Book Exclusive Winnetka Vacation Packages

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Winnetka flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $979, price is now CA $603 per person
CA $603
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,428, price is now CA $1,445 per person
CA $1,445
per person
Dec 28 - Jan 2
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,250 per person
CA $1,250
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,337, price is now CA $1,478 per person
CA $1,478
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Art Villa

Art Villa

5 out of 5
West Town
Price was CA $1,551, price is now CA $1,034 per person
CA $1,034
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.

Top Winnetka hotels deals

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 $122 per night
CA $122
CA $143 total
Dec 8 - Dec 9
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Breakfast included
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $149 per night
CA $149
CA $210 total
Nov 25 - Nov 26
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
CA $137 total
Dec 7 - Dec 8
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet 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
Free WiFi
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
CA $193 total
Nov 25 - Nov 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Free WiFi
Restaurant
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
The price is CA $112 per night
CA $112
CA $172 total
Dec 14 - Dec 15
includes taxes & fees
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Free WiFi
Air conditioning
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $114 per night
CA $114
CA $133 total
Nov 25 - Nov 26
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Breakfast included
Pet-friendly
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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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
McCormick Place

McCormick Place

4.5/5(141 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place

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.

Frequently asked questions

How much are vacation packages to Winnetka?
With vacation packages on offer for just CA $603, it's not necessary to max out the credit card for your getaway to Winnetka. Travelocity is here to help. Combine experiences, hotels and flights into a package and land some fantastic discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Winnetka?
No matter your travel style, Travelocity can help you get your hands on an unbeatable Winnetka package deal. The only thing you have to do is pick and choose between our 400 partner airlines and 1,000,000 properties across the globe.
Why should I book my Winnetka vacation bundle with Travelocity?
From amazing destinations to thrilling experiences, we have everything you need to appease your wanderlust. Our 24/7 customer care will also make sure you're taken care of while you're on your getaway. And don't panic if you notice a lower price on your booking, we'll match it. That's our Price Match Guarantee.
Can I save on my Winnetka car rental if I book it with my hotel or flight?
Bundling your flight, car and hotel into a Winnetka vacation package is a great way to land the best prices. Plus, having your own rental car gives you total freedom to make your way to all those big-name sights you're eager to explore. Situated 177 kilometers from Winnetka, University of Wisconsin-Madison is one attraction that should be on your can't-miss list. Put together a driving playlist and make a day trip of it.
Which airport is best for Winnetka?
Many people choose to fly into O'Hare Intl. Airport (ORD), 21 kilometers southwest of downtown Winnetka. Others prefer Midway Intl. Airport (MDW) (32 kilometers away from central Winnetka) or General Mitchell Intl. Airport (MKE) (97 kilometers away from central Winnetka).
What is there to do in Winnetka?
Elder Lane Beach is one of the memorable sights that make Winnetka a popular place to visit. But allow some extra time to explore the city's lesser-known attractions too. This is often where the best vacation memories are made.
Where should I stay when visiting Winnetka?
Many people opt to stay at the North Shore 4 bedroom home near New Trier Schools. It's sure to be a good base for your Winnetka getaway.

Photos of local treasures

Browse Winnetka vacation photos for more inspiration