Winnetka Vacations from $354

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Your Winnetka Vacation

When a city adventure is calling, answer it with a Winnetka vacation package. With all your travel needs in place before you leave, all you have to do here is focus on making unforgettable memories. Fill your free time with tours of Chicago Botanic Garden, The Glen Club and North Shore Center for the Performing Arts, some of the attractions you simply have to see during your trip to Winnetka. Browse Expedia's wide range of travel options and begin planning your perfect vacation to Winnetka now.

The Latest Winnetka vacation packages

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $628, price is now $354 per person
$354
per person
Apr 3 - Apr 6
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.

Reviewed on Nov 30, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,004, price is now $541 per person
$541
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast was great, room was super nice and upgraded

Reviewed on Jan 8, 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,015, price is now $561 per person
$561
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room

Reviewed on Jan 5, 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $742, price is now $448 per person
$448
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Th staff was mostly helpful, Jennifer that was in charge of the pool fitness area was very helpful, she gave us information on family restaurants cheap close to the hotel to eat at the first night we were in town, she was a gem, the hotel itself needs a lot of work, the windows in the room we stayed in were very drafty and we had issues keeping the room warm, the surprise costs was a shock to us, they don’t disclose the fact that they charge the paying guests at the hotel to park in the garage, the fact that they charge guests to use the pool and the fitness areas is just crazy, the pool area and hot tubs were not anything special and most hotels do not charge guests to use the amenities, we won’t be staying with the Hilton anywhere in the USA again even if we are given free room, we just weren’t impressed, it was just a basic hotel to us,

Reviewed on Jan 6, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,021, price is now $621 per person
$621
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

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Discover the most popular places to visit in Winnetka

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

Michigan Avenue

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 cbd, a sporting event and a city

Wrigley Field

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

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

Navy Pier

What to do in Winnetka

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$83
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Winnetka

Winnetka Hotel Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 18 to Jan 19
$105 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (3,660 reviews)
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.

Reviewed on Jan 6, 2026

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 15 to Jan 16
$192 total
Jan 15 - Jan 16
Total with taxes and fees
8.4/10 Very Good! (2,506 reviews)
The hotel property was amazing! Numerous options for dining and relaxing. The room was clean and inviting.

Reviewed on Jan 8, 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $193 total per night from Jan 15 to Jan 16
$193 total
Jan 15 - Jan 16
Total with taxes and fees
8.4/10 Very Good! (2,226 reviews)
Room was very clean and staff was great

Reviewed on Jan 6, 2026

Palmer House a Hilton Hotel
See all 4,651 properties in Winnetka
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.

Find the Best Winnetka Vacation Packages

Winnetka Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
12,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Montrose Beach

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Frequently asked questions

How much does a Winnetka vacation package cost?
Offering excellent value package deals from $354 on Expedia, you'll be pleasantly surprised at how much a vacation to Winnetka costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winnetka?
You can typically find reduced prices and better availability in December, January and February. Check out our cheap Winnetka vacation packages and you could land some great off-season deals.
How many days is enough for Winnetka?
The ideal duration for your Winnetka vacation depends on what you'd like to do. Typically, a few days to a week will give you enough time to hit all the main attractions and explore some hidden gems along the way.
How to find the best Winnetka package deals?
Begin your search for a Winnetka package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winnetka package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winnetka getaway off to a flying start.
Is it cheaper to book a Winnetka vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels individually. Better still, you can tailor your Winnetka getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winnetka?
If you're considering a spontaneous Winnetka vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Winnetka?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favorite season and the type of activities on offer will also help you decide when to vacation in Winnetka.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will probably be the biggest expense during your trip to Winnetka.
  3. Organize your Winnetka getaway with Expedia's trip planning tool: Look for and book stays and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Winnetka together.
  4. Determine how many days away: Start by making a list of all the activities and sights you'd like to get to in Winnetka. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Winnetka vacation package.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some incredible things to do in Winnetka in Winnetka. Book tickets or make reservations before you go to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Winnetka vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Winnetka break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.