Westchester Vacations from ₩686,504
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
The Latest Westchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
₩1,031,707
per person
Nov 16 - Nov 19
found 20 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
8.8/10 Excellent! (2,046 reviews)
Overall good. Still waiting on confirmation that deposit has been refunded to my credit card.
Reviewed on Oct 14, 2026
Find the Best Westchester Vacation Packages
Westchester Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
₩156,010
₩185,480 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very Good! (10,196 reviews)
"Great value and location, comfortable bed with nice bathroom and useful exercise room."
Reviewed on Oct 14, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
₩204,451
₩243,072 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (5,515 reviews)
"Great location with excellent staff!"
Reviewed on Oct 14, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
₩171,752
₩204,196 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very Good! (2,386 reviews)
"Asked for but no wake up call. Some staff … uninterested m. TV problems, air conditoning intermittent and loud"
Reviewed on Oct 14, 2026
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 Westchester vacation package cost?
You'll find cheap prices from ₩686,504 on Expedia for your Westchester getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Westchester costs.
What are the cheapest months to go to Westchester?
If you're hoping to score a cheap Westchester vacation package, consider planning a trip in November, December and January. You'll usually find lower prices on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Westchester?
The ideal duration for your Westchester vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to tick off all the main sights and explore some hidden spots along the way.
How to find the best Westchester package deals?
Bagging a cheap Westchester package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Westchester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Westchester vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Westchester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Westchester?
Land incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Westchester escape.
How to plan a trip to Westchester?
- Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Westchester.
- Set your budget: Factor in expenses like flights, transportation and food when calculating how much to put aside for your trip to Westchester. Then, select a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat.
- Decide how long to go away for: Now that you're more familiar with Westchester, you can work out the right length of your break. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
- Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the ideal Westchester vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
