Westchester Vacations from $597
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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.
The Latest Westchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,555, price is now $945 per person
$945
per person
Sep 24 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $945, price is now $631 per person
$631
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Awful experience will not be going back ever again
Reviewed on Jul 16, 2026
Don't see what you're looking for?
See all available trips from Columbus to Westchester
View all tripsWhat to do in Westchester
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Westchester Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from Aug 3 to Aug 4
$193 total
Aug 3 - Aug 4
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $226 total per night from Jul 19 to Jul 20
$226 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,759 reviews)
"The worse experience I’ve ever had"
Reviewed on Jul 16, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $351 total per night from Jul 26 to Jul 27
$351 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,920 reviews)
"Employees very professional and restaurant/bar clean 👌 food & drinks fresh and hot 👏 The location of the hotel is Walking distance ,from shop,food restaurants and Tourist attractions,great place to stay 😀 and the Obama Presidential Center only 9 mile from hotel omni, Me and Wife enjoyed ourselves ..."
Reviewed on Jul 16, 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 |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Holy Name Cathedral
- Marina City
- Richard J. Daley Center
- Lincoln Park Conservatory
- Our Lady of Sorrows Basilica
- Advocate Illinois Masonic Medical Center
- Picasso Statue
- Monique Meloche Gallery
- Film Row Cinema
- Chicago Vacations
- Chicago Museum Campus Vacations
- Depaul University-Loop Campus
- Brookfield Vacations
- Bally's Casino Chicago
- Roosevelt University
- Cantigny Park
- Garfield Park Conservatory
- Michigan Avenue Bridge
- West Loop Vacations
- Anna and Frederick Douglass Park
- North Avenue Beach
- Skydeck Ledge
- Shops at North Bridge
- Civic Opera House
- Ping Tom Memorial Park
- Garfield Park
- Maxwell Street Market
- Rookery
- Goodman Theater
- Grace Abbott Homes Vacations
- Armitage Avenue
- Lincoln Park Zoo
- Canalport Riverwalk Park
- Chase Tower
- International Museum of Surgical Science
- Jane Addams' Hull-House Museum
- St. John Cantius Church
- Wrigley Building
- Oak Brook Golf Course
- American Police Center & Museum
- Holy Trinity Russian Orthodox Cathedral
- 333 West Wacker Drive
- Driehaus Museum
- St Nicholas Ukrainian Catholic Cathedral
- Auditorium Building and Theatre
- Humboldt Park
- Raging Waves Waterpark
- Montrose Beach
- 311 S Wacker Dr
- Marshall Field Building
- Robie House
- Mary Bartelme Park
- Centennial Beach
- Cadillac Palace Theatre
- Michigan Avenue
- Chicago Place Mall
- Illinois Centennial Memorial Column
- Carbide and Carbon Building
- Magnificent Mile Vacations
- Mayslake Peabody Mansion
- Chicago City Hall
- Bridgeport Art Center
- Fisher Building
- Cooking & Hospitality Institute of Chicago
- Graue Mill and Museum
- Merchandise Mart
- Art Institute of Chicago
- York Woods County Forest Preserve
- The Salt Shed
- Legoland® Discovery Center
- Bellwood Vacations
- St. Josaphat Church
- Flat Iron Building
- Depaul University-Lincoln Park
- Fourth Presbyterian Church
- House of Blues Chicago
- Wicker Park Vacations
- University of Illinois Chicago
- Navy Pier
- Hines Vacations
- Ohio Street Beach
- Wrigley Field
- Cibc Theatre
- The East Bank Club
- Zhou B Art Center
- Chicago Cultural Center
- Willis Tower
- Gorilla Tango Theatre
- 900 North Michigan Shops
- Galloping Ghost
- St. Basil Greek Orthodox Church
- Morton Arboretum
- Chinatown Vacations
- Tribune Tower
- Packer Schopf Gallery
- Chicago Children's Museum
- Unity Temple
- Goose Island Vacations
- Broadview Vacations
- Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
