Westchester Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Westchester Vacation Packages

Westchester Hotel Deals

InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ₩218,452 per night from Jul 2 to Jul 3
₩218,452
₩299,994 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,948 reviews)
"Nice place, service unremarkable. My one pet peeve - the bathroom light automatically turns on when you enter. In the middle of the night, quite jarring. A night light would be preferred"

Reviewed on Jun 30, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩195,518 per night from Jul 7 to Jul 8
₩195,518
₩229,517 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (2,355 reviews)
"Hard to located without sign took us 30 minutes to find hotel"

Reviewed on Jun 29, 2025

Hilton Chicago/Magnificent Mile Suites
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 ₩194,769 per night from Jul 3 to Jul 4
₩194,769
₩228,640 total
Jul 3 - Jul 4
includes taxes & fees
7.8/10 Good! (8,892 reviews)
"It was in a great location. My friends and I had a great stay here and were super close to Millenium park. Bus stops were close and the hotel was great overall. Parking was expensive so make sure to book it somewhere else beforehand as well. You will find better deals that way."

Reviewed on Jun 29, 2025

Congress Plaza Hotel
See all 4,925 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'll find cheap prices 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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the ideal Westchester vacation package for you.

Discover the most popular places to visit in Westchester

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.