Westchester Holidays

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Westchester Holiday

Our pick of the best Westchester Hotel Deals

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 NZ$373 per night from 14 Sept to 15 Sept
NZ$373
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,908 reviews)
Nice view
"We got a king room on the top floor overlooking Buckingham Fountain and Lake Michigan. So pretty. Last night we watched the fireworks show off of Navy Pier."

Reviewed on 14 Aug. 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$386 per night from 2 Sept to 3 Sept
NZ$386
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,856 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on 13 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$285 per night from 4 Sept to 5 Sept
NZ$285
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (3,680 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,070 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.

Discover the most popular places to visit in Westchester

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Westchester

River tour boat in Chicago

Architecture River Tour

NZ$69
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$75
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$67
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Westchester

Frequently asked questions

How much does a Westchester holiday 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 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?

  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 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.