Winnetka Holidays from AU$3,142

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
23 Oct - 30 Oct
found 4 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location was good. Staff was friendly. It was clean. But it was hard to enjoy time in the room because of the TV. They had horrible cable with nothing on, and it wasn’t a smart tv so we couldn’t log into any of our streaming services or even stream from our phones to the tv. We had to go out and buy a firestick.

Reviewed on 10 Aug. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
23 Oct - 30 Oct
found 4 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on 11 Aug. 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
23 Oct - 30 Oct
found 4 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul. 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
per person
23 Oct - 30 Oct
found 4 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
Ran into some confusion with my credit card. It was used at check in and then they said they didn’t have it

Reviewed on 9 Aug. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
23 Oct - 30 Oct
found 4 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Beautiful hotel in great location. The food option at hotel are great with good food. It is walkable to surrounding attractions.

Reviewed on 10 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$453 per night from 7 Sept to 8 Sept
AU$453
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,945 reviews)
"I love the location."

Reviewed on 11 Aug. 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$350 per night from 4 Sept to 5 Sept
AU$350
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,848 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on 11 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$283 per night from 26 Aug to 27 Aug
AU$283
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (3,660 reviews)
"Great rooms, comfortable, walking distance to anywhere you’d want to go."

Reviewed on 10 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,577 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
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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$64
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$3,142 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.