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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Apr. 17 - Apr. 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Millennium Park 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
Apr. 4 - Apr. 11
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) 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 helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Apr. 17 - Apr. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 3-star B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Mar. 15 - Mar. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Mar. 14 - Mar. 19
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) 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 Millennium Park 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 $133 per night
CA $133
CA $156 total
includes taxes & fees
25 Jan - 26 Jan
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 Millennium Park and Michigan Avenue are located nearby.
Free WiFi
Restaurant
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 $126 per night
CA $126
CA $148 total
includes taxes & fees
2 Feb - 3 Feb
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 Michigan Avenue and Millennium Park are located nearby.
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 $134 per night
CA $134
CA $157 total
includes taxes & fees
20 Feb - 21 Feb
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 Millennium Park are located nearby.
Spa
Free WiFi
Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $236 per night
CA $236
CA $336 total
includes taxes & fees
4 Feb - 5 Feb
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
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 $142 per night
CA $142
CA $167 total
includes taxes & fees
5 Feb - 6 Feb
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel

Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is CA $175 per night
CA $175
CA $206 total
includes taxes & fees
30 Jan - 31 Jan
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
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

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
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 entertainment choices in this vibrant area.

Wrigley Field
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 theater 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 $776, 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