Highland Hills Holidays

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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
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
8/10 Very Good! (1,023 reviews)
Just too average for the price. If it was less money and same details, I’d have a little more appreciation for it.

Reviewed on 20 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
I loved our stay. The view was unbelievable. The tub was the only concern, it was leaking the water out from the drain area so i had to use more water. That was not a tragedy but just so you guys know it could use a small fix.

Reviewed on 22 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (977 reviews)
The hotel was absolutely perfect for our quick weekend getaway. It was super comfortable, clean and safe. The staff was wonderful!

Reviewed on 19 May 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
EXCEPTIONAL SERVICE!!

Reviewed on 21 May 2024

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 featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Top hotels in Highland Hills

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 HK$702 per night from 26 May to 27 May
HK$702
per night
26 May - 27 May
8.6/10 Excellent! (1,531 reviews)
"Very good"

Reviewed on 20 May 2024

SureStay Plus Hotel by Best Western Chicago Lombard
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3.5 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is HK$1,319 per night from 27 May to 28 May
HK$1,319
per night
27 May - 28 May
8.6/10 Excellent! (1,009 reviews)
"Great property"

Reviewed on 20 May 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Best Western At O'Hare
Best Western At O'Hare
2.5 out of 5
10300 W Higgins Road, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is HK$856 per night from 28 May to 29 May
HK$856
per night
28 May - 29 May
7.2/10 Good! (1,836 reviews)
"This stay was everything that I needed after returning back to the States from a 3-week trip to Europe. The hotel shuttle was convenient and faster than what I read in other reviews. My bed was very comfortable and the breakfast was good. They even had room service, but after 20 hours of traveling, ..."

Reviewed on 22 May 2024

Best Western At O'Hare
See all 2,753 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 HK$3,711. 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 holiday 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 holiday!
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 holiday?
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 holiday package is the most convenient way to organise 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 holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our holiday 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.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

Things to do

Image for Skyline Lake Tour

Skyline Lake Tour

HK$294
Per adult
92% of travellers recommend
Skyline Lake Tour
Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

HK$1,473
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
See all activities in Chicago

More trip options

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