Westchester Vacation Packages

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Flight and hotel packages to Westchester

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The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, 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 gym, bar/lounge, and coffee shop.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
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 laundry facilities.

Top Westchester hotel 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
The price is $167 per night
$167
per night
May 27 - May 28
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.
Breakfast available
Parking available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $149 per night
$149
per night
May 27 - May 28
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
Parking available
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $125 per night
$125
per night
May 29 - May 30
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-in, and valet parking.
Pet friendly
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $180 per night
$180
per night
May 29 - May 30
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
Parking available
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is $149 per night
$149
per night
May 27 - May 28
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.
Pet friendly
Breakfast included
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $122 per night
$122
per night
May 27 - May 28
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Parking available
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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.

Popular places to visit in Westchester

Image for Wrigley Field

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.

Wrigley Field
Image for Six Flags Great America

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.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

Frequently asked questions

How much are vacation packages to Westchester?
You’ll be pleasantly surprised — you can unwind in Westchester for a mere $317. Let Travelocity save you time and stress with our excellent vacation packages. With flights, hotels and tours all ready to go at our one-stop shop, what’s holding you back?
How long should my Westchester vacation be?
Many travelers choose to spend about 2 nights in Westchester. But what’s right for them mightn’t be right for you. Whether you prefer to stay for a few days or a few weeks, you’ll love exploring all the wonderful things that this destination has to offer.
Where can I get the best vacation package deals for Westchester?
It’s hard to look past Travelocity when it comes to putting together your Westchester package deal. There are as many as 400 airlines and 1,000,000 worldwide properties to choose from. Book your vacation now and get ready to tick another amazing place off your must-visit list.
Why should I book my Westchester vacation package with Travelocity?
Because we believe in crafting stress-free vacation experiences. From hotels and flights to car rentals and activities, our packages make it a breeze to save. Our customer support team is available 24/7 to ensure you’ll never roam alone. We also have an amazing Price Match Guarantee, so you can secure your trip knowing you’ve landed the best deal around.
Can I save money on my Westchester car rental if I combine it with a hotel or flight?
You most certainly can — bundle your flight, hotel and car into a Westchester vacation package and you can save a ton. With so much to discover in and around Westchester, having your own ride will make exploring easy. Once you’ve settled into the driver’s seat, crank up the music and cruise toward Six Flags Great America, a top attraction around 35 mi from Westchester.
What is the best time of year to go to Westchester?
If a tight budget is what’s driving your travel plans, you’ll score the best prices in . is usually the most expensive time of year. Most visitors head here around April, May and June. If you’d prefer to avoid the crowds, visit during November, December and January.
Which airport is best for Westchester?
Many visitors 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?
If you’re after somewhere to base yourself, check out the Four Points by Sheraton Chicago Westchester/Oak Brook. It’s the top pick for many visitors.