Winnetka Vacations from $496
Book a Hotel + Flight or Car together to unlock savings
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.
Level Chicago - River North
Downtown Chicago
$559
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,077 reviews)
Outstanding room. I highly recommend. Be sure to check out the 6th floor and all the amenities!
Reviewed on Sep 23, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$816
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Loved the great upgrade in room and the mini bar selection s
Reviewed on Sep 25, 2026
Stay near popular Winnetka attractions
Maple Street Beach
Why not spend a lazy afternoon at Maple Street Beach during your trip to Winnetka? Amble around the area's forest or visit its shops.
Elder Lane Beach
This lakefront sanctuary offers a serene escape with pristine sandy shores and Lake Michigan views. Enjoy a peaceful afternoon in the adjacent park with its well-maintained picnic areas and playground.
What to do in Winnetka
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Winnetka Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
$186 nightly
$221 total
Oct 25 - Oct 26
Total with taxes and fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$153 nightly
$181 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (10,224 reviews)
"Terrible male and female bar staff! Don’t interact with customers, arguing about cups, don’t ask customer if they want a drink or to order food! They are two miserable old men"
Reviewed on Sep 25, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$179 nightly
$213 total
Oct 25 - Oct 26
Total with taxes and fees
8/10 Very Good! (2,346 reviews)
"It was modern, but my room wasn't great. The door that covered the fridge was broken. There wasn't even water in the room. The location was the best part."
Reviewed on Sep 26, 2026
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 $496 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.