Deals on vacations and trips to Westchester
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Westchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was $380, price is now $243 per person
$243
per person
Jan 16 - Jan 18
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Art Villa
West Town
Save 100% on your flight
Price was $1,307, price is now $711 per person
$711
per person
Feb 5 - Feb 9
found 22 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,169, price is now $694 per person
$694
per person
Feb 5 - Feb 9
found 22 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $413, price is now $251 per person
$251
per person
Jan 16 - Jan 18
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $400 per person
$400
per person
Jan 16 - Jan 18
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Top Westchester hotels deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $112 total per night
$112 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $115 total per night
$115 total
Dec 7 - Dec 8
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
citizenM Chicago Downtown
80 East Wacker Place Chicago IL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $134 total per night
$134 total
Nov 19 - Nov 20
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $104 total per night
$104 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. WiFi in public areas is free.
Free WiFi
Air conditioning
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $150 total per night
$150 total
Dec 8 - Dec 9
Total with taxes and fees
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Breakfast included
Free WiFi
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $108 total per night
$108 total
Dec 7 - Dec 8
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Breakfast included
Pet friendly
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.
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
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