Deals on vacations and trips to Westchester

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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 $1,200, price is now $717 per person
$717
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,673, price is now $927 per person
$927
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,105, price is now $1,280 per person
$1,280
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This 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, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $750 per person
$750
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,261, price is now $828 per person
$828
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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.

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
$149 nightly
The price is $177 total per night
$177 total
Jul 1 - Jul 2
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
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
$181 nightly
The price is $215 total per night
$215 total
Jul 5 - Jul 6
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/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
$160 nightly
The price is $190 total per night
$190 total
Jul 6 - Jul 7
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night
$154 total
Jul 2 - Jul 3
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
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
$176 nightly
The price is $209 total per night
$209 total
Jul 5 - Jul 6
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.
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
$253 nightly
The price is $297 total per night
$297 total
Jul 3 - Jul 4
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.
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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

An aerial view of a baseball stadium surrounded by urban buildings and streets.

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
A city skyline with a large stadium and marina.

Soldier Field

4.5/5(1,274 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
A Ferris wheel and a carousel at a fairground.

Navy Pier

4.5/5(4,925 reviews)

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 $717. 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

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