Winnetka Holidays

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    Better together
    Save up to HK$1,282 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Winnetka

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is HK$1,123 per night from 4 Aug to 5 Aug
HK$1,123
HK$1,319 total
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,910 reviews)
"I loved the history thst comes with this building. The architechture and the inside met all of my expectations. The outside csn be rough for some and if you arent used to or like big city noise this place isnt for you. I love the big city experience and everything thst comes with it!"

Reviewed on 7 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is HK$1,878 per night from 25 Jul to 26 Jul
HK$1,878
HK$2,455 total
25 Jul - 26 Jul
includes taxes & fees
9/10 Wonderful! (1,977 reviews)
"Great hotel."

Reviewed on 5 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is HK$1,383 per night from 10 Jul to 11 Jul
HK$1,383
HK$1,624 total
10 Jul - 11 Jul
includes taxes & fees
8.8/10 Excellent! (2,379 reviews)
"Great location. Nice views of the city. Rooms are great. Beds are small, which is surprising because the rooms are spacious. Parking is frustrating. It’s offsite, not easy to get to, and expensive."

Reviewed on 5 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,384 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

Grant Park

Grant Park

4.5/5(96 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
Soldier Field featuring modern architecture, a city and a high-rise building

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Six Flags Great America showing rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Winnetka

River tour boat in Chicago

Architecture River Tour

HK$383
per adult
94% of travellers recommend
Architecture River Tour
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

HK$235
per adult
84% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

HK$1,115
per adult
92% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
See all activities in Winnetka

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.

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