Westchester Holidays

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Your Westchester Holiday

Book a tailored Westchester holiday package that includes everything you need and nothing you don't. Good for nightlife, bars and pubs and cafes, consider staying in the neighbourhood of Wicker Park. Any trip to Westchester needs a well-planned itinerary. Fill yours with leading attractions like Brookfield Zoo, Oakbrook Centre Mall and Ernest Hemingway Museum and House. Your dream Westchester holiday is only clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.

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Westchester Holiday

Westchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
16,700
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Rosemont Theatre, Brookfield Zoo and Parkway Bank Park Entertainment District

Our pick of the best Westchester 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$154 per night from 24 Nov to 25 Nov
AU$154
includes taxes & fees
24 Nov - 25 Nov
7.8/10 Good! (8,119 reviews)
"It is an old building so We were very pleased with how clean the rooms were. Tub drained slowly but did not affect our shower schedules. Radiator was a little confusing but it didn’t bother is because the weather was beautiful. Will stay again"

Reviewed on 20 Nov. 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 AU$180 per night from 23 Dec to 24 Dec
AU$180
includes taxes & fees
23 Dec - 24 Dec
8.6/10 Excellent! (3,544 reviews)
Book with confidence!
"Booked: two bedroom suite Condition: bed was very comfy and linens felt lovely. Bathroom was well appointed. Spotlessly clean. Rooms could use a remodel and a spruce up, BUT it was not offensively outdated and I have NO complaints on the quality of the space. Microwave also functions as a convection ..."

Reviewed on 20 Nov. 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 22 Dec to 23 Dec
AU$173
includes taxes & fees
22 Dec - 23 Dec
8.4/10 Very Good! (3,262 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

Reviewed on 21 Nov. 2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,584 properties in Westchester
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

Frequently asked questions

How much does a Westchester holiday package cost?
From just . Yes, you read that correctly. Our Westchester packages are a simple way to make your budget stretch further. Combine your flights, hotels and rental car and get to know this exciting destination.
How do I get a cheap travel package to Westchester?
Combine your flight and hotel bookings, throw in extras such as a rental car or activities, and save with a Westchester holiday package. You won’t just walk away with superb discounts on your escape — you’ll have loads of choice within your reach too. When you book through Expedia, you can choose from more than 550 air carriers and 1 000 000 hotels around the globe. Your affordable holiday begins right here, right now!
Where should I stay in Westchester?
A getaway to Westchester wouldn’t be complete without paying a visit to Brookfield Zoo, Oak Brook Golf Course and Galloping Ghost. Spend your evenings close to these top sights and make sightseeing simple.
What are the top hotels in Westchester?
When it comes to comfortable places to stay in Westchester, you can’t beat Four Points by Sheraton Chicago Westchester/Oak Brook. Browse our deals and pick up a bargain.
How far in advance should I book my Westchester holiday?
The earlier, the better. Airlines generally release flight tickets up to 12 months ahead of departure, and this is a great opportunity to land some of the lowest prices. Just been told you should take all your holiday days in a few weeks? No problem! Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Westchester travel package include?
Hotels, rental cars and flights — we have them covered. With Expedia, you can create your Westchester travel package just how you like it. All you have to do is decide just what you need. Once you’ve made your booking, you can add on fun things like activities and tours. The more you bundle, the more you save!
What should I know before booking a Westchester travel package?
When you book your hotels, flights and car rentals together, you’ll land amazing discounts. Whether you’re organising a mountain getaway in a cabin or want to stay in a luxurious city hotel, Expedia will make it happen for less.
Can I choose my airline with a Westchester Expedia holiday package?
With a holiday package, you’re in charge. Whether you’d prefer to fly to Westchester in coach or first class, simply select from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Westchester holiday package?
It’s hard to predict what tomorrow might bring, so it’s comforting to know that you can change or cancel your Westchester holiday package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for more information.

Discover the most popular places to visit in Westchester

McCormick Place

McCormick Place

4.5/5(21 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
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
United Center

United Center

5/5(8 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

United Center

What to do in Westchester

Flyover in Chicago

Flyover in Chicago

AU$58
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

AU$68
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

AU$82
Per adult
94% of travellers recommend
Architecture River Tour
See all activities in Westchester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.