Winnetka Holidays

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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 S$166 per night from 1 Jan to 2 Jan
S$166
includes taxes & fees
1 Jan - 2 Jan,2025
7.8/10 Good! (8,271 reviews)
"I will never stay at another hotel in this area. The Congress is not only affordable (even the lake view options) but it is beautiful! The high ceilings and natural light in the rooms is unbeatable! My experience is always seamless and the staff are so helpful!"

Reviewed on 24 Dec,2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$166 per night from 16 Jan to 17 Jan
S$166
includes taxes & fees
16 Jan - 17 Jan,2025
8.6/10 Excellent! (3,620 reviews)
"Amazing location, lots of shopping and great food within a walkable distance (0.3-1mi). Only downside was the bathroom products, the soap they provide makes your skin incredibly dry which is terrible in combination with the cold weather."

Reviewed on 24 Dec,2024

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$276 per night from 19 Jan to 20 Jan
S$276
includes taxes & fees
19 Jan - 20 Jan,2025
9/10 Wonderful! (3,106 reviews)
"Very friend and helpful staff. The onsite restaurants were great. Close to everything."

Reviewed on 24 Dec,2024

Hyatt Regency Chicago
See all 4,123 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 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 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

What to do in Winnetka

Flyover in Chicago

Flyover in Chicago

S$52
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$66
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

S$46
per adult
Color Factory Chicago Ticket
See all activities in Winnetka

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.