Search Deals onWestchester Vacation Packages
Westchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
Save 100% on your flight
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.
Swissotel - Chicago
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Staybridge Suites Chicago - Glenview by IHG
Save 100% on your flight
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 3-star golf hotel in Glenview. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kohl Children's Museum and Glenview Prairie Golf Club are located nearby.
Hilton Chicago O'Hare Airport
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Courtyard by Marriott Chicago Magnificent Mile
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Fairmont Chicago at Millennium Park
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Westchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Westchester Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Apr 10 - Tue, Apr 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Sat, Apr 19 - Wed, Apr 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Fri, Jun 20 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,013 Roundtrip, found 4 days ago
$1,013
Roundtrip
found 4 days ago
Sat, Apr 19 - Sat, May 3
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,059 Roundtrip, found 5 days ago
$1,059
Roundtrip
found 5 days ago
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