Winnetka Vacations

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Find the Best Winnetka Vacation Packages

Winnetka Hotel Deals

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
Fully refundableReserve now, pay when you stay
The price is AED 584 per night from Apr 21 to Apr 22
AED 584
AED 686 total
includes taxes & fees
21 Apr - 22 Apr
8.2/10 Very Good! (3,906 reviews)
"Very nice, affordable hotel option for families, with large rooms, abundant breakfast, daily room cleaning, nice staff, great location. We liked the included breakfast (only bad thing is that it stops at 9:30), the free daily happy hour with variety of snacks. Location is great, with plenty of dining ..."

Reviewed on 19 April 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 720 per night from May 2 to May 3
AED 720
AED 953 total
includes taxes & fees
2 May - 3 May
8.8/10 Excellent! (2,063 reviews)
"Room cleaning crew paid attention to every detail, even put a small towel under my toiletries."

Reviewed on 18 April 2025

Swissotel - Chicago
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 511 per night from Apr 21 to Apr 22
AED 511
AED 599 total
includes taxes & fees
21 Apr - 22 Apr
8.8/10 Excellent! (2,141 reviews)
"The only thing was the pool was closed. But other then that we had a good stay"

Reviewed on 18 April 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,108 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.

Frequently asked questions

How much does a Winnetka vacation package cost?
Offering excellent value package deals 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?
January, February and November are the best times to search for cheap Winnetka vacation packages. Traveling in quieter periods means you can typically find lower prices on flights and hotels.
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?

  1. Pick your travel dates: What you want to do in Winnetka and your favorite 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 accommodations 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 vacation package that brings all your bookings together.

Discover the most popular places to visit in Winnetka

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 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
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(1,805 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place