Highland Hills Vacations from $389
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Your Highland Hills Vacation
Get ready to experience Highland Hills in your own style with a custom Highland Hills vacation package! Uncovering the best parts of this fascinating city is made easier with a base in a neighborhood such as Clarendon Hills, which is good for golfing, among plenty of other things. Yorktown Shopping Center and Lilacia Park are some of the major attractions to tour during a trip to Highland Hills. Expedia is here to help you escape your routine. Tailor your vacation to Highland Hills to suit your travel style, whatever that may be.
The Latest Highland Hills Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $662, price is now $389 per person
$389
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The hotel was nice, clean and spacious. I lowered my stars because the staff was not friendly to the point of being rude when we checked in and out or asked for assistance with bags. I did not feel welcomed. It was like I was imposing on the staff.
Reviewed on Dec 26, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $743, price is now $431 per person
$431
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,211, price is now $732 per person
$732
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!
Reviewed on Dec 21, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $801, price is now $490 per person
$490
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Where to stay in Highland Hills
Find the best Highland Hills areas and neighborhoods for the activities you enjoy most. Learn more about Highland Hills
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Dec 28 to Dec 29
$80 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (2,431 reviews)
Pros: The room and the lobby were great! The breakfast was tasty and had a variety of things to choose from. The staff was helpful and friendly. Cons: The fitness center equipment was old and somewhat rusty. The motion sensor lights in the bathroom would turn the lights off while I was in the ...
Reviewed on Dec 23, 2025
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $230 total per night from Jan 16 to Jan 17
$230 total
Jan 16 - Jan 17, 2026
Total with taxes and fees
8.2/10 Very Good! (2,188 reviews)
The staff was very helpful.
Reviewed on Dec 23, 2025
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $107 total per night from Jan 8 to Jan 9
$107 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
8.8/10 Excellent! (1,786 reviews)
Yes, everything was perfect.
Reviewed on Dec 21, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.