Highland Holidays from £846
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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.
Hotel Riu Plaza Chicago
Downtown Chicago
£846
per person
4 Dec - 8 Dec
found 23 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Honestly did not meet expectations. Check in was very fast but overall staff was a cold and not friendly. The only exception were few members at the breakfast restaurant, Maitre D’ and a few of the Bussers. No one offered help with the bags when checking in or out. We were traveling with a toddler and stroller so our hands were pretty full. Everyone seemed very interested in just chatting with other staff members and not connecting with guests at the hotel.
The rooftop seems to be adults only which was not mentioned after we asked reception about checking it out. We tried to go one day and they didn’t help get a high chair for our toddler. I even mentioned getting one from the second floor restaurant which they have and they said no. We ended up going somewhere else nearby instead. My son was not able to get a proper seat for his age. They pointed a a high top table which is absurd.
The hotel has great potential and well located. Unfortunately needs more presence in the hospitality aspect which should be their number one priority. Also note that they charge a $250 fee at checking-in addition to the nightly rate deposit. They claim is for incidentals but is just a way to encourage you spend the money at the hotel restaurant or bar.
Reviewed on 9 Sept 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£1,212
per person
3 Nov - 9 Nov
found 16 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
This hotel was amazing! The room was clean and comfortable, the views were beautiful, and being right on Navy Pier made everything so convenient. I really enjoyed my stay and would definitely come back!
Reviewed on 8 Sept 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
2205 Main St Highland IN
Fully refundableReserve now, pay when you stay
£205
13 Sept - 14 Sept
includes taxes & fees
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
£135
10 Sept - 11 Sept
includes taxes & fees
7/10 Good! (1,017 reviews)
"Internet connection sucked and was not informed of security deposit until we got there"
Reviewed on 8 Sept 2026
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
£78
22 Sept - 23 Sept
includes taxes & fees
7/10 Good! (478 reviews)
"He was a good stay can’t complain"
Reviewed on 8 Sept 2026
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.
What to do in Highland
Chicago Pass: Save up to 50 Percent - Includes 360 CHICAGO
£109
per adult
82% of travellers recommend
Frequently asked questions
How much does a Highland travel package cost?
Discover the best of Highland from as low as £846. 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.
