Westchester Vacations from $494
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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.
The French Country Inn Lake Geneva
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (126 reviews)
The views are great in this historic Inn. Layed back but still classy. Away from the crowds but great dining that adds some fun. Could use a few room convinces and amenities like a working coffee and micro.
Reviewed on Jun 29, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
So easy to access the beautiful city, lots of restaurants...so nice
Reviewed on Jul 15, 2025
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View all tripsDiscover the most popular places to visit in Westchester
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.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Michigan Avenue
4.5/5(332 reviews)
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.
What to do in Westchester
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
94% of travellers recommend
Westchester Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $205 total per night from Aug 7 to Aug 8
$205 total
Aug 7 - Aug 8
Total includes taxes and fees
7.8/10 Good! (8,972 reviews)
"The area was pretty nice, and hotel was remodeled in some areas. Didnt like the bathroom was dirty the bucket wasnt empty when we arrived"
Reviewed on Jul 15, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
$251 nightly
The price is $289 total per night from Aug 8 to Aug 9
$289 total
Aug 8 - Aug 9
Total includes taxes and fees
9/10 Wonderful! (2,047 reviews)
"Great. Just hard to get parked to get into hotel due to busy location."
Reviewed on Jul 15, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $172 total per night from Aug 10 to Aug 11
$172 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,444 reviews)
"clean...close to attractions.."
Reviewed on Jul 14, 2025
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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