Winnetka Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Winnetka
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
€4,876
per person
8 Oct - 13 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Great staff, very clean property. Enjoyed the café for lattes and cocktails! Breakfast is a fair price for being additional. I loved the location many bars and restaurants just a few minutes walk away.
Reviewed on 19 Aug 2026
Top hotels in Winnetka
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€118
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,267 reviews)
"This is our 2nd time staying here, our 1st was for a wedding held there last year. It was great & we stayed in a renovated room. Amazing & we will be back. Rooms were spacious, very clean, & amazing room. We decided to splurge & upgrade to a lakeside view. Check in was easy, great area, & love that ..."
Reviewed on 20 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€146
9 Sept - 10 Sept
includes taxes & fees
8/10 Very good! (2,047 reviews)
"Great find! We will be back again."
Reviewed on 20 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
€247
12 Sept - 13 Sept
includes taxes & fees
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.
Stay near popular Winnetka attractions
Chocolate Box
Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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
€21
per adult
90% of travellers recommend
Frequently asked questions
How much does a Winnetka holiday package cost?
Offering excellent value package deals from €4,876 on Expedia, you'll be pleasantly surprised at how much a holiday to Winnetka costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winnetka?
January, February and November are the best times to search for cheap Winnetka holiday packages. Travelling in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Winnetka?
Typically, a handful of days is enough to explore the major sights during your Winnetka holiday. But if you prefer to have time to kick back or go on day tours, think about extending your itinerary.
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 holiday as a package?
An Expedia holiday 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 holiday package to Winnetka?
If you're considering a spontaneous Winnetka holiday, 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?
- Pick your travel dates: What you want to do in Winnetka and your favourite season can help you decide when to go.
- Figure out your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your accommodation will likely be the biggest expense during your trip to Winnetka.
- Set the duration of your trip: Start by compiling a list of the attractions and activities you'd like to experience in Winnetka. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Winnetka holiday package that brings all your bookings together.
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- Advocate Illinois Masonic Medical Center
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- Apollo Theater Chicago
- Aragon Ballroom
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- Athenaeum Theatre
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- Camp Pine Woods
- Visit Arcadia Terrace
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- Visit Edison Park
- Visit Jefferson Park
- Visit Rogers Park
- Chippewa Woods
- Chocolate Box
- Visit Des Plaines
- Edge Ice Arena
- Ernest Hemingway Museum and House
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- Kathy Osterman Beach
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- Montrose Harbor
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- Northbrook Village Hall
- Visit Northbrook
- Northwestern University
- Riviera Theatre
- Rosemont Holidays
- Sunset Bridge Meadow
- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
