Book Hotels in Winnetka, IL

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Top Winnetka hotels

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $204 total per night from Nov 3 to Nov 4
$204 total
per night
Nov 3 - Nov 4
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"This hotel is right off of Michigan Ave with many restaurants, stores, and museums. Excellent location."

Reviewed on Sep 30, 2025

Opens in a new windowcitizenM Chicago Downtown
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is $324 total per night from Nov 2 to Nov 3
$324 total
per night
Nov 2 - Nov 3
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a ...
"Great Location."

Reviewed on Oct 6, 2025

Opens in a new windowInterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $170 total per night from Nov 3 to Nov 4
$170 total
per night
Nov 3 - Nov 4
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference ...
"Our stay was great"

Reviewed on Oct 6, 2025

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $199 total per night from Nov 5 to Nov 6
$199 total
per night
Nov 5 - Nov 6
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and ...
"Everything was perfect"

Reviewed on Oct 5, 2025

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $206 total per night from Oct 20 to Oct 21
$206 total
per night
Oct 20 - Oct 21
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge ...
"Rooms are clean, public transportation is close by and there is a lot of walkable food options."

Reviewed on Oct 6, 2025

Opens in a new windowHilton Garden Inn Chicago Downtown/Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $229 total per night from Oct 30 to Oct 31
$229 total
per night
Oct 30 - Oct 31
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express ...
"The hotel lobby is incredible including a number of shops and bars plus live music. Our room had a handicap accessible shower which caused water to get all over the entire bathroom floor. Other than that, it was a great experience."

Reviewed on Oct 3, 2025

Opens in a new windowPalmer House a Hilton Hotel
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $133 total per night from Nov 3 to Nov 4
$133 total
per night
Nov 3 - Nov 4
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. WiFi in public areas is free.
"We chose this hotel due to location, and previous stays there."

Reviewed on Oct 2, 2025

Opens in a new windowWarwick Allerton - Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $170 total per night from Nov 2 to Nov 3
$170 total
per night
Nov 2 - Nov 3
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center ...
"Multiple shopping options"

Reviewed on Oct 3, 2025

Opens in a new windowCongress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $113 total per night from Nov 4 to Nov 5
$113 total
per night
Nov 4 - Nov 5
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also ...
Good for 3 nights
"The price was right, the location excellent for shopping, riverwalk, other attractions within walking distance. The rooms are tiny, the bar and breakfast inconsistent. The mattress was terrible and needs to be replaced. The lobby area is beautifully refurbished and a place to spend time reading, ..."

Reviewed on Sep 30, 2025

Opens in a new windowFreehand Chicago
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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.

Winnetka Hotel & Travel Guide

If you're thinking of discovering the local culture of the Chicago region and need Winnetka hotels, you'll have a wonderful list to select from. Enjoy reading the 24 room choices on Travelocity, which are all within a 6-mile (10-kilometer) radius of the city center.

Travelocity-listed accommodation options that are close to the heart of Winnetka include the Hampton Inn & Suites Chicago-North Shore/Skokie and Renaissance Chicago North Shore Hotel.

The Chicago Downtown Condo - Michigan Ave Suite ID #14-15 is around 18 miles (28 kilometers) outside the town center of Winnetka. An alternative accommodation option is the The Peninsula Chicago, which is positioned 16 miles (25 kilometers) away. The Waldorf Astoria Chicago as well as the Trump International Hotel & Tower Chicago are some other accommodation options worth checking out around Winnetka.

Looking for more activities? Spend some time checking out Woodfield Mall and Legoland Discovery Center, in Schaumburg, 16 miles (26 kilometers) west of Winnetka. The Renaissance Schaumburg Convention Center Hotel and Residence Inn by Marriott Chicago Schaumburg/Woodfield Mall are some of the Travelocity-recommended short and long-stay options in Schaumburg. For another option, head to Algonquin, 30 miles (46 kilometers) west of Winnetka, where you have the options of the Holiday Inn Express Hotel & Suites Chicago-Algonquin and Victorian Rose Garden. While visiting Algonquin, set aside some time to explore the Terrace Hill Golf Course and Raging Buffalo Snowboard Ski Park.

Before your Winnetka trip comes to an end, why not spend an hour or two enjoying the spectacle with Chicago supporters at a community game. Wrigley Field is located 12 miles (19 kilometers) to the southeast of Winnetka. Stay in the middle of the action at the Roscoe Village Guesthouse or the Best Western Plus Hawthorne Terrace Hotel.

If you are traveling through O'Hare International Airport and are hoping to book a room in the area, why not consider Loews Chicago O'Hare Hotel or The Westin O'Hare.

Top reasons for your vacation to Winnetka

  • Scenic Lakefront: Take a stroll along Winnetka's beautiful lakefront, where you can enjoy stunning views and a refreshing breeze.
  • Nature Trails: Explore the forests and nature trails surrounding Winnetka, perfect for hiking and birdwatching.
  • Baseball: Catch a baseball game and experience the excitement of America's favorite pastime in Winnetka.
  • Shopping: Enjoy a leisurely day of shopping in Winnetka's charming boutiques and stores.
  • Dining: Indulge in delicious dining options, with a variety of restaurants offering diverse cuisines.

Find your favorite hotels in Winnetka

If you're planning a family outdoor vacation in Winnetka, Illinois, you'll find a range of hotel accommodations to suit your needs. From cozy bed and breakfasts to modern hotels, there are options for every budget. Whether you're looking for a 5-star luxury experience or a comfortable stay near outdoor attractions, you'll find top hotels in and around Winnetka. These accommodations provide a great base for exploring the beautiful outdoor scenery and enjoying all that this charming area has to offer.

Hotel nameTypeStarsDescription
River HotelHotel4.0This 4.0-star rated hotel offers a convenient location with close proximity to the river, theater, breathtaking views, friendly locals, shopping centers, entertainment options, historic monuments, walking trails, and museums. It also provides a concierge service. The River Hotel is located 16.2 miles away from Winnetka, making it a great option for your outdoor vacation.
Congress Plaza HotelHotel3.5With a 3.5-star rating, this hotel is located near stunning views, theaters, a university, shopping areas, a beautiful lake, friendly locals, historical sites, walking paths, museums, and even windsurfing spots. It is situated 17.1 miles away from Winnetka, making it a convenient choice for your outdoor getaway.
Eurostars Magnificent MileHotel4.0This 4.0-star rated hotel is known for its close proximity to theaters, captivating views, friendly locals, trendy boutiques, shopping venues, museums, segway tours, historic monuments, and even a steam room. Located just 15.8 miles away from Winnetka, it offers a great option for your outdoor vacation.

Explore the best activities and sights in Winnetka

During your outdoor vacation in Winnetka, Illinois, there are plenty of family-friendly activities to enjoy. Explore the nearby forests and nature trails, perfect for hiking and birdwatching. Take a trip to Millennium Park in nearby Chicago to see the iconic Cloud Gate sculpture, or visit the Willis Tower for breathtaking views of the city. In Winnetka itself, you can engage in sports activities like baseball or enjoy a leisurely day of shopping and dining. For more attractions, you can also check out the nearby town of Rosemont or visit Morris Park.

  1. Home Alone House: The Home Alone House is a must-visit attraction for fans of the beloved Christmas movie. This iconic house stands out with its charming architecture and picturesque surroundings. Step into the world of Kevin McCallister as you imagine the hilarious and heartwarming scenes that took place here. The house exudes a cozy and nostalgic atmosphere that will transport you back to the 90s. With its beautifully manicured gardens and quaint neighborhood, the Home Alone House offers a unique experience that will make you feel like a part of the film.
  2. Chocolate Box: The Chocolate Box is a captivating attraction that offers a delightful variety of experiences. From the moment you step inside, you'll be surrounded by a vibrant and energetic atmosphere. Sports enthusiasts can enjoy a game of baseball or indulge in water activities at the nearby lake. Take a leisurely stroll through the stunning gardens and immerse yourself in the beauty of nature. The beach provides a perfect spot for relaxation and sunbathing, while the theater offers entertainment for all ages. Dining options range from casual to upscale, and you can even enjoy live music while savoring delicious cuisine. The Chocolate Box is a sensory delight that will leave you craving for more.
  3. Elder Lane Beach: Elder Lane Beach is a paradise for beach lovers and nature enthusiasts. This family-friendly beach offers a serene and inviting atmosphere. Take a leisurely walk along the shore and enjoy the sound of waves crashing against the shore. The surrounding forests provide a peaceful backdrop, perfect for a picnic or birdwatching. Sports enthusiasts can engage in baseball games or simply relax on the sandy beach. After a day of sun and sand, unwind at one of the nearby dining options and savor a cup of coffee. Elder Lane Beach is a tranquil escape that allows you to reconnect with nature and create lasting memories with your loved ones.

Where to stay in Winnetka

Experience the charm of Winnetka, Illinois on your outdoor vacation. This suburb area offers a range of activities for the whole family. Take a stroll along the scenic lakefront, where you can enjoy the beautiful views and refreshing breeze. Explore the forests and nature trails surrounding Winnetka, perfect for hiking and birdwatching. For sports enthusiasts, catch a baseball game or visit the Northwestern campus nearby. With shopping, family-friendly attractions, and delicious dining options all within walking distance, Winnetka is the ideal destination for a joyful outdoor vacation.

  1. Northfield: Northfield is a charming city that offers a range of family-friendly activities and attractions. You can explore the local shopping scene, with various boutique stores and quaint shops to discover. The city also hosts festivals throughout the year, providing a lively and festive atmosphere for visitors. If you're looking to reconnect with nature, Northfield boasts beautiful forests and parks where you can enjoy outdoor sports, biking, fishing, and canoeing. Additionally, the dining options in Northfield cater to a variety of tastes, ensuring that you and your family will find something delicious to enjoy. With its combination of natural beauty, recreational opportunities, and culinary delights, Northfield is definitely worth a visit for an outdoor vacation with your family.

Best times to go to Winnetka

The travel seasons of Winnetka

Trips to Winnetka show no change in popularity throughout the year. The peak season to visit is from June to August, with July being the highest month. Off-peak season starts from December to February, and October sees the least travelers.

Winnetka has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 73.4 degrees Fahrenheit. The wettest month in Winnetka is May, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January24.8°F (-4.0°C)Light RainMostly Cloudy
February26.2°F (-3.2°C)Light RainMostly Cloudy
March37.0°F (2.8°C)Light RainMostly Cloudy
April46.0°F (7.8°C)Light RainMostly Sunny
May57.0°F (13.9°C)Light RainMostly Sunny
June67.5°F (19.7°C)Light RainMostly Sunny
July73.4°F (23.0°C)Light RainMostly Sunny
August73.0°F (22.8°C)Light RainMostly Sunny
September66.7°F (19.3°C)Light RainMostly Sunny
October54.3°F (12.4°C)Light RainMostly Sunny
November41.5°F (5.3°C)Light RainMostly Sunny
December32.2°F (0.1°C)Light RainMostly Cloudy

Food and dining in Winnetka

While visiting Winnetka, you'll find a variety of delicious local cuisines to satisfy your food cravings. Stacked & Folded Winnetka is a popular restaurant known for its North American dishes, offering a range of flavorful options. For a taste of Latin American cuisine, head to Taco Nano, a highly rated taco restaurant that is sure to impress. If you're in the mood for Mediterranean Greek food, make a stop at Avli Estiatorio, where you can indulge in their highly acclaimed dishes. With options like omelette bars, signature eateries, and the cozy ambiance of Il Lafayette and Indigo Lounge, Winnetka has several restaurants to explore and enjoy.

How do I find a great hotel with Travelocity?

Ensure your entire crew enjoys an unforgettable vacation with our reliable and all-round online travel platform. Discover the perfect accommodations by using our family-friendly badge, which highlights hotels that offer extra amenities for children. Our custom filters make it easy to find hotels that are located near top attractions, provide enhanced cleaning, and fit within your budget.

Why should I book with Travelocity?

Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide worry-free travel every time you and your family book with us so that you can spend less time stressing and more time creating memories. To achieve this, we will assist you in finding and planning your perfect trip, offer transparent pricing and reliable reviews, and provide 24/7 guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Winnetka?

Save money on your trip to Winnetka, Illinois by visiting during the less popular season of December-February. Combine your flights, hotel, and car bookings into a bundle to take advantage of discounted prices. While in Winnetka, enjoy inexpensive activities such as shopping in the local area, exploring the beautiful forests nearby, and taking in a baseball game. These affordable options will allow you to make the most of your family trip without breaking the bank.

Frequently asked questions

What are the top kid-friendly hotels in Winnetka?
Cozy ranch house in wilmette is a great option for families vacationing in Winnetka. With handy amenities like pet-friendly facilities, this kid-friendly hotel will make you and your loved ones feel at home.
Where can I find cheap hotels in Winnetka?
At Travelocity you'll find really nice hotels in Winnetka at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winnetka rather than in Winnetka. We may find you even better rates, too.
How do I find the best Winnetka hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winnetka then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winnetka?
The cheapest hotel in Winnetka is $113. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winnetka?
There are 4,390 hotels in Winnetka on Travelocity.
What are the best hotels in Winnetka?
Winnetka has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winnetka for you!
When is the best time to visit Winnetka?
If you want the joy of a fun-filled trip in peak season, visit Winnetka during March, May and June. If you'd prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
When is the cheapest time to stay in Winnetka?
Based on historic data is usually the cheapest month to visit Winnetka. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winnetka?
There are multiple hotels in Winnetka that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winnetka. We have plenty of kid-friendly hotels in Winnetka to choose from on Travelocity!
Why book a hotel in Winnetka through Travelocity?
Because we have the top hotels in Winnetka! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winnetka on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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