Orland Park Vacations from $490

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $828, price is now $490 per person
$490
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.

Reviewed on May 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $991, price is now $577 per person
$577
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,127 reviews)
The hotel was clean, staff was friendly and very helpful. My room was clean and the breakfast buffet was phenomenal. I recommend this hotel and will be a returning customer.

Reviewed on May 18, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $787, price is now $496 per person
$496
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Lovely stay and we are at Toro right in the hotel. Fabulous dinner

Reviewed on May 18, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $854 per person
$854
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
The Sable was beautiful and peaceful. We enjoyed our stay and would definitely come back. Thanks for the great customer service.

Reviewed on May 17, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,025, price is now $653 per person
$653
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities

Reviewed on May 3, 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
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

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

Navy Pier

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
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,150 reviews)
"Always stay here when I’m trying to save money great location and price"

Reviewed on May 17, 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
$184 nightly
The price is $219 total per night from May 26 to May 27
$219 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (4,176 reviews)
"The hotel was clean, staff was friendly and very helpful. My room was clean and the breakfast buffet was phenomenal. I recommend this hotel and will be a returning customer."

Reviewed on May 18, 2026

Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $142 total per night from May 26 to May 27
$142 total
May 26 - May 27
Total with taxes and fees
8.2/10 Very Good! (2,707 reviews)
"Our room was directly next to the elevators and it was very noisy all night long. The AC would not go below a certain temperature and it was very warm in the room all night no matter how low the temperature was placed. The room was very small and did not provide a lot of comfort."

Reviewed on May 17, 2026

Hotel Felix River North/Magnificent Mile
See all 3,405 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 $490 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.