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.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was $391, price is now $235 per person
$235
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $956, price is now $555 per person
$555
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $533, price is now $313 per person
$313
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $612, price is now $362 per person
$362
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $549, price is now $329 per person
$329
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Top Westchester hotels deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $105 total per night
$105 total
Jan 5 - Jan 6, 2026
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.
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $179 total per night
$179 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $149 total per night
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A library, express check-in, and express check-out are also on offer.
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $103 total per night
$103 total
Jan 24 - Jan 25, 2026
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and express check-out are also on offer.
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $173 total per night
$173 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Eurostars Magnificent Mile
660 North State Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $110 total per night
$110 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
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
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.
Frequently asked questions
Photos of local treasures
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