Orland Park Vacations from $351

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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.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
The property does have a nice modern aesthetic and is pleasant looking. The bathroom door is a sliding door and it was difficult to open as well as it has a very chincy lock that you can tell is damaged. The photos of the outdoor patio space definitely made it appear nicer than it actually is but was still at least pleasant. Check in staff seemed a little offputting and slightly pushy to get me going when I was asking questions. Breakfast is not complimentary and is quite expensive but there are nearby options to eat still. Overall seemed a little bit overpriced for the stay.

Reviewed on Aug 11, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on Aug 11, 2025

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (4,622 reviews)
price for parking is to high

Reviewed on Aug 12, 2025

Staybridge Suites Chicago - Glenview by IHG

Staybridge Suites Chicago - Glenview by IHG

3 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The room was very clean! I loved having an ice maker too! The staff was very helpful too. Highly recommend this hotel!

Reviewed on Aug 8, 2025

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
My favorite part of my stay was the shower . I love the led lights in the shower . It’s so cool at night to watch the shower change colors .

Reviewed on Aug 11, 2025

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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

4.5/5(2,128 reviews)

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

4.5/5(332 reviews)

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

4.5/5(4,870 reviews)

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
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,943 reviews)
"The hotel room was quiet and clean, only a little old and something outdated but still functional (tv). The area is great to visit a lot of the Chicago attractions and staff was helpful. Would recommend!"

Reviewed on Aug 11, 2025

Congress Plaza Hotel
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 4 to Sep 5
$229 total
Sep 4 - Sep 5
Total includes taxes and fees
8.4/10 Very Good! (1,848 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on Aug 11, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $185 total per night from Aug 26 to Aug 27
$185 total
Aug 26 - Aug 27
Total includes taxes and fees
8.4/10 Very Good! (3,662 reviews)
"The staff was kind and helpful. The rooms and hotel itself were pretty clean. It's in a heavily populated area of a major US city - you're going to hear noises from outside at night, so just know that going into it(I've seen people complaining about it in reviews). I never felt unsafe walking around ..."

Reviewed on Aug 11, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 3,407 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 $351 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.