Question 1

How much does a Westchester holiday package cost?

Accepted Answer

You'll find cheap prices from €919 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.

Question 2

What are the cheapest months to go to Westchester?

Accepted Answer

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.

Question 3

How many days is enough for Westchester?

Accepted Answer

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.

Question 4

How to find the best Westchester package deals?

Accepted Answer

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.

Question 5

Is it cheaper to book a Westchester holiday as a package?

Accepted Answer

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.

Question 6

When to book a holiday package to Westchester?

Accepted Answer

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.

Question 7

How to plan a trip to Westchester?

Accepted Answer

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.

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Westchester Holidays

Room 1

Top Flight + Hotel Deals in Westchester

Hotel Felix River North/Magnificent Mile

Swissotel - Chicago

Thompson Chicago, by Hyatt

Hotel Riu Plaza Chicago

LondonHouse Chicago, Curio Collection by Hilton

Top hotels in Westchester

Frequently asked questions

Popular places to visit

Wrigley Field

Navy Pier

Michigan Avenue

What to do in Westchester

Architecture River Tour

Wendella's 90-min Chicago River Architecture Tour

Chicago By Night River & Lake Cruise