Highland Hills Vacations from $561
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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 Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $861, price is now $561 per person
$561
per person
Aug 6 - Aug 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
The room, the location, the amenities it comes with it’s fair for the price
Reviewed on Jun 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,768, price is now $1,124 per person
$1,124
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Liked the key activation for the lighting
Reviewed on Jun 30, 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $1,146, price is now $750 per person
$750
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,941 reviews)
Our room was a great size, comfortable and the air conditioning worked great. My only complaint is that the bathroom is a little dated and crowded but otherwise we had no problems. The hotel’s proximity to magnificent mile, old town and Gold Coast is great. We walked almost everywhere. The staff was very helpful and accommodating.
Reviewed on Jun 29, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,363, price is now $927 per person
$927
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good.
Reviewed on Jun 30, 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
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
$80 nightly
The price is $89 total per night from Jul 1 to Jul 2
$89 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (2,834 reviews)
"The breakfast choices we mid at best."
Reviewed on Jun 30, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jul 20 to Jul 21
$154 total
Jul 20 - Jul 21
Total with taxes and fees
8.8/10 Excellent! (2,755 reviews)
"They over charge your card and then can’t tell what the charge is for or make something up. When we got there they gave us a dirty room and we had to call to get out room changed not a upgrade but whatever."
Reviewed on Jun 30, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$240 nightly
The price is $282 total per night from Jul 4 to Jul 5
$282 total
Jul 4 - Jul 5
Total with taxes and fees
8.4/10 Very Good! (2,331 reviews)
"Staff were really helpful and sweet during check in. During checkout I was told there are no shuttles to take me to my terminal in quite a short and ubrupt manner. But to be honest the price is ridiculous for the outdated hotel. Seems like they think they can charge Hilton prices for what looks like ..."
Reviewed on Jun 30, 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
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.