Orland Park Vacations

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Find the Best Orland Park Vacation Packages

Orland Park Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 426 per night from Nov 22 to Nov 23
AEDĀ 426
AEDĀ 507 total
22 Nov - 23 Nov
includes taxes & fees
8/10 Very Good! (10,180 reviews)
"This is an older hotel with a lot of rooms, so I am never sure what to expect -- but this was a good stay. We stored our bags at the beginning and end of our stay with no problems. Our room was in the north tower and it had been refurbished. Beds were comfortable enough, and it was clean even if ..."

Reviewed on 12 November 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 389 per night from Dec 10 to Dec 11
AEDĀ 389
AEDĀ 463 total
10 Dec - 11 Dec
includes taxes & fees
8.8/10 Excellent! (5,597 reviews)
"."

Reviewed on 12 November 2026

River Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 496 per night from Nov 26 to Nov 27
AEDĀ 496
AEDĀ 699 total
26 Nov - 27 Nov
includes taxes & fees
8.6/10 Excellent! (3,538 reviews)
"Everything good"

Reviewed on 11 November 2026

Hilton Chicago
See all 3,269 properties in Orland Park
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)
Orland Square Mall offers over 130 stores and dining options in Chicago's southwest suburbs. Browse upscale retailers like Apple and Sephora, then indulge at The Cheesecake Factory or Texas de Brazil.
See properties

Frequently asked questions

How much does a Orland Park vacation package cost?
Offering excellent value package deals 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. Traveling in quieter months means you can generally find lower prices on accommodations and flights.
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?

  1. Choose your dates: What you'd like to do in Orland Park and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.