Orland Park Vacations from $295

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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!

The Latest Orland Park vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
Save 100% on your flight
Price was $475, price is now $295 per person
$295
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
In a great neighborhood. Quiet, clean. Excellent room layout. Free laundry was very nice to have. Nice breakfast.

Reviewed on Aug 14, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $900, price is now $561 per person
$561
per person
Nov 7 - Nov 12
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (431 reviews)
This is my go to place in the south suburbs.

Reviewed on Jul 30, 2025

Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Save 100% on your flight
Price was $465, price is now $298 per person
$298
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
8/10 Very Good! (1,008 reviews)
The room i stayed in had 4 different blue lights from the TV, M/C, red lighta from phone and clock and a flashing blue motion detector type light which madw it hard to fall asleep.

Reviewed on Aug 18, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,447, price is now $1,583 per person
$1,583
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
Food options need more variety.

Reviewed on Aug 16, 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $924, price is now $603 per person
$603
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,727 reviews)
Close to anything you wish to do in Chicago The free breakfast is way above what you would normally get and the evening happy hour was amazing. Bartender was awesome

Reviewed on Aug 17, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Orland Park

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Orland Park

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Orland Park

Orland Park Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$161 nightly
The price is $189 total per night from Sep 2 to Sep 3
$189 total
Sep 2 - Sep 3
Total includes taxes and fees
7.8/10 Good! (8,965 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on Aug 17, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
$161 nightly
The price is $189 total per night from Sep 3 to Sep 4
$189 total
Sep 3 - Sep 4
Total includes taxes and fees
8.4/10 Very Good! (4,717 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"

Reviewed on Aug 17, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $229 total per night from Sep 2 to Sep 3
$229 total
Sep 2 - Sep 3
Total includes taxes and fees
8.4/10 Very Good! (1,857 reviews)
"Loved the Palmer House Hotel!!! The lobby, amazing decoration! I even took a picture of it to post on social. The bar and restaurant area, very popular and looked like everyone was enjoying themselves! The room, well, not the best, but this was an occasion where I booked last minute and through a ..."

Reviewed on Aug 15, 2025

Palmer House a Hilton Hotel
See all 3,404 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.

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Frequently asked questions

How much does an Orland Park vacation package cost?
Offering excellent value package deals from $295 on Expedia, you'll be surprised at how little a vacation to Orland Park costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Orland Park?
January, March and April are the best times to search for cheap Orland Park vacation packages. Traveling in quieter periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Orland Park?
Orland Park vacations can be as short or long as you like, but to really sink your teeth into this destination, we'd suggest 2 days is a good ballpark. With this timeframe, you can fit in headline attractions like Orland Square and Orland Park Sportsplex and track down some lesser-known spots. Don't forget to visit neighborhoods such as Orland Hills and Southmoor either. If you plan wisely, you can even take a day trip or two from Orland Park too.
Is it worth booking a vacation package to Orland Park?
Well known for its golfing and home to popular attractions like Centennial Park, an Orland Park vacation is sure to leave an impression. Another highlight to check out? Don't miss Orland Square.
How to find the best Orland Park package deals?
Start your search for an Orland Park package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Orland Park package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Orland Park getaway off to a flying start.
Is it cheaper to book an Orland Park vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Orland Park vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Orland Park?
If you're planning a spontaneous Orland Park trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Orland Park vacation packages?
Set off on your dream escape to Orland Park with our Book Now, Pay Later vacations. No need to save up or wait for your next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.