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.
La Banque Hotel
Save 100% on your flight
per person
Jun 22 - Jun 25
found 5 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Staybridge Suites Chicago O'Hare - Rosemont by IHG
O'Hare
Save 100% on your flight
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
Save 100% on your flight
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a grocery/convenience store are also offered.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
O'Hare
Save 100% on your flight
per person
Aug 1 - Aug 8
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Top Westchester hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $157 total per night
$157 total
May 26 - May 27
Total includes 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.
Free WiFi
Restaurant
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$165 nightly
The price is $193 total per night
$193 total
May 27 - May 28
Total includes 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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $199 total per night
$199 total
May 27 - May 28
Total includes 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
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $136 total per night
$136 total
May 27 - May 28
Total includes taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking.
Air conditioning
Gym
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $214 total per night
$214 total
May 26 - May 27
Total includes 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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Spa
Pet friendly
River Hotel
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $164 total per night
$164 total
May 27 - May 28
Total includes 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. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
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.
Six Flags Great America
4.5/5(347 reviews)
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
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.
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