Deals on vacations and trips to Westchester

Save when you book Westchester package deals

Choose two or more items and save on your trip:

Top Westchester hotels deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $105 total per night
$105 total
Jan 5 - Jan 6, 2026
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
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $179 total per night
$179 total
Jan 3 - Jan 4, 2026
Total with 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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Pool
Spa
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $149 total per night
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 library, express check-in, and express check-out are also on offer.
Free WiFi
Air conditioning
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $103 total per night
$103 total
Jan 24 - Jan 25, 2026
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. A snack bar/deli, express check-in, and express check-out are also on offer.
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
$147 nightly
The price is $173 total per night
$173 total
Jan 3 - Jan 4, 2026
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
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $110 total per night
$110 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Spa
Free WiFi
Don't see what you're looking for?
See all available properties in Westchester
View all properties
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

Magnificent Mile - River North showing night scenes, a city and signage

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.

Michigan Avenue
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Frequently asked questions

How much are vacation packages to Westchester?
Travelocity offers package deals to Westchester, including hotels and flights, starting from an impressive . 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