Highland Trips (flight + hotel)

Photo by Joe Farmer

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Top hotels in Highland

Hilton Chicago/Oak Lawn
Hilton Chicago/Oak Lawn
3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is P7,727 per night from Jul 1 to Jul 2
P7,727
P8,884 total
Jul 1 - Jul 2
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"I like the location"

Reviewed on Jun 17, 2025

Hilton Chicago/Oak Lawn
Motel 6 - Chicago, IL
Motel 6 - Chicago, IL
2 out of 5
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P4,572 per night from Jun 29 to Jun 30
P4,572
P5,366 total
Jun 29 - Jun 30
includes taxes & fees
5.4/10 (19 reviews)
"I loved the fact that the room was modern and really clean, had a mini fridge, microwave and cable that actually worked and had a clear picture. What I didn’t like was I seen a roach in the bathroom. They may need to exterminate sooner than later."

Reviewed on Jun 16, 2025

Motel 6 - Chicago, IL
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
3.5 out of 5
18501 Convention Center Drive, Tinley Park, IL
Fully refundable
The price is P4,554 per night from Jun 29 to Jun 30
P4,554
P5,519 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
"Quick check in process, awesome check in people. Slower elevators, but one was being serviced and there was a sign to use the staff service elevators. Rooms were clean and amazing."

Reviewed on Jun 23, 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
See all 780 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.

Frequently asked questions

How much does a Highland vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Highland costs! Expedia's packages simplify travel planning and maximize 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 vacation 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 vacation 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 vacation package as early as possible.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation 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 vacation 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?

  1. 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.
  2. 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.
  3. 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.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Highland vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.