Deals on vacations and trips to Winnetka

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Winnetka flight + hotel vacation 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
Save 100% on your flight
Price was $797, price is now $495 per person
$495
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,797, price is now $1,020 per person
$1,020
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,176, price is now $1,273 per person
$1,273
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,739, price is now $1,039 per person
$1,039
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,623, price is now $1,033 per person
$1,033
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, dry cleaning, and luggage storage are also on offer.

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
$107 nightly
The price is $125 total per night
$125 total
Apr 5 - Apr 6
Total with taxes and fees
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 and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
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
$119 nightly
The price is $140 total per night
$140 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.
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
$127 nightly
The price is $149 total per night
$149 total
Apr 12 - Apr 13
Total with taxes and fees
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 a grocery/convenience store are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$146 nightly
The price is $172 total per night
$172 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
$221 nightly
The price is $260 total per night
$260 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $169 total per night
$169 total
Apr 27 - Apr 28
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.
Pool
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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

Wrigley Field

4.5/5(2,149 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
McCormick Place

McCormick Place

4.5/5(1,830 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

Frequently asked questions

How much are vacation packages to Winnetka?
With vacation packages on offer for just $495, 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 110 mi 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), 13 mi southwest of downtown Winnetka. Others prefer Midway Intl. Airport (MDW) (20 mi away from central Winnetka) or General Mitchell Intl. Airport (MKE) (60 mi 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

Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.