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.
Hyatt Place Chicago/ Schaumburg
Save 100% on your flight
Price was $445, price is now $292 per person
$292
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like cooked-to-order breakfast and free self parking.
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 10 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.
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $901, price is now $552 per person
$552
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $712, price is now $443 per person
$443
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the indoor pool and perks like a free area shuttle.
The Blackstone, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $855, price is now $546 per person
$546
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-in are also offered.
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 16 - Nov 17
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
$118 nightly
The price is $139 total per night
$139 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
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
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
4.5/5(1,805 reviews)
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.
Frequently asked questions
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