Highland Hills Vacations from $308
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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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $492, price is now $308 per person
$308
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.
Reviewed on Oct 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $892, price is now $521 per person
$521
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Great location, nice rooms, nice rooftop bar and large breakfast buffet included.
Reviewed on Oct 28, 2026
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
4 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
$97 nightly
The price is $107 total per night from Nov 5 to Nov 6
$107 total
Nov 5 - Nov 6
Total with taxes and fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $215 total per night from Nov 28 to Nov 29
$215 total
Nov 28 - Nov 29
Total with taxes and fees
8.6/10 Excellent! (2,584 reviews)
"This hotel was horrible. All services are closed at midnight and I landed at 12:30 a.m. No bar or no mini store to buy stuff. My room was okay but super stuffy, moldy smell, hot, the AC was not on. The sheets were itchy. The shower in the morning had COLD water, no kidding. I will never stay at this ..."
Reviewed on Oct 29, 2026
Hyatt Place Chicago/Downtown - The Loop
28 North Franklin Street Chicago IL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $140 total per night from Nov 23 to Nov 24
$140 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,684 reviews)
"Great"
Reviewed on Oct 28, 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.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.