Winnetka Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Winnetka
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
Rp2.708.921
Rp3.220.635 total
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (5,446 reviews)
"It’s OK , well we did book on Expedia. It didn’t show us that we paid a club room which was like a very very very small room for about $600 which is crazy so then we had to go upgrade to a standard. I should think that they should definitely lower the pricing for two nights of that really really ..."
Reviewed on 14 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
Rp3.151.841
Rp3.747.223 total
13 Oct - 14 Oct
includes taxes & fees
8/10 Very good! (2,238 reviews)
"It’s definitely an older style hotel/room. Our first room was very small. Our second room was much nicer and bigger. We also had Chicago police knock on a neighbors door, which of course would make you not at ease. I loved the location. Just probably wouldn’t stay again."
Reviewed on 14 Sept 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
Rp3.068.717
Rp3.648.397 total
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,245 reviews)
"Easy check in, rooms were clean, convenient location."
Reviewed on 14 Sept 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.
Stay near popular Winnetka attractions
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.
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.
What to do in Winnetka
360 CHICAGO Observation Deck
Rp482.247
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Rp651.569
per child
88% of travellers recommend
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?
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
