Westchester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Westchester Vacation
A great way to experience this lively city is with a tailor-made Westchester vacation package. Stay in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our package deals are all about you. A trip to Westchester is a great opportunity to sightsee. Be sure to visit renowned attractions like Brookfield Zoo, Oakbrook Center Mall and Frank Lloyd Wright Historic District. Don't put off your visit to this city any longer. The perfect Westchester vacation is only a few clicks away with Expedia.
Top Westchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ready to book your vacation to Westchester?
Westchester Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $146
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,961 reviews)
"I was double charged. Still trying to get resolved!!"
Reviewed on Aug 9, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $303
CA $356 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very good! (2,379 reviews)
"Go place to stay if your traveling and have a connection next day. Also very safe! A bit expensive especially the valet parking"
Reviewed on Aug 9, 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
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Chicago By Night River and Lake Cruise
CA $70
per adult
92% of travellers recommend
Frequently asked questions
How much does a Westchester vacation package cost?
You can pick up a vacation package to this destination from CA $1,063 on Expedia. However, how much your vacation to Westchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Westchester?
If you're looking to score a cheap Westchester vacation package, consider travelling in November, December and January. You'll usually find better prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Westchester?
With about 3 days, you'll have enough time to visit popular neighbourhoods such as North Riverside and Fullersburg during your Westchester vacation. Remember to also add Galloping Ghost and Mayslake Peabody Mansion to your must-do list. Up for some more adventures? Consider venturing outside of Westchester on day trips and tours.
How to find the best Westchester package deals?
Use Expedia's filters to find some of the best Westchester package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Westchester package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Westchester vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations separately. Better still, you can personalize your Westchester getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Westchester?
If you've got your Westchester travel dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Westchester?
- Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Westchester.
- Plan your budget wisely: Besides the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, put aside a little extra for unexpected costs that may arise during your trip to Westchester.
- Decide how long to go away for: Now that you're up to speed on Westchester, you can work out the right length of your break. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Westchester vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
