Westchester Packages (Flight + Hotel)

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  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

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

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Top hotels in Westchester

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 ฿5,266 per night from 30 Aug to 31 Aug
฿5,266
฿6,261 total
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (10,191 reviews)
"All the staff was very friendly and the room was clean and well maintained. We enjoyed our stay."

Reviewed on 3 Aug 2026

Congress Plaza Hotel
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 ฿5,360 per night from 17 Aug to 18 Aug
฿5,360
฿6,372 total
17 Aug - 18 Aug
includes taxes & fees
8/10 Very good! (1,904 reviews)
"Great hotel and in a perfect location"

Reviewed on 3 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿7,732 per night from 4 Sept to 5 Sept
฿7,732
฿9,076 total
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very good! (2,365 reviews)
"The rooms were very clean. The front desk was very helpful. Dinner in the restaurant was delicious. Our only complaint was that because we were a party of six with lots of luggage, we needed help. It was hard to find and the guy took all the bags to one of three spaced out rooms and left. We still ..."

Reviewed on 3 Aug 2026

Hilton Chicago O'Hare Airport
See all 4,985 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.

What to do in Westchester

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿904
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

฿1,413
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Art Institute of Chicago

Art Institute of Chicago

฿1,339
per adult
92% of travellers recommend
Art Institute of Chicago
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.