Highland Hills Vacations from $264
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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 $428, price is now $264 per person
$264
per person
Apr 9 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Muy buen hotel y la ubicación excelente
Reviewed on Jan 14, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $794, price is now $462 per person
$462
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026
Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
Save 100% on your flight
Price was $564, price is now $348 per person
$348
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars.
Reviewed on Jan 12, 2026
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Save 100% on your flight
Price was $673, price is now $416 per person
$416
per person
Apr 8 - Apr 11
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
8.4/10 Very Good! (999 reviews)
Enjoyed the room. The staff could use a hug not the friendliest. The games our outdated. Seen many guest besides me decide to go play at the other area casino
Reviewed on Jan 1, 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was $922, price is now $572 per person
$572
per person
Mar 23 - Mar 26
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast
Reviewed on Jan 4, 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
$72 nightly
The price is $80 total per night from Jan 15 to Jan 16
$80 total
Jan 15 - Jan 16
Total with taxes and fees
9/10 Wonderful! (2,498 reviews)
Breakfast was great (pancakes, waffles, eggs cereal, toast, sausage or bacon etc). Staff was great, I see the same faces on my visits. Restaurants expensive to non expensive in the area. Shopping center is nearby. I can not say enough nice things about this place.
Reviewed on Jan 12, 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
Fully refundable
$112 nightly
The price is $131 total per night from Jan 29 to Jan 30
$131 total
Jan 29 - Jan 30
Total with taxes and fees
8.8/10 Excellent! (2,112 reviews)
Clean room, great location downtown, great amenities.
Reviewed on Jan 14, 2026
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 Feb 6 to Feb 7
$230 total
Feb 6 - Feb 7
Total with taxes and fees
8.2/10 Very Good! (2,180 reviews)
Stayed prior to flight, clean, quiet room!
Reviewed on Jan 13, 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.
Discover the most popular places to visit in Highland Hills
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.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.