Westchester Vacations from $363
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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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,259, price is now $716 per person
$716
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.
Reviewed on Dec 31, 2025
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,257, price is now $755 per person
$755
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Views were great balcony included but bed was uncomfortable
Reviewed on Dec 30, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $610, price is now $368 per person
$368
per person
Mar 4 - Mar 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Had a great dinner at Fora before a very short walk to the new years eve event we were headed to and then came back for a great night's sleep in a very comfortable room! All the staff we interacted with were great!
Reviewed on Jan 1, 2026
La Banque Hotel
Price was $803, price is now $484 per person
$484
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.
Reviewed on Nov 30, 2025
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See all available trips from Columbus to Westchester
View all tripsDiscover the most popular places to visit in Westchester
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Westchester
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Westchester Hotel Deals
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 11 to Jan 12
$192 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (2,445 reviews)
Best option for us while attending an event at McCormick place, with ability to park in public parking that is cheaper than the hotel parking!
Reviewed on Dec 30, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 8 to Jan 9
$105 total
Jan 8 - Jan 9
Total with taxes and fees
8.8/10 Excellent! (3,613 reviews)
Clean room , great location.
Reviewed on Dec 30, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Jan 11 to Jan 12
$192 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (2,201 reviews)
Easy Peasy. Beautiful hotel at a great price.
Reviewed on Jan 1, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
