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Check prices in Winnetka for tonight, May 2 - May 3
May 2 - May 3
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May 3 - May 4
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Check prices in Winnetka for this weekend, May 3 - May 5
May 3 - May 5
Next weekend
Check prices in Winnetka for next weekend, May 10 - May 12
May 10 - May 12

Most frequently booked Winnetka hotels

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
27.48 km from city centre
The price is CA $207 per night
CA $207
per night
May 13 - May 14
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby. Discover genuine guest reviews for Congress Plaza Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Breakfast available
Parking available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
26.13 km from city centre
The price is CA $220 per night
CA $220
per night
May 12 - May 13
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby. Discover genuine guest reviews for River Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Parking available
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
25.43 km from city centre
The price is CA $192 per night
CA $192
per night
May 15 - May 16
Stay at this family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Warwick Allerton - Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
25.39 km from city centre
The price is CA $233 per night
CA $233
per night
May 12 - May 13
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Eurostars Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Spa
Parking available
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
25.23 km from city centre
The price is CA $183 per night
CA $183
per night
May 12 - May 13
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Hotel Felix River North/Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Parking available
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free cancellation
Reserve now, pay when you stay
25.71 km from city centre
The price is CA $159 per night
CA $159
per night
May 9 - May 10
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Aloft Chicago Mag Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Pool
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
26.86 km from city centre
The price is CA $184 per night
CA $184
per night
May 12 - May 13
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Millennium Park are located nearby. Discover genuine guest reviews for Club Quarters Hotel, Central Loop, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Breakfast available
InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Free cancellation
25.82 km from city centre
The price is CA $314 per night
CA $314
per night
May 12 - May 13
Stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for InterContinental Chicago Magnificent Mile, an IHG Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free cancellation
Reserve now, pay when you stay
26.24 km from city centre
The price is CA $205 per night
CA $205
per night
May 12 - May 13
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby. Discover genuine guest reviews for citizenM Chicago Downtown, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Breakfast available
Free WiFi
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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.

Top hotels in Winnetka for Extended Stay

WoodSpring Suites Chicago Addison

WoodSpring Suites Chicago Addison

991 E. Lake Street, Addison, IL
The price is CA $99 per night from May 5 to May 6
CA $99
per night
May 5 - May 6
6/10 (183 reviews)
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.

Cheap Hotels in Winnetka

Pack your bags—it’s time to embark on a getaway. Whether you’re craving a solo retreat or promising your family a vacation to remember, book one of the best hotels in Winnetka. These hotels are located within easy access of the city’s hottest attractions and entertainment, so you won’t miss a beat while you’re in town. Spend the days exploring the local landmarks and the evenings getting to know the nightlife. After exploring the city from top to bottom, rest up at a hotel that speaks to you. Find the perfect place that matches your trip’s vibe, from a trendy boutique to family-friendly accommodations.

Allow us here at Travelocity to pair you with up Winnetka hotels that suit your vacation preferences. Discover places with convenient on-site restaurants, around-the-clock service, and pools where your kids can make a splash. Some hotels may boast fitness rooms and spa services, while others feature game rooms and Wi-Fi access. To top it all off, you’ll score cheap hotels in Winnetka that let you spend more on your activities and less on your lodging. Book and bundle your flight and hotel deals together today and save $$$. It’s time to explore a new city, and break out of your routine.

Winnetka hotels essential information

Accommodation
4,128 hotels
Lowest Price
CA $99
Highest Price
CA $314
Popular hotels
Congress Plaza Hotel, River Hotel, Warwick Allerton - Chicago, Eurostars Magnificent Mile, Hotel Felix River North/Magnificent Mile, Aloft Chicago Mag Mile, Club Quarters Hotel, Central Loop, Chicago, InterContinental Chicago Magnificent Mile, an IHG Hotel, citizenM Chicago Downtown

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 CA $99 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 4,128 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.

Recent Winnetka hotel reviews by fellow wanderers

Freehand Chicago

Freehand Chicago

5 out of 5
Posted 9 hours ago
Travelocity Verified Review
"Good"
A verified traveller stayed at Freehand Chicago
Freehand Chicago

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