Book Exclusive Winnetka Vacation Packages

Choose one or more items to build your trip:

Winnetka flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
W Chicago - City Center

W Chicago - City Center

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 1 - Sep. 5
found 7 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Willis Tower and Millennium Park are located nearby.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 1 - Aug. 5
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 4 beach bars, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 1 - Aug. 5
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 1 - Sep. 5
found 7 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 1 - Aug. 5
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Top Winnetka hotels deals

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
The price is CA $166 per night
CA $166
per night
Jul. 1 - Jul. 2
Book a 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.
Breakfast available
Parking available
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
Free cancellation
Reserve now, pay when you stay
The price is CA $218 per night
CA $218
per night
Jul. 7 - Jul. 8
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Pool
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $194 per night
CA $194
per night
Jul. 1 - Jul. 2
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.
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
The price is CA $233 per night
CA $233
per night
Jul. 1 - Jul. 2
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.
Spa
Parking available
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $190 per night
CA $190
per night
Jul. 2 - Jul. 3
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour 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.
Pet-friendly
Spa
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
The price is CA $163 per night
CA $163
per night
Jul. 2 - Jul. 3
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, parking (surcharge), 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.
Pet-friendly
Parking available
Don't see what you're looking for?
See all available properties in Winnetka
View all properties
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.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.

Six Flags Great America
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.

Navy Pier

Winnetka Vacations

A memorable, hassle-free adventure begins with getting to know a bit of information about your destination. It's time to discover the basic details about Winnetka!

Around 16 miles (26 kilometers) northwest of central Chicago, Winnetka is one of the neighborhoods that make this city so charming.

Ready to rub shoulders with the locals? 2,700,000 people live in Chicago.

Places to visit in Winnetka

Everyone knows that being around animals can help reduce stress. So, if always being on the move is tiring you out, why not make your way to Wagner Farm? But that's not all there is. Theater can challenge our world views and asks us to aspire to higher things. Catch a play at Writers Theatre and open your mind to some new ideas.

Where do you fly into for Winnetka?

Flying into O'Hare International Airport (ORD)? Get through security, step out of the terminal and you'll be 12 miles (19 kilometers) southwest from the heart of Winnetka.

Photos of local treasures

Browse Winnetka vacation photos for more inspiration

Frequently asked questions

How much are vacation packages to Winnetka?
Enjoy a fulfilling travel experience in Winnetka with a vacation package starting at CA $878. Locking in your hotels, tours and flights with Travelocity is easy. What’s more, our package deals will leave you with more money in your pocket for plenty of fun times.
Where can I get the best vacation package deals for Winnetka?
Check out Travelocity. With access to 400 air carriers and an incredible 665,000 hotels all over the world, finding the best Winnetka package deal couldn’t be simpler.
Why should I book my Winnetka vacation bundle via Travelocity?
Incredible savings, loads of amazing destinations and 24/7 customer service you can rely on — that’s why. And with our Price Match Guarantee, you can rest assured knowing that you’ll always score the best possible deal with Travelocity.
Can I save money on my Winnetka car rental if I bundle it with my hotel or flight?
Booking a Winnetka vacation package with Travelocity is one of the best ways to save your hard-earned cash. Pick a hotel, car and flight, or any combination of them, and land awesome discounts. You might also want to throw in a few experiences and tours. After you’ve collected the keys to your rental car, venture out of the neighborhood and uncover what the surrounding area has to offer. Approximately 109 kilometersfrom Winnetka, Milwaukee Art Museum justifies a road trip.
What is the best time of year to go to Winnetka?
You’ll nab the best hotel prices in and pay more in . You can usually expect it to be less busy in , while you’ll have plenty more fellow travelers to meet during the months of . It comes down to how much you’re willing to pay, the weather conditions and how you handle crowds.
What is there to do in Winnetka?
Maple Street Beach and Elder Lane Beach have captivated many tourists. Cross these attractions off your must-see list and see what the hype is about.
Where should I stay when visiting Winnetka?
If you’re after somewhere to base yourself in Winnetka, the Historic North Shore Farmhouse Suite is worth considering. Many visitors choose to make a booking at this popular option.
Can I go on vacation to Winnetka at this time?
Learn all the info you should know about travel restrictions and quarantine policies ahead of your flight to Winnetka. Our Covid-19 Travel Advisor is full of advice to help make your trip as hassle-free as possible.