Westchester Vacations from $382
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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
Price was $855, price is now $382 per person
$382
per person
Dec 16 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (146 reviews)
The rooms are cozy with deck space overlooking Lake Como and the Getaway restaurant was on the property with a beautiful terraced patio. The food and service were great!
Reviewed on Oct 16, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,312, price is now $748 per person
$748
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Staff friendly and convenient. However, a bit loud, like we were on the sidewalk hearing music, cars and trains. Room was very minimal and a bit stark. Most like a dorm room/hostel. Very low lighting, fine except to try to read at night.
Reviewed on Oct 15, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $715, price is now $413 per person
$413
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on Oct 4, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,123, price is now $659 per person
$659
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.
Reviewed on Oct 15, 2025
Don't see what you're looking for?
See all available trips from Columbus to Westchester
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.
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.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Westchester
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Westchester Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (9,429 reviews)
"Beautiful view and clean room, held my bags for the day while I had some business before I left the city"
Reviewed on Oct 16, 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Nov 10 to Nov 11
$100 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,480 reviews)
"I was there for the marathon and had a shared female room — the three others ended up being runners too, which was great. The location is fun and lively, but my room on the 9th floor was quiet. The staff were really nice — one of them even lent me his luck for the locker and gave me a card for the ..."
Reviewed on Oct 16, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $131 total per night from Nov 16 to Nov 17
$131 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,118 reviews)
"Clean, quiet, safe!"
Reviewed on Oct 15, 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.
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
