Westchester Vacations from $638
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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.
The Latest Westchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
$638
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
This hotel is well-maintained with clean, quiet, well-appointed, spacious rooms. Some have very nice views of Chicago and/or the River and Lake Michigan. The staff members were friendly and helpful, although I think I'm going to have to call them to get an itemized bill for my incidental room charges (usually such bills are emailed). This might be because I booked through Expedia. The location is great for exploring the loop as well as River North. I will definitely consider staying there again.
Reviewed on Aug 31, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$1,124
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Loved it and definitely feel like the bathroom was made for the girls! Just wish we had gotten a response for requests we madr but other than that it was a good hotel! Loved the breakfast.
Reviewed on Aug 31, 2026
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Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Westchester Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$113 nightly
$135 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (10,237 reviews)
"Room was clean, bathroom was old and a bit smelly. Was fine for the one night we were there - a bit pricey tho"
Reviewed on Aug 31, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
$181 total
Sep 27 - Sep 28
Total with taxes and fees
8/10 Very Good! (2,133 reviews)
"Loved this hotel, great location and wonderful accommodations, just perfect"
Reviewed on Aug 31, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (882 reviews)
"Love the layout. Great location. Super easy check in and check out"
Reviewed on Aug 30, 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.
Find the Best Westchester Vacation Packages
Westchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 16,700 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District |
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Frequently asked questions
How much does a Westchester vacation package cost?
You'll find cheap prices from $638 on Expedia for your Westchester getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Westchester costs.
What are the cheapest months to go to Westchester?
November, December and January are the best times to search for cheap Westchester vacation packages. Opting to travel in quieter periods means you can typically find better prices on accommodations and flights.
How many days is enough for Westchester?
Generally, a handful of days is enough to tick off the top attractions during your Westchester vacation. However, if you want to have more time to relax or take day tours, consider extending your trip.
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 personalize 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 traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Westchester vacation as a package?
Expedia vacation 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 personalized Westchester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Westchester vacation packages?
Secure your ideal getaway to Westchester with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up bargains before they disappear.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
