Westchester Vacations from $437
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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 Chicago North-Evanston by IHG
Downtown Evanston
Price was $629, price is now $437 per person
$437
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,818 reviews)
I love this hotel. Check-in was pleasant, efficient, and the hotel's amenities were nicely highlighted. I was blessed to be granted a room on the south side ofbthe building
Reviewed on Mar 31, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,056, price is now $651 per person
$651
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,394, price is now $940 per person
$940
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,019 reviews)
Wonderful location Nicely updated and appointed rooms. Quiet. Quick elevator. Excellent restaurant on site. Great value for money. Very helpful staff.
Reviewed on Mar 29, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,379, price is now $952 per person
$952
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
Nice staff, clean rooms, however elevator is slow
Reviewed on Apr 2, 2026
Illinois Beach Hotel
Price was $623, price is now $445 per person
$445
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8/10 Very Good! (504 reviews)
Waited 15min to check in. Received an apology along with an explanation of having to do three jobs at once. Shower ceiling had peeling paint with mildew/mold stains. Vanity would not drain. Was relocated to another RM.
Reviewed on Apr 1, 2026
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
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
What to do in Westchester
Chicago Bulls Basketball Game at United Center
$66
per adult
80% of travellers recommend
Westchester Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Apr 5 to Apr 6
$140 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (4,039 reviews)
The toliet was loose in the bathroom
Reviewed on Apr 2, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Apr 5 to Apr 6
$125 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (10,007 reviews)
Good location for where we needed to be in the city. It’s a very dated hotel.
Reviewed on Apr 2, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Apr 12 to Apr 13
$149 total
Apr 12 - Apr 13
Total with taxes and fees
8.6/10 Excellent! (5,809 reviews)
The breakfast changes everyday. My kids enjoyed the stay. Its close to a lot of good places. Front desk staff was very friendly :)
Reviewed on Apr 2, 2026
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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