Westchester Holidays from AU$837
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
The Latest Westchester Holiday Deals
Swissotel - Chicago
Reviewed on 16 May 2026
The Royal Sonesta Chicago River North
Reviewed on 17 May 2026
Fairmont Chicago at Millennium Park
Reviewed on 18 May 2026
Kimpton Gray Hotel by IHG
Reviewed on 12 May 2026
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
"Always stay here when I’m trying to save money great location and price"
Reviewed on 17 May 2026
Hotel Riu Plaza Chicago
"Friendly attentive staff. Great location- walkable to shopping, restaurants and architectural tours. Nice buffet breakfast. Love the rooftop bar!"
Reviewed on 18 May 2026
The Chicago Hotel Collection - Magnificent Mile
"The front desk staff at night and during the day upon checkout were incredibly warm, welcoming and friendly. Our original hotel was oversold and the front desk staff at that “unnamed” hotel just a few blocks away were awful and rude. It was a welcoming experience to come to this hotel and be greeted ..."
Reviewed on 18 May 2026
Discover the most popular places to visit in Westchester
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
What to do in Westchester
