Westchester Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
Top Flight + Hotel Deals in Westchester
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
€1,400
per person
27 Nov - 3 Dec
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9/10 Wonderful! (1,489 reviews)
Nice room and great location…need a restaurant and real bar-bar is sort of open…would like to see it after they really rebrand everything
Reviewed on 4 Oct 2026
Stay One Chicago
Downtown Chicago
€2,032
per person
27 Nov - 3 Dec
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8/10 Very good! (14 reviews)
The instructions on how to access the room were excellent and the room was well maintained and well stocked. Excellent choice for the price and location.
Reviewed on 2 Oct 2026
Cambridge Inn on Main
€2,708
per person
17 Dec - 21 Dec
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (74 reviews)
Everything about this hotel was great! A very historic Boutique Hotel that takes you back in time! Each room has a theme of its own which is unique to the period. The owner was very friendly and made sure that I had everything that I needed to make my stay excellent! If you're ever in that area or even doing business in the Madison Wisconsin area you may consider taking an extra half hour to drive to this hotel and stay there. I don't think you'll be disappointed at all as a matter of fact I would be surprised if you didn't like it. I've been in hotels halfway around the world and I must say that next time I'm back in that area I will be staying here!
Reviewed on 4 Oct 2026
Top hotels in Westchester
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€135
1 Nov - 2 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
€176
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€123
9 Oct - 10 Oct
includes taxes & fees
8/10 Very good! (2,417 reviews)
"The staff was just blatantly unhelpful. The front desk was often unmanned and could not take requests whether it was for a checkout or to ask about how a food delivery had been misplaced. I’ve seen HolidayInns with better customer service."
Reviewed on 5 Oct 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.
What to do in Westchester
Frequently asked questions
How much does a Westchester holiday package cost?
You'll find cheap prices from €1,400 on Expedia for your Westchester getaway. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Westchester costs.
What are the cheapest months to go to Westchester?
If you're hoping to score a cheap Westchester holiday 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 holiday 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 personalise 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Westchester holiday as a package?
Expedia holiday 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 personalised Westchester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 accommodation and airfare: After you've nailed down your trip dates and duration, book the ideal Westchester holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
