Westchester Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Westchester Vacation Packages

Westchester Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 635 per night from Aug 3 to Aug 4
SARĀ 635
SARĀ 723 total
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,840 reviews)
"Everything was good"

Reviewed on 17 July 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 714 per night from Aug 10 to Aug 11
SARĀ 714
SARĀ 849 total
10 Aug - 11 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,003 per night from Jul 26 to Jul 27
SARĀ 1,003
SARĀ 1,317 total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,924 reviews)
"Fantastic!"

Reviewed on 17 July 2026

Omni Chicago Hotel
See all 4,892 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.

Frequently asked questions

How much does a Westchester vacation package cost?
You can pick up a vacation package to this destination on Expedia. However, how much your vacation to Westchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Westchester?
If you're looking to score a cheap Westchester vacation package, consider traveling in November, December and January. You'll usually find better prices on airfares and hotels during these quieter months ā€” ideal for a budget-friendly break.
How to find the best Westchester package deals?
Use Expedia's filters to find some of the best Westchester package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Westchester package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Westchester vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations separately. Better still, you can personalize your Westchester getaway to fit 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 vacation package to Westchester?
If you've got your Westchester travel dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Westchester?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to Westchester.
  2. Plan your budget wisely: Besides the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, put aside a little extra for unexpected costs that may arise during your trip to Westchester.
  3. Decide how long to go away for: Now that you're up to speed on Westchester, you can work out the right length of your break. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Westchester vacation package that brings all your bookings together.