Deals on vacations and trips to Westchester

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Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $783, price is now $549 per person
$549
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,010, price is now $627 per person
$627
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,158, price is now $836 per person
$836
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,128, price is now $819 per person
$819
per person
Dec 24 - Dec 29
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.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $843, price is now $619 per person
$619
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.

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
$107 nightly
The price is $127 total per night
$127 total
Nov 23 - Nov 24
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
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
$116 nightly
The price is $138 total per night
$138 total
Dec 1 - Dec 2
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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $117 total per night
$117 total
Dec 10 - Dec 11
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 Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $141 total per night
$141 total
Nov 23 - Nov 24
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
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
$116 nightly
The price is $138 total per night
$138 total
Nov 23 - Nov 24
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
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $190 total per night
$190 total
Nov 22 - Nov 23
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 $549. 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.