Winnetka Holidays from AU$1,839

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Your Winnetka Holiday

When a city stay is calling, answer it with a holiday package to Winnetka. With all your travel needs in place before you leave, all you have to do here is focus on having the time of your life. Northwestern University, Chicago Botanic Garden and The Glen Club are just some of the many sights worth exploring during your trip to Winnetka. Expedia can help you escape your daily routine. Tailor your holiday to Winnetka to suit your style of travel, whatever that may be!

The Latest Winnetka Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was AU$3,931, price is now AU$1,839 per person
AU$1,839
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,617 reviews)
Would definitely book a stay again.

Reviewed on 16 Aug. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$4,291, price is now AU$1,977 per person
AU$1,977
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Great area: able to walk to many restaurants.

Reviewed on 18 Aug. 2025

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
Price was AU$4,182, price is now AU$1,929 per person
AU$1,929
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
The room was great The staff was very friendly free coffee in the morning was nice

Reviewed on 14 Aug. 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,232, price is now AU$1,966 per person
AU$1,966
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean

Reviewed on 18 Aug. 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$3,992, price is now AU$1,855 per person
AU$1,855
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.

Reviewed on 17 Aug. 2025

Winnetka Holiday

Winnetka Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
12,500
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Rosemont Theatre, Riviera Theatre and Parkway Bank Park Entertainment District

Our pick of the best Winnetka Hotel Deals

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 AU$243 per night from 1 Sept to 2 Sept
AU$243
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,944 reviews)
"It takes around 20min for the hot shower to come out."

Reviewed on 17 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 AU$272 per night from 3 Sept to 4 Sept
AU$272
3 Sept - 4 Sept
includes taxes & fees
8.2/10 Very Good! (1,187 reviews)
"Everything was great. Thanks for an awesome experience."

Reviewed on 15 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 AU$290 per night from 3 Sept to 4 Sept
AU$290
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,723 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"

Reviewed on 17 Aug. 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,447 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.
All Inclusive Holidays
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Discover the most popular places to visit in Winnetka

Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Winnetka

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Winnetka

Frequently asked questions

How much does a Winnetka holiday package cost?
Offering excellent value package deals from AU$1,839 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.

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