Highland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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 easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Highland
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
€1,257
per person
26 Oct - 30 Oct
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The hotel was so amazing for us. Staff was accommodating and helped us immensely. The restaurant for breakfast and the roof top wil keep you coming back. We will try to stay there as much as we can while in Chicago.. Lester and Luis at the restaurants need a bonus. They kept the breakfast crowd well organized.
Reviewed on 4 Sept 2026
Arlo Chicago
Downtown Chicago
€874
per person
18 Nov - 22 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,321 reviews)
Everything that my wife and I experienced at this hotel was excellent. The staff , location , food ,drinks made our stay memorable. We highly recommend and will definitely be back.!!
Reviewed on 5 Sept 2026
Top hotels in Highland
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
€171
20 Sept - 21 Sept
includes taxes & fees
7/10 Good! (1,009 reviews)
"Clean rooms with double door security."
Reviewed on 4 Sept 2026
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
€91
20 Sept - 21 Sept
includes taxes & fees
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Fully refundableReserve now, pay when you stay
€126
7 Sept - 8 Sept
includes taxes & fees
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
€129
per adult
82% of travellers recommend
Frequently asked questions
How much does a Highland holiday package cost?
Offering great value package deals from €708 on Expedia, you'll be surprised at how little a holiday to Highland costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Highland?
You can generally find lower rates and better availability in January, February and November. Explore our cheap Highland holiday packages and you could get some great off-season discounts.
How many days is enough for Highland?
With a well-planned schedule, you can easily hit the most popular Highland attractions in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Highland holiday for longer.
How to find the best Highland package deals?
Use Expedia's handy filters to help you find some unbeatable Highland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Highland package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Highland holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and hotels individually. Better still, you can tailor your Highland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Highland?
If you're considering a spontaneous Highland trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?
- Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Highland.
- Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will probably be the biggest expense during your trip to Highland.
- Set the duration of your trip: Start by listing all the attractions you'd like to get to in Highland. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalised Highland holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
