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 Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $524, price is now $277 per person
$277
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $817, price is now $448 per person
$448
per person
Oct 31 - Nov 2
found 2 days 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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,342, price is now $767 per person
$767
per person
Dec 2 - Dec 8
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. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,089, price is now $632 per person
$632
per person
Dec 11 - Dec 14
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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,018, price is now $619 per person
$619
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Top Westchester hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $179 total per night
$179 total
Oct 26 - Oct 27
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $163 total per night
$163 total
Oct 27 - Oct 28
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$201 nightly
The price is $236 total per night
$236 total
Oct 29 - Oct 30
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.
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $189 total per night
$189 total
Oct 20 - Oct 21
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
$203 nightly
The price is $238 total per night
$238 total
Oct 30 - Oct 31
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.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $234 total per night
$234 total
Oct 1 - Oct 2
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.
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.
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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