Illinois may have travel restrictions in place, including self-quarantine, due to COVID-19.

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Highland Hills Vacation Packages

Choose one or more items to build your trip:

Highland Hills Vacation: Coronavirus Information

Most Highland Hills hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Highland Hills trip, please visit our Coronavirus Information page (opens in new window).

Top Highland Hills Flight + Hotel Deals

The Langham, Chicago

The Langham, Chicago

5 out of 5
River North
Save 100% on your flight$690

$535

per person
Mar 16 - Mar 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
4.9/5Exceptional! (1,172 reviews)

"The best hotel to stay in Chicago, super hood services and everything clean.…"

Reviewed on Dec 31, 2020

Wingate by Wyndham Arlington Heights

Wingate by Wyndham Arlington Heights

3 out of 5
Save 100% on your flight$362

$313

per person
Mar 30 - Apr 6
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
4/5Very Good! (1,000 reviews)

"The initial night checking in the front desk staff was incredibly helpful and friendly. I had to unexpectedly checkin to a hotel and her kindness turned my night around. The room was very clean and comfortable, our amenities were very useful. I understood the kitchen was closed due to covid-19 however we were very disappointed with a granola bar and water that was served for breakfast. We at least expected oatmeal or a prepacked meal we could warm up in the microwave.…"

Reviewed on Jan 7, 2021

Comfort Suites Schiller Park - Chicago O'Hare Airport

Comfort Suites Schiller Park - Chicago O'Hare Airport

3 out of 5
Save 100% on your flight$437

$388

per person
Mar 30 - Apr 6
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
4.2/5Very Good! (519 reviews)

"My Family and i enjoyed overall in these presedented times that they were actually serving hot breakfast that really made my kids really happy lol .the staff was great ,accurate and very efficient to say very humble and respectful. The price was a perfect fit to my budget i couldn't ask for more big thank you and shout to the comfort suite's in shiller park Illinoi it was an awesome stay .o and before i forget the rooms were super clean beds very comfortable as well 👍💪🙏…"

Reviewed on Jan 5, 2021

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3.5 out of 5
Streeterville
Save 100% on your flight$308

$276

per person
Mar 16 - Mar 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
4.4/5Excellent! (1,000 reviews)

"This was a great stay, just like every time we come.…"

Reviewed on Jan 4, 2021

Renaissance Chicago O'Hare Suites Hotel

Renaissance Chicago O'Hare Suites Hotel

4 out of 5
O'Hare
$314

$284

per person
Feb 26 - Mar 1
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
4.1/5Very Good! (1,001 reviews)

"Beautiful hotel! Loved the rooms. The Starbucks downstairs didn’t taste anything like the regular locations (I been a regular for 14 years) but overall great stay! Will visit again!”…"

Reviewed on Dec 20, 2020

2021 Highland Hills vacation deals

Found Hotel Chicago River North

Found Hotel Chicago River North

3 out of 5
River North
$389

$206

per person
Jan 20 - Jan 22
Roundtrip flight included
Seattle (SEA) to Chicago (CHI)
4.3/5Excellent! (840 reviews)

"Everything was Beautiful and the staff was great .…"

Reviewed on Oct 25, 2020

The Langham, Chicago

The Langham, Chicago

5 out of 5
River North
Save 100% on your flight$690

$535

per person
Mar 16 - Mar 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
4.9/5Exceptional! (1,172 reviews)

"The best hotel to stay in Chicago, super hood services and everything clean.…"

Reviewed on Dec 31, 2020

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Streeterville
$644

$555

per person
Mar 19 - Mar 25
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
4.6/5Wonderful! (1,524 reviews)

"Spacious room... Good views...King size bed was sooo comfortable…"

Reviewed on Sep 14, 2020

Omni Chicago Suites - Magnificent Mile

Omni Chicago Suites - Magnificent Mile

4.5 out of 5
Magnificent Mile
$725

$628

per person
Mar 19 - Mar 25
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
4.5/5Wonderful! (1,593 reviews)

"It was very clean! Very comforting as well and we had a good stay.…"

Reviewed on Mar 24, 2020

Sheraton Grand Chicago

Sheraton Grand Chicago

4 out of 5
Streeterville
$762

$660

per person
Mar 19 - Mar 25
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
4.2/5Very Good! (1,443 reviews)

"Great location. Next to the river, shopping center and the cinema.…"

Reviewed on Nov 30, 2020

Top Hotels in Highland Hills

Extended Stay America - Chicago - Lombard - Yorktown Center
Extended Stay America - Chicago - Lombard - Yorktown Center
2.5 out of 5
260 E 22nd St, Lombard, IL
Free CancellationReserve now, pay when you stay
The price is $65 per night from Jan 19 to Jan 20
3.4/5 (489 reviews)
nice hotel overall.

"The service desk staff are excellent, I was not happy with the breakfast that was provided during out stay. I wish they will do better on that. The room we stayed in was dirty, there were wrappers of granola bar that was left behind the entrance door. Other than that, everything looks good."…"

Reviewed on Mar 19, 2020

Extended Stay America - Chicago - Lombard - Yorktown Center
Aloft Chicago O'Hare
Aloft Chicago O'Hare
3 out of 5
9700 Balmoral Ave, Rosemont, IL
Free CancellationReserve now, pay when you stay
The price is $71 per night from Jan 26 to Jan 27
4.1/5Very Good! (983 reviews)

"love my stay. clean and friendly staff. will be back!"…"

Reviewed on Jan 17, 2021

Aloft Chicago O'Hare
Hyatt Place Chicago/O'Hare Airport
Hyatt Place Chicago/O'Hare Airport
3 out of 5
6810 Mannheim Rd, Rosemont, IL
Free Cancellation
The price is $79 per night from Jan 19 to Jan 20
4.3/5Excellent! (1,945 reviews)

"Front desk staff was excellent. Very helpful with delivery food suggestions."…"

Reviewed on Jan 13, 2021

Hyatt Place Chicago/O'Hare Airport
See all 1384 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.
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Top things to do in Highland Hills

Image for Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS: Admission to Top 5 Chicago Attractions

$109
Per adult
94% of travellers recommend
Chicago CityPASS: Admission to Top 5 Chicago Attractions
Image for Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

$83
Per adult
80% of travellers recommend
Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions
See all activities in Highland Hills

What are the advantages of a road trip to Highland Hills?

There’s nothing quite like a Highland Hills road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Highland Hills or bundle your hotels with car rentals to save even more. With our Highland Hills packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.  

How to plan a road trip to Highland Hills?

Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals in Highland Hills and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.  

What to do on a road trip to Highland Hills?

When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Highland Hills. You can book all the road trip activities on your Highland Hills wishlist, and even plan activities along your route as well.  

How to rent a car for a road trip?

For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Highland Hills. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.

Frequently asked questions

How much does a Highland Hills vacation package cost?
The most affordable Highland Hills package is $206, so your dream getaway can become a reality — without spending an arm and a leg. Bundle flights, hotels, car rentals and more to customize a package that fits you.
If I'm not able to travel, can I cancel my Highland Hills vacation package?
Because we know life is full of surprises, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you’ve booked your Highland Hills vacation package in the last 24 hours, you may be able to cancel or change it with no penalties. Your hotel, airline or car rental company may charge a fee if your booking is older than that.
How do I get a cheap travel package to Highland Hills?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into a Highland Hills vacation package and save up to $583. Score even more deals when you include extras such as tours or experiences to your booking. But here’s the most impressive part. You have the flexibility to put together your vacation your own way. We offer more than 550 airlines and 1,000,000 hotels globally, so that everyone has a chance to travel and fulfill those vacation dreams.
What are the top hotels in Highland Hills?
Whether you aim to stay for a night or a week in Highland Hills, you’ll get a great night’s sleep at Extended Stay America - Chicago - Lombard - Yorktown Center. This place is a favorite with lots of travelers.
When is the best time of year to visit Highland Hills?
If your definition of “best” means when you’ll land the best deals, pack your bags and head for Highland Hills in . In contrast, is the most expensive month to plan a getaway. Peak season falls in and is a thrilling time to visit — if you don’t mind rubbing elbows with the crowds. is usually a quieter time of the year.
How far in advance should I book my Highland Hills vacation?
Travelers can normally browse international airfares on Expedia up to 12 months prior to departure. Booking at the last minute? With a stroke of luck, there’s a still a chance you can purchase a cheap ticket just weeks before your journey.
What does an Expedia Highland Hills travel package include?
It all comes down to what sort of trip you have in mind. Highland Hills vacation deals can include flights, hotels and car rentals. You can mix and match to create the travel package that suits your needs. You can also add on activities and experiences after you’ve booked to get even bigger discounts.
What should I know before booking a Highland Hills travel package?
You’ll score excellent savings when you bundle your flights, hotels and rental cars into a travel package. Plus, booking everything together will make your trip planning easier. So why waste time or money? Whether you’re putting together a luxury city stay with your love or a budget family adventure, have a look at our package deals today.
Does Expedia offer Book Now, Pay Later Highland Hills vacation packages?
Pay the total cost of your package booking when you book or split it into numerous installments — it’s totally up to you. Every traveler has their own set of financial circumstances. That’s why Expedia has teamed up with online lender Affirm to provide a Book Now, Pay Later option for all package bookings.
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 globally. Our packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.

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