Deals on vacations and trips to Winnetka

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Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this historic hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Hilton Garden Inn Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a grocery/convenience store are also offered.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

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
$134 nightly
The price is $157 total per night
$157 total
Jul 1 - Jul 2
Total includes 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.
Free WiFi
Restaurant
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $144 total per night
$144 total
Jul 1 - Jul 2
Total includes taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
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
$163 nightly
The price is $192 total per night
$192 total
Jun 30 - Jul 1
Total includes taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
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
$177 nightly
The price is $207 total per night
$207 total
Jun 30 - Jul 1
Total includes taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Spa
Pet friendly
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$166 nightly
The price is $195 total per night
$195 total
Jun 5 - Jun 6
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.
Pet friendly
Free WiFi
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$231 nightly
The price is $271 total per night
$271 total
Jun 29 - Jun 30
Total includes taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Spa
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 cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Frequently asked questions

How much are vacation packages to Winnetka?
With vacation packages on offer for just $402, 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

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