Orland Park Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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.
Level Chicago – Old Town
Downtown Chicago
CA $811
per person
Oct 28 - Oct 30
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay.
Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that.
Overall a great spot. Affordable and lots of space with great views!
Reviewed on Aug 15, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,501
per person
Oct 19 - Oct 23
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $905
per person
Oct 28 - Oct 30
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.
Reviewed on Aug 17, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
CA $1,843
per person
Oct 11 - Oct 15
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,384 reviews)
Broken elevator causing long lines and delays. Coffee set up in the lobby was awkward and $4 for a cup. Friends found bed bug in their bed. Staff very nice and good location.
Reviewed on Aug 16, 2026
Swissotel - Chicago
Downtown Chicago
CA $881
per person
Sep 27 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
Ready to book your vacation to Orland Park?
Orland Park Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Sep 8 - Sep 9
includes taxes & fees
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
CA $258
CA $348 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,272 reviews)
"Excellent stay"
Reviewed on Aug 16, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (857 reviews)
"Muy práctico todo solo que si es necesario que le digan a uno que tienen el inventario del apartamento para que no vayan a cobrar por algo que falte dentro del hotel. No todos los implementos estaban completos"
Reviewed on Aug 15, 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 great live music and acclaimed theater scene.
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
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
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 $811 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.
