Westchester Packages (Flight + Hotel)

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    Save up to ฿4,531 when you book a flight and hotel together*
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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 ฿6,108 per night from 14 Sept to 15 Sept
฿6,108
฿7,171 total
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,984 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"

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 ฿5,631 per night from 2 Sept to 3 Sept
฿5,631
฿7,422 total
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,849 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on 11 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 ฿4,665 per night from 4 Sept to 5 Sept
฿4,665
฿5,476 total
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,077 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

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

Millennium Park

What to do in Westchester

River tour boat in Chicago

Architecture River Tour

฿1,358
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

฿1,474
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

฿1,327
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.