Winnetka Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winnetka

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is 4.949.475 ₫ per night from 14 Sept to 15 Sept
4.949.475 ₫
5.810.190 ₫ total
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is 3.973.263 ₫ per night from 1 Sept to 2 Sept
3.973.263 ₫
4.664.213 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"

Reviewed on 19 Aug 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is 4.012.652 ₫ per night from 4 Sept to 5 Sept
4.012.652 ₫
4.710.452 ₫ total
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (4,726 reviews)
"Valet parking was very expensive for leaving your car without using it for 2 days."

Reviewed on 20 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,480 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

McCormick Place
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

Millennium Park

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.