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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $855, price is now $599 per person
$599
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,349, price is now $2,117 per person
$2,117
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,396, price is now $901 per person
$901
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,352, price is now $889 per person
$889
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,068, price is now $703 per person
$703
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
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 lobby fireplace, a communal living room, and express check-out are also on offer.

Top Westchester hotels deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $193 total per night
$193 total
Aug 3 - Aug 4
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 business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.
Free airport shuttle
Pet friendly
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
$190 nightly
The price is $226 total per night
$226 total
Jul 19 - Jul 20
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
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$295 nightly
The price is $351 total per night
$351 total
Jul 26 - Jul 27
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. There's in-room fitness on site, and concierge services and wedding services are also offered.
Pet friendly
Free WiFi
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
$229 nightly
The price is $269 total per night
$269 total
Aug 7 - Aug 8
Total with taxes and fees
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Free airport shuttle
Pet friendly
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
$210 nightly
The price is $250 total per night
$250 total
Aug 10 - Aug 11
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
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$222 nightly
The price is $264 total per night
$264 total
Aug 9 - Aug 10
Total with taxes and fees
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.
Breakfast included
Free WiFi
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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 $599. 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.