Orland Park Vacation Packages
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Your Orland Park Vacation
Get ready to experience Orland Park on your terms with a custom Orland Park vacation package! Discovering the treasures of this lively city is easy with a base in a neighborhood such as Flossmoor, which is great for golfing, among lots of other things. Like to get out and explore? Orland Park Sportsplex, Orland Square and Centennial Park are just a few of the most popular places to visit during a trip to Orland Park. Stop dreaming and start doing. Browse the broad range of options on Expedia today and finally put your Orland Park vacation plans into gear!
Top Orland Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
Ready to book your vacation to Orland Park?
Orland Park Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $238
CA $283 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (5,460 reviews)
"Location location Close to everything"
Reviewed on Oct 1, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $182
CA $216 total
Nov 1 - Nov 2
includes taxes & fees
Hilton Chicago
720 S Michigan Ave Chicago IL
CA $236
CA $322 total
Oct 30 - Oct 31
includes taxes & fees
8.6/10 Excellent! (3,329 reviews)
"Having a Starbucks on property was very helpful! Good location and incredibly helpful staff."
Reviewed on Oct 1, 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.
Stay near popular Orland Park attractions
Orland Square
8.4/10 (33 reviews)
You can do some window-shopping at Orland Square during your stay in Orland Park. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Centennial Park
7.8/10 (17 reviews)
Explore the great outdoors at Centennial Park, a lovely green space in Orland Park. Experience the great live music or attend a sporting event in this family-friendly area.
Orland Park Sportsplex
8.0/10 (25 reviews)
Take the family on an outing to Orland Park Sportsplex during your trip to Orland Park. Experience the area's acclaimed theater scene and great live music.
Centennial Park Aquatic Center
7.6/10 (8 reviews)
Enjoy the thrill rides with your kiddos at Centennial Park Aquatic Center as part of your trip to Orland Park. Experience the great live music or attend a sporting event in this family-friendly area.
Space Golf
6.8/10 (11 reviews)
Enjoy a round of golf in Orland Park at Space Golf. Experience the great live music or attend a sporting event in this family-friendly area.
What to do in Orland Park
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Orland Park vacation package cost?
Offering excellent value package deals from CA $983 on Expedia, you'll be thrilled with how little a vacation to Orland Park costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Orland Park?
March, September and October are the best times to search for cheap Orland Park vacation packages. Travelling in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Orland Park?
With around 2 days, you'll have plenty of time to visit popular neighbourhoods such as Orland Hills and Southmoor during your Orland Park vacation. Remember to also add Orland Park Sportsplex and George Dunne National Golf Club to your list of must-sees. In the mood for more adventures? Consider venturing outside of Orland Park on tours and day trips.
Is it worth booking a vacation package to Orland Park?
Known for its golfing and home to popular attractions like Centennial Park, a Orland Park vacation is bound to impress. Another top sight to visit? Don't miss Orland Square.
How to find the best Orland Park package deals?
Use Expedia's handy filters to help you find some great Orland Park package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Orland Park package deals in the low season. Play around with your travel dates and you may score even bigger 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 Orland Park vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations separately. Better still, you can tailor your Orland Park trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Orland Park?
If you have your Orland Park vacation dates confirmed, book as soon as you can to bag some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Orland Park?
- Choose your dates: What you'd like to do in Orland Park and your preferred season can help you decide when to go.
- Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and flights. Your accommodations will probably be the largest expense during your trip to Orland Park.
- Decide how long to go away for: Now that you know more about Orland Park, you can figure out the right length of your vacation. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Orland Park vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
