Highland Holidays from £929

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Your Highland Holiday

Lock in a Highland holiday package and get set to experience this exciting city the stress-free way. Consider spending some time in the neighbourhood of East Side, which is great for nature and walking. Fill your days with visits to Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Centre, some of the things you just have to see during a trip to Highland. Check out Expedia's wide range of travel options and book your perfect holiday to Highland now.

The Latest Highland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on 10 Jan 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The staff are thoughtful and provide the best service. While I was there, I was already planning to come back and stay there again!

Reviewed on 24 Apr 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on 15 Apr 2024

Hotel Arista

Hotel Arista

4.5 out of 5
per person
1 Jun - 5 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
It was a really nice stay. we had the king size bed room. It’s a really nice hotel. The only reason I took one star off was because the bed was very firm and about knee-high and the pillows were also very hard. I don’t know if they have rooms that have softer beds, but for that reason, I would never stay there again.

Reviewed on 26 Apr 2024

Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
Bedford Park
per person
1 Jun - 5 Jun
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Front desk staff were extremely nice and helpful. Very convenient to Midway airport.

Reviewed on 26 Apr 2024

The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Love the excelente service, view and staff that was so helpful!!

Reviewed on 19 Apr 2024

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

Our pick of the best Highland Hotel Deals

Econo Lodge
Econo Lodge
2 out of 5
17301 S Halsted St, Building B, South Holland, IL
Stay at this hotel in South Holland. Enjoy free WiFi, free parking and room service. Popular attractions Midwest Carvers Museum and South Holland Village Hall ...
4.6/10 (351 reviews)
"Didn’t like having a bouncer knock on my door at 11 on the dot to remind me of check out"

Reviewed on 5 Apr 2024

Econo Lodge
Holiday Inn Chicago Matteson Conf Center, an IHG Hotel
Holiday Inn Chicago Matteson Conf Center, an IHG Hotel
3 out of 5
500 Holiday Plaza Dr, Matteson, IL
Stay at this business-friendly hotel in Matteson. Enjoy free WiFi, free parking and breakfast. Our guests praise the helpful staff in their reviews. Popular ...
7.2/10 Good! (1,000 reviews)
"The staff is friendly, it’s really nice and clean"

Reviewed on 22 Apr 2024

Holiday Inn Chicago Matteson Conf Center, an IHG Hotel
Hyatt Place Chicago-South/University Medical Center
Hyatt Place Chicago-South/University Medical Center
3 out of 5
5225 S Harper Ave, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi and a free local area shuttle. Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,002 reviews)
"Nice"

Reviewed on 22 Apr 2024

Hyatt Place Chicago-South/University Medical Center
See all 720 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

Frequently asked questions

How much does a Highland travel package cost?
Discover the best of Highland from as low as £929. 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.