Highland Hills Vacation Packages

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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.

Top Holiday Package Deals in Highland Hills

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Save 100% on your flight
per person
Feb. 15 - Feb. 22
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
It was very nice peaceful, not much to worry about

Reviewed on Dec. 23, 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb. 15 - Feb. 22
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,004 reviews)
Great hotel & even greater area. The waterfront view was very nice to wake up to.

Reviewed on Dec. 23, 2024

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 8 - Mar. 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
8.4/10 Very Good! (1,501 reviews)
For the holidays, it was well decorated. We had a nice view of the lake from our room. Conveniently located and quiet.

Reviewed on Dec. 26, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 8 - Mar. 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (277 reviews)
I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location

Reviewed on Dec. 7, 2024

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 8 - Mar. 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
8.8/10 Excellent! (1,923 reviews)
Everything was great

Reviewed on Dec. 26, 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 showing a city

Downtown Chicago

5 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 Michigan Avenue and Millennium Park 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

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 CA $104 per night from Jan. 22 to Jan. 23
CA $104
CA $116 total
includes taxes & fees
Jan 22 - Jan 23, 2025
8.8/10 Excellent! (1,894 reviews)
"Nice stay overall, room starting to get run down but nice area and served our needs. Staff was very friendly!"

Reviewed on Dec. 25, 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 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is CA $159 per night from Jan. 7 to Jan. 8
CA $159
CA $187 total
includes taxes & fees
Jan 7 - Jan 8, 2025
8.6/10 Excellent! (1,290 reviews)
"I loved the pool, it was very big and spaceous and the water temp was perfect. The room it self was also nice. would def recommend coming back."

Reviewed on Dec. 22, 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
3 out of 5
1 S Franklin Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Jan. 6 to Jan. 7
CA $142
CA $167 total
includes taxes & fees
Jan 6 - Jan 7, 2025
8.6/10 Excellent! (2,196 reviews)
"Great location, breakfast included. I liked that you needed to use a keycard to use the elevator to prevent people who were not staying at the hotel from getting to our floor."

Reviewed on Dec. 25, 2024

La Quinta Inn & Suites by Wyndham Chicago Downtown
See all 2,773 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 CA $841. 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

Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 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.

Michigan Avenue
Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
McCormick Place

McCormick Place

4.5/5(141 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

Flyover in Chicago

Flyover in Chicago

CA $54
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $70
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $64
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.