Highland Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Highland Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Beautiful hotel, quiet clean spacious rooms! Breakfast buffett to die for. Close to museums and Metro.

Reviewed on 24 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (931 reviews)
We had multiple issues with the locks on our door.

Reviewed on 24 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.

Reviewed on 20 Nov,2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Andy at the front desk was amazing and so professional! Just based on the service he provided, I will be back! Hotel is in an excellent location as well! Would definitely recommend!

Reviewed on 25 Nov,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Highland

Hilton Chicago/Oak Lawn
Hilton Chicago/Oak Lawn
3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is S$177 per night from 22 Dec to 23 Dec
S$177
includes taxes & fees
22 Dec - 23 Dec
7.6/10 Good! (1,012 reviews)
"Jocelyn the front desk clerk was so nice and made sure we had everything that was needed."

Reviewed on 23 Nov,2024

Hilton Chicago/Oak Lawn
DoubleTree by Hilton Chicago - Alsip
DoubleTree by Hilton Chicago - Alsip
4 out of 5
5000 W 127th St, Alsip, IL
Fully refundableReserve now, pay when you stay
The price is S$169 per night from 1 Dec to 2 Dec
S$169
includes taxes & fees
1 Dec - 2 Dec
8/10 Very Good! (1,003 reviews)
"Clean & quiet. Overall a good stay"

Reviewed on 23 Nov,2024

DoubleTree by Hilton Chicago - Alsip
Hyatt Place Chicago-South/University Medical Center
Hyatt Place Chicago-South/University Medical Center
3 out of 5
5225 S Harper Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$240 per night from 9 Dec to 10 Dec
S$240
includes taxes & fees
9 Dec - 10 Dec
8.6/10 Excellent! (1,001 reviews)
"Nice place"

Reviewed on 21 Nov,2024

Hyatt Place Chicago-South/University Medical Center
See all 719 properties in Highland
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 holiday package cost?
From as little as S$757. Yes, you read that correctly. Our Highland packages are the easiest way to make your dollar go further. Combine your preferred hotels, flights and car rentals and get out and explore this fabulous destination.
How do I get a cheap travel package to Highland?
Browse and lock in everything all in one place with our Highland holiday packages. We have incredible bargains on hotels, flights and more that’ll keep your pocket happy and your sense of adventure alive. And, with more than 550 airlines and 1,000,000 properties worldwide to choose from, you have countless opportunities to mix and match as you want.
Where should I stay in Highland?
Stay where the action happens. Many travellers favor hotels in the vicinity of popular attractions, such as Hard Rock Casino Northern Indiana, Purdue University Northwest and South Shore Convention and Visitors Authority.
How far in advance should I book my Highland holiday?
Browse Expedia to compare international fares as soon as possible. You can generally purchase a ticket up to a year in advance. If you don’t see your preferred air carrier, or you’re booking late, don’t despair. Low prices to Highland sometimes occur a few weeks before departure.
What does an Expedia Highland travel package include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply select your preferred bundle and gain access to great discounts. Once you’ve made your booking, add on a couple of tours and experiences and watch your savings grow. When it comes to creating your Highland trip, you’re the boss!
What should I know before booking a Highland travel package?
When you book your flights, hotels and car rentals together, you’ll be rewarded with awesome discounts. Whether you’re planning a beach break in a villa or want to stay in an upscale city hotel, Expedia will help make it happen.
Can I choose my airline with a Highland Expedia holiday package?
Expedia offers access to more than 550 partner airlines worldwide, so you sure can! Just select your preferred carrier and put together your ideal Highland escape.
If I'm not able to travel, can I cancel my Highland holiday package?
Yes you can, and we’ll help you every step of the way. You may be able to cancel or change your Highland holiday package for free if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your holiday, look up our Customer Service Portal for further information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.