Highland Holidays
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Highland Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa
S$581
per person
2 Oct - 4 Oct
found 12 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (1,249 reviews)
Stayed here for the nostalgia. My dad worked for Nordic Hills when I was a kid and I spent a lot of time there in the 70’s and 80’s. It has been significantly changed but not for the better. The cool octagonal indoor pool is gone, the outdoor pool is gone. There is a new indoor pool, which is decent. The lady who runs the little bowling alley is very nice. They really need to fix the bowling alley if they’re going to charge guests to use it. $30 per hour is a little expensive for electronics that doesn’t count the pins correctly. There aren’t enough sizes to use bowling shoes and the balls and lanes are very worn. Overall we had a fun time though. They should just include it in the price if they’re room honestly. The downstairs restaurant used to be awesome. Now it’s meh. Very limited menu of seemingly microwaved food. Bring back The Viking Room and the two-sided fireplace! We were charged $10 per car to park in the parking lot. Not sure why…Glad we went but they should have kept the stuff that made the place cool and unique back in the day. People seem to like the golf course.
Reviewed on 23 Aug, 2026
Top hotels in Highland
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
S$222
25 Aug - 26 Aug
includes taxes & fees
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
S$114
7 Sept - 8 Sept
includes taxes & fees
Quality Inn & Suites Orland Park - Chicago
8800 W 159th St Orland Park IL
Fully refundable
S$130
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
S$192
per adult
82% of travellers recommend
Frequently asked questions
How much does a Highland holiday package cost?
Offering great value package deals from S$581 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. 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.
