clean and tidy. The restaurant serves an amazing breakfast buffet for under $30 per person.... well worth it for the variety and quality of the food. My only contention is that you have to pay for parking ($45 per night) which I've never ever heard of in the 50 years of my life. Apparently, most hotels in Chicago don't own their parking lots. They are owned by a separate company who collects their fees thru the hotel. For that reason alone I'm not sure i ever want to stay in Chicago again. I can find a million other places to visit that don't charge extra to park at the hotel. Otherwise, this hotel is very nice and clean and in an excellent location."
Nicholas 2-night trip
Posted 3 hours ago
Hyatt Regency O'Hare Chicago
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"The valets were very helpful in procuring my sister and I with taxis, Uber and Lyft services during our stay. All staff interactions were supremely pleasant. Our room was spotless."
Elizabeth 3-night trip
Posted 3 hours ago
Congress Plaza Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Free coffee Free printing Early check in fee available"
Sean 1-night trip
Posted 14 hours ago
Crowne Plaza Chicago West Loop by IHG

More cheap accommodation in Winnetka

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL
NZ$109
1 Sept - 2 Sept
includes taxes & fees
Motel 6 Elk Grove Village, IL - O'Hare
Motel 6 Schiller Park, IL - Chicago O'Hare

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL
NZ$112
8 Sept - 9 Sept
includes taxes & fees
Motel 6 Schiller Park, IL - Chicago O'Hare
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL
NZ$170
10 Sept - 11 Sept
includes taxes & fees
7.2/10 Good! (1,009 reviews)
Comfort Inn Chicago Schaumburg - O'Hare Airport
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL
NZ$246
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (2,782 reviews)
Travelodge by Wyndham Downtown Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL
NZ$308
7 Sept - 8 Sept
includes taxes & fees
Hampton Inn Chicago Downtown/Magnificent Mile
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

640 N Wabash Ave Chicago IL
NZ$310
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very good! (1,274 reviews)
Holiday Inn Express Chicago - Magnificent Mile by IHG

Find out more about Winnetka

Top reasons to visit Winnetka

  • Stunning Lake Michigan Shores: Enjoy scenic strolls along the picturesque shores of Lake Michigan, perfect for relaxation and outdoor fun.
  • Family-Friendly Activities: Engage in various sports, music concerts, and recreational activities suitable for all ages.
  • Charming Local Parks: Explore lush urban parks and dog parks, ideal for leisure and family outings.
  • Cultural Experiences: Immerse yourself in local events and vibrant performances that showcase Winnetka's community spirit.
  • Comfortable Accommodation: Choose from a range of welcoming hotels and guesthouses, ensuring a delightful stay for every traveller.

Find great hotels near Winnetka

Experience the charm of Winnetka, Illinois, with a variety of accommodation options designed to cater to every traveller. From well-equipped hotels to cozy guesthouses, you'll find pet-friendly and LGBTQIA welcoming spaces that ensure a delightful stay. Whether you're in town for business or leisure, the local hotels offer essential amenities and services, making your visit both comfortable and enjoyable. Explore the best of Winnetka with a stay that feels like home.

  • Holiday Inn Chicago North-Evanston by IHG: Situated 8.0km from Winnetka, the 3-star Holiday Inn Chicago North-Evanston offers a modern accommodation experience tailored for business travellers. With a commendable guest rating of 8.6 out of 10, this hotel features well-appointed rooms equipped with essential amenities to ensure a comfortable stay. Guests can take advantage of a business centre, meeting rooms, and complimentary Wi-Fi, making it an ideal hub for work-related travel. The hotel’s convenient location also provides easy access to nearby corporate offices and local attractions.
  • Motel 6 Prospect Heights, IL: Located 12.9km from Winnetka, the budget-friendly Motel 6 Prospect Heights offers a welcoming environment for travellers, especially those with pets. With a guest rating of 8.2 out of 10, this motel provides essential amenities at an affordable price. Pets are allowed onsite at no extra charge, making it a good choice for those wanting to bring their furry companions along. The straightforward accommodations focus on comfort and value, ensuring a hassle-free stay.
  • DoubleTree by Hilton Chicago - North Shore Conference Center: Just 6.4km from Winnetka, the 4-star DoubleTree by Hilton Chicago - North Shore Conference Center is an excellent choice for families and business travellers alike, boasting a guest rating of 8.8 out of 10. This hotel offers a range of amenities, including family-friendly services such as complimentary cribs for infants. Its prime location in the shopping district allows guests to explore vibrant retail options and dining experiences nearby, making it a multifaceted destination for leisure and work.

Where to stay in Winnetka

Winnetka, Illinois, offers a delightful blend of outdoor activities and family-friendly experiences. Stroll along the scenic shores of Lake Michigan, or explore the lush parks perfect for weekend getaways. For a taste of local charm, visit nearby towns with friendly vibes, ideal for romantic escapes or family outings. With its picturesque atmosphere and convenient campgrounds, Winnetka is the perfect base for your American adventure.

  • Chicago: Chicago is a vibrant metropolis that serves as a cultural hub in the United States. Located a short drive from Winnetka, it boasts a diverse array of attractions ideal for tourists. The city's visitor numbers peak during the warmer months from June to August, drawing families and outdoor enthusiasts alike. Chicago offers a plethora of experiences, from shopping in the Magnificent Mile to enjoying world-class theatre and sports events. Key landmarks include iconic urban parks and stadiums, making it a must-visit for anyone looking to immerse themselves in city life.
  • Northfield: Nestled close to Winnetka, Northfield is a charming village perfect for those seeking a more relaxed pace. While it attracts visitors throughout the year, the peak seasons are in April and the summer months of June to July. Northfield is ideal for families, offering educational opportunities, golf courses, and lively theatre performances. Local attractions include picturesque urban parks and a modern college university that add to the village's quaint charm. It’s a delightful spot to unwind while still being close to the excitement of the nearby city.
  • Kenilworth: Just 3.2km from Winnetka, Kenilworth is an upscale city known for its scenic beauty and family-friendly atmosphere. The city sees a moderate influx of tourists, particularly in March, May, and July. Visitors flock to Kenilworth for its outdoor recreational areas, educational institutions, and cultural offerings in the theatre scene. Notable highlights include beautiful beaches and a modern college university, providing ample opportunities for relaxation and exploration. Kenilworth is an excellent choice for those wanting to enjoy a quaint yet vibrant community close to the lakeshore.

Things to do in Winnetka

Shopping

Winnetka offers charming local shops along Elm Street, perfect for unique gifts and souvenirs. If you're up for a drive, visit Northbrook Court, about 16.1km away, featuring a mix of department stores, boutiques, and dining options in a spacious shopping environment.

Recreation

The Wellness House offers a peaceful environment with therapeutic workshops and holistic therapies tailored to individual needs. For relaxation, visit the nearby Skokie Lagoons, where you can enjoy tranquil walks, kayaking, and birdwatching amidst beautiful scenery, providing a rejuvenating escape from the hustle and bustle.

Adventure

Explore the stunning landscapes at the Skokie Lagoons, where you can enjoy kayaking and paddleboarding amidst lush greenery. For a thrill, visit the nearby North Shore Bike Path, offering picturesque routes for cycling enthusiasts eager to embrace the scenic beauty of the area.

Nightlife

Winnetka offers a relaxed nightlife with charming local bars and eateries. Enjoy a laid-back evening at the local pubs, where you can sample craft beers and delicious bites. For a more vibrant experience, nearby venues in neighbouring towns provide live music and dancing options to explore.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Winnetka

Winnetka is perfect for outdoor family holidays, offering stunning scenery and a variety of attractions. Visitors can enjoy the local beaches, urban parks, and dog parks, making it an ideal spot for both relaxation and recreation. The area's points of interest provide a blend of cultural experiences and family-friendly activities, ensuring a memorable vacation for all.

  • Clark Street Beach: Experience the relaxing beach vibes at Clark Street Beach, located 8.0km from Winnetka. Enjoy sunbathing, swimming, and taking in stunning views of Lake Michigan, making it a lovely spot for a leisurely day out.
  • Grosse Point Lighthouse: Situated 6.4km from Winnetka, the Grosse Point Lighthouse offers a glimpse into the area's rich maritime history. With its charming architecture and cultural significance, it's a wonderful place to explore and appreciate the local heritage.
  • Dawes Park: Just 8.0km away, Dawes Park is an urban oasis perfect for families. With ample green spaces for picnics and play, it’s an ideal spot to unwind and enjoy the outdoors in a vibrant city setting.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Getting to Winnetka, Illinois is convenient if you fly into one of its major airports. Chicago O'Hare International Airport (ORD) is situated 20.9km away, with excellent hotel options nearby including the 4.5-star Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare Chicago, both just 3.2km from the airport. Milwaukee General Mitchell International Airport (MKE) is 95.0km away, with nearby hotels like the 4.5-star Potawatomi Hotel & Casino. Chicago Midway International Airport (MDW) is 35.4km away, offering luxury stays such as the 5-star Trump International Hotel & Tower. Each airport provides accessible transport options from these hotels to ensure a smooth journey.

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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 hotel booking in Winnetka with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Winnetka hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Winnetka?
Prices for hotels in Winnetka often vary, but you can find a great deal from NZ$109 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 our cheapest rates.

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