Westchester Vacations from $274

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Your Westchester Vacation

A great way to experience this lively city is with a tailor-made Westchester vacation package. Stay in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our package deals are all about you. A trip to Westchester is a great opportunity to sightsee. Be sure to visit renowned attractions like Brookfield Zoo, Oakbrook Center Mall and Frank Lloyd Wright Historic District. Don't put off your visit to this city any longer. The perfect Westchester vacation is only a few clicks away with Expedia.

The Latest Westchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Zion by IHG

Holiday Inn Express & Suites Zion by IHG

2.5 out of 5
Save 100% on your flight
Price was $392, price is now $274 per person
$274
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (188 reviews)
Staff was Excellent! Room was super clean!

Reviewed on Feb 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,409, price is now $862 per person
$862
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Interesting property in that it is a high rise building of furnished suites with certain floors available as a “hotel”. Coffee shop, gym and lounge are all nice as are the suites. Just know this is not a service oriented hotel experience. No doorman, uniformed person at desk, room or maid service etc.

Reviewed on Mar 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $641, price is now $417 per person
$417
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Riu Chicago was a wonderful hotel. Room was clean and spacious. Breakfast was an added bonus. Within walking distance to many restaurants and stores.

Reviewed on Mar 17, 2026

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Save 100% on your flight
Price was $796, price is now $561 per person
$561
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
9.4/10 Exceptional! (278 reviews)
Everything that i saw and used was great

Reviewed on Mar 16, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was $775, price is now $550 per person
$550
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was clean, comfortable, and well organized The location was perfect, close to restaurants and attractions

Reviewed on Mar 15, 2026

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Discover the most popular places to visit in Westchester

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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
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

What to do in Westchester

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$26
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Westchester

Westchester Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $133 total per night from Apr 1 to Apr 2
$133 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,951 reviews)
The condition of the halls of the hotel and building in general showed its age, but the room had been updated and was clean. The sink and tub drainage was poor. The room was heated very well especially on a cold day. The front desk lady that checked me in seemed in a foul mood but I am sure with ...

Reviewed on Mar 17, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Apr 6 to Apr 7
$179 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,546 reviews)
Riu Chicago was a wonderful hotel. Room was clean and spacious. Breakfast was an added bonus. Within walking distance to many restaurants and stores.

Reviewed on Mar 17, 2026

Hotel Riu Plaza Chicago
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
$130 nightly
The price is $153 total per night from Mar 23 to Mar 24
$153 total
Mar 23 - Mar 24
Total with taxes and fees
8.6/10 Excellent! (5,753 reviews)
Good

Reviewed on Mar 16, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,165 properties in Westchester
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.

Find the Best Westchester Vacation Packages

Westchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
16,700
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District

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Frequently asked questions

How much does a Westchester vacation package cost?
You'll find cheap prices from $274 on Expedia for your Westchester getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Westchester costs.
What are the cheapest months to go to Westchester?
November, December and January are the best times to search for cheap Westchester vacation packages. Opting to travel in quieter periods means you can typically find better prices on accommodations and flights.
How many days is enough for Westchester?
Generally, a handful of days is enough to tick off the top attractions during your Westchester vacation. However, if you want to have more time to relax or take day tours, consider extending your trip.
How to find the best Westchester package deals?
Bagging a cheap Westchester package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Westchester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Westchester vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Westchester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Westchester?
Land incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Westchester escape.
Does Expedia offer Book Now, Pay Later Westchester vacation packages?
Secure your ideal getaway to Westchester with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up bargains before they disappear.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.