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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $720, price is now $513 per person
$513
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,332, price is now $826 per person
$826
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,548, price is now $1,052 per person
$1,052
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,452, price is now $1,046 per person
$1,046
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $897, price is now $652 per person
$652
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.

Top Westchester hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $129 total per night
$129 total
Nov 11 - Nov 12
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.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $181 total per night
$181 total
Nov 1 - Nov 2
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. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $143 total per night
$143 total
Nov 11 - Nov 12
Total with taxes and fees
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, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $169 total per night
$169 total
Nov 9 - Nov 10
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.
Pet friendly
Free WiFi
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $169 total per night
$169 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.
Pool
Pet friendly
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$194 nightly
The price is $230 total per night
$230 total
Nov 13 - Nov 14
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.
Pool
Hot Tub
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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.

Frequently asked questions

How much are vacation packages to Westchester?
Travelocity offers package deals to Westchester, including hotels and flights, starting from an impressive $513. With all the cash you save, you could book some interesting tours or possibly even add on a few extra days to your vacation.
How long should my Westchester vacation be?
The majority of people spend about 3 nights in Westchester, but how long you stay is your call. If you're hoping to discover all the wonderful things this location offers, why not hang around a while longer?
Where can I get the best vacation package deals for Westchester?
Travelocity is here to help you find a Westchester package deal. With no less than 400 air carriers and 1,000,000 properties around the world, you're bound to find the perfect mix.
Why should I purchase my Westchester vacation package with Travelocity?
We have destinations for every type of traveler, exceptional service and 24/7 customer support. And the icing on the cake is we'll match any lower price you're able to find with our Price Match Guarantee.
Can I save money on my Westchester car rental if I book it with my hotel or flight?
Combining your hotel, car and flight into a Westchester vacation package is an excellent way to land the best prices. Plus, having your own set of wheels gives you the freedom to find your way to all the landmarks you can't wait to see. Located 35 mi from Westchester, Six Flags Great America is one attraction that should have a place on your itinerary. Buckle up and make a day trip of it.
Which airport is best for Westchester?
Many people choose to fly into O'Hare Intl. Airport (ORD), 9 mi north of downtown Westchester. Others prefer Midway Intl. Airport (MDW) (8 mi away from central Westchester) or Lewis University Airport (LOT) (20 mi away from central Westchester).
Where should I stay when visiting Westchester?
The Four Points by Sheraton Chicago Westchester/Oak Brook is the first choice of many travelers. Book soon to avoid missing out.

Photos of local treasures

Browse Westchester vacation photos for more inspiration

A calm lake with ducks, autumn trees, and a grassy park area.