Highland Hills Vacations from ₩1,569,114

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    Save up to ₩234,741 when you book a flight and hotel together*

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The Latest Highland Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩2,144,860, price is now ₩1,569,114 per person
₩1,569,114
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on Mar 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩2,912,014, price is now ₩1,792,229 per person
₩1,792,229
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Loved my stay her staff was very hospitable and met all our needs. The breakfast buffet was the best I have ever been to.

Reviewed on Mar 9, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩3,689,584, price is now ₩2,680,320 per person
₩2,680,320
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.

Reviewed on Mar 3, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩2,281,394, price is now ₩1,726,360 per person
₩1,726,360
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.

Reviewed on Mar 9, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ₩2,545,408, price is now ₩2,015,210 per person
₩2,015,210
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,993 reviews)
Very clean, small but beautiful updated rooms. Great location. Would stay again. Discounted parking close by.

Reviewed on Mar 9, 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 showing a city

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.

Find hotels in Downtown Chicago

Highland Hills Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is ₩106,799 per night from Mar 12 to Mar 13
₩106,799
₩118,534 total
Mar 12 - Mar 13
includes taxes & fees
9/10 Wonderful! (2,607 reviews)
Every thing was great

Reviewed on Mar 9, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩290,742 per night from Apr 3 to Apr 4
₩290,742
₩341,303 total
Apr 3 - Apr 4
includes taxes & fees
8.4/10 Very Good! (2,231 reviews)
Great!!!

Reviewed on Mar 8, 2026

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩198,941 per night from Apr 3 to Apr 4
₩198,941
₩233,539 total
Apr 3 - Apr 4
includes taxes & fees
8.6/10 Excellent! (1,233 reviews)
This place is always extremely accommodating whenever I’ve had issues flying in or flying out. Have a great shuttle service rooms are always clean and they’re very accommodating. Although the only part that needs help is the bartender I know she was very busy and it’s not always that busy. There ...

Reviewed on Mar 7, 2026

Marriott Chicago O'Hare
See all 3,268 properties in Highland Hills
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.

Frequently asked questions

How much does a Highland Hills vacation package cost?
We make it easy to travel somewhere new, with Highland Hills vacation packages starting from as low as ₩1,569,114. You'll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate escape, why not add a couple of tours and experiences to your travel itinerary?
How do I get a cheap travel package to Highland Hills?
If you love landing a bargain, bundle your bookings into a Highland Hills vacation package. Whether you're chasing hotels, flights, rental cars or day tours, you can book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 hotel options worldwide to choose from. Fly with who you prefer, stay wherever you like and save a pretty penny — now that's the perfect vacation!
Where should I stay in Highland Hills?
There's so much to see in Highland Hills, so spend your nights close to its top attractions and treat yourself to more time sightseeing. Yorktown Shopping Center is one spot to put on your must-see list.
What are the top hotels in Highland Hills?
Sonesta ES Suites Chicago - Lombard and SureStay Plus Hotel by Best Western Chicago Lombard are a couple of the most sought-after properties in Highland Hills. Why not have a look at the facilities and rates at each and then decide?
How far in advance should I book my Highland Hills vacation?
While not all air carriers release ticket prices early, you can usually look up international fares on Expedia up to 12 months in advance. This is when you'll score some incredible bargains. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the cheapest prices emerge only weeks before departure.
What does an Expedia Highland Hills travel package include?
Expedia has all you need to arrange your Highland Hills trip, but what your package looks like is your choice. Select from any combination of flights, hotels and rental cars. In search of some experiences or tours to keep you busy? Once you've made your booking, you can add them on too. No matter your style or budget, there's a deal to suit your needs.
What should I know before booking a Highland Hills travel package?
Bundling your bookings into a Highland Hills vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Highland Hills Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Highland Hills vacation package?
Don't worry if you're rethinking your Highland Hills vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realize life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in Highland Hills

Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Beautiful autumn colors surround modern architecture in Millennium Park, Chicago during a sunny day

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.