Orland Park Vacations from $738

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,179, price is now $738 per person
$738
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,258 reviews)
I loved everything about this hotel. Great staff, great location and amazing rooftop.

Reviewed on Jun 1, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,325, price is now $821 per person
$821
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
The gym is on 43 floor.. amazing

Reviewed on May 31, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,422, price is now $926 per person
$926
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,753, price is now $1,163 per person
$1,163
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Extraordinarily lovely and helpful staff. This hotel manages to promote a staff and facility that beautifully balance solid upscale services with a true sence of welcome and connection, with a warm but unintrusive vibe and clear consideration of it's guests.

Reviewed on May 31, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,369, price is now $921 per person
$921
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Staff was amazing and the apartment building was phenomenally clean!

Reviewed on May 28, 2026

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Discover the most popular places to visit in Orland Park

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(336 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

What to do in Orland Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

$22
per child
98% of travellers recommend
Flyover in Chicago
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
$140 nightly
The price is $167 total per night from Jun 29 to Jun 30
$167 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,141 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."

Reviewed on May 31, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $242 total per night from Jun 30 to Jul 1
$242 total
Jun 30 - Jul 1
Total with taxes and fees
9.4/10 Exceptional! (4,309 reviews)
"I loved everything about this hotel. Great staff, great location and amazing rooftop."

Reviewed on Jun 1, 2026

Hotel Riu Plaza Chicago
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $160 total per night from Jun 29 to Jun 30
$160 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (3,043 reviews)
"Great price, the bunk beds were fun!"

Reviewed on Jun 1, 2026

Freehand Chicago
See all 3,406 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.

Find the Best Orland Park Vacation Packages

Orland Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
58,600
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Odyssey Fun World, Hollywood Casino Amphitheatre and Centennial Park

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Frequently asked questions

How much does an Orland Park vacation package cost?
Offering excellent value package deals from $738 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.