Highland Holidays from £712

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Your Highland Holiday

Spend less time travel planning and more time having exciting adventures with a Highland holiday package. The neighbourhood of East Side, which is good for nature and walking, makes an excellent base for your city break. Like to get out and explore? Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Centre are three of the leading places to visit during your trip to Highland. Don't delay your visit to this destination any longer. Your ultimate Highland holiday is only a few clicks away with Expedia.

Top Highland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £874, price is now £712 per person
£712
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,789, price is now £1,319 per person
£1,319
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
i love it

Reviewed on 10 Nov 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,006, price is now £804 per person
£804
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Very good

Reviewed on 11 Nov 2026

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was £1,413, price is now £1,143 per person
£1,143
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The hotel lobby and rooftop are nice but the rooms are okay. We had 3 rooms and the shower pressure was terrible in all. The king room felt small so we switched to 2 queens which was much better. The service was so good though and it’s attached to a mall. It was good overall but probably won’t stay here again.

Reviewed on 29 Oct 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,008, price is now £819 per person
£819
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
Everything was perfect

Reviewed on 11 Nov 2026

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
22,900
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Whihala Beach, Mascot Hall Of Fame and Lake Street Beach

Top hotels in Highland

The Cardinal Hotel

The Cardinal Hotel

3 out of 5
2205 Main St Highland IN
Fully refundableReserve now, pay when you stay
The price is £195 per night from 15 Nov to 16 Nov
£195
15 Nov - 16 Nov
includes taxes & fees
The Cardinal Hotel
Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel

4.5 out of 5
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is £115 per night from 1 Dec to 2 Dec
£115
1 Dec - 2 Dec
includes taxes & fees
9.4/10 Exceptional! (871 reviews)
"In an absolutely bombed out area, but the hotel is beautiful and very secure."

Reviewed on 11 Nov 2026

Wind Creek Chicago Southland Casino and Hotel
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 £96 per night from 22 Nov to 23 Nov
£96
22 Nov - 23 Nov
includes taxes & fees
DoubleTree by Hilton Chicago - Alsip
See all 943 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in Highland

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

Chicago Pass: Save up to 50 Percent - Includes 360 CHICAGO

£111
per adult
82% of travellers recommend
Chicago Pass: Save up to 50 Percent - Includes 360 CHICAGO
See all activities in Highland

Frequently asked questions

How much does a Highland travel package cost?
Discover the best of Highland from as low as £712. We offer a great selection of flights, hotels and rental cars to suit every budget and style. Pick up even better deals when you add a few activities or tours to your travel package.
If I'm not able to travel, can I cancel my Highland travel package?
Don't stress if you're rethinking your Highland travel 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 for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that life can occasionally throw a spanner in the travel works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we're here to help.
How do I get a cheap travel package to Highland?
If you love getting a great deal, combine your bookings into a Highland travel package. Whether you're looking for flights, hotels, rental cars or day tours, you can book them all in one place. You'll have lots of choice at your fingertips as well. Expedia has over 550 airlines and 1,000,000 hotel options around the globe to pick from. Fly with who you prefer, check in where you like and save some cash — now that's the ideal escape!
Does Expedia offer Book Now, Pay Later Highland holidays?
Expedia has partnered with online lender Klarna to make booking your next trip easier on your hip pocket. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that fits into your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Highland?
A holiday in Highland wouldn't be complete without checking out Hard Rock Casino Northern Indiana, Purdue University Northwest and Theatre at the Centre. Spend your evenings close to these popular attractions and make sightseeing a breeze.
What are the top hotels in Highland?
Get your escape off to an excellent start by booking a stay at Sheraton Indianapolis Hotel at Keystone Crossing. It's one of most sought-after hotels in Highland. Another welcoming option is Hilton Fort Wayne at the Grand Wayne Convention Centre.
How far in advance should I book my Highland holiday?
While not all airlines release ticket prices early, customers are usually able to look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some fantastic deals. If you're booking at the last minute, there's a chance you could get lucky. Low prices sometimes appear just weeks prior to departure.
What does an Expedia Highland travel package include?
With Expedia, you can select any combination of hotels, car rentals and flights to create your perfect Highland travel package. Once you've made your booking, you can add on the fun stuff like tours and experiences. Don't forget, the more you bundle, the more deals you'll score!
What should I know before booking a Highland travel package?
Get set to save with an Expedia travel package. Combine your airfares, rental cars and hotels and score great discounts. Hotels aren't your only option, however. Book with us and select from beachside condos, rural cottages and even glamping tents!
Can I choose my airline with a Highland Expedia travel package?
Definitely. Expedia has more than 550 airline partners to choose from across the world. With so many choices, finding the right carrier to get you to Highland will be a breeze.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.