Winnetka Holidays

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Top hotels in Winnetka

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
€194
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,455 reviews)
"Perfect location"

Reviewed on 28 Sept 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€168
26 Oct - 27 Oct
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€187
25 Oct - 26 Oct
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 4,399 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.

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 forests or visit its shops.
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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.
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What to do in Winnetka

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

€24
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Winnetka

Frequently asked questions

How much does a Winnetka holiday package cost?
Offering excellent value package deals 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?
  1. Pick your travel dates: What you want to do in Winnetka and your favourite season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

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