Orland Park Vacation Packages

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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!

Top Orland Park Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Chicago-Vernon Hills by IHG

Hotel Indigo Chicago-Vernon Hills by IHG

3.5 out of 5
per person
Jul. 5 - Jul. 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (923 reviews)
Better coffee service- they tried

Reviewed on Apr. 19, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 29 - Jul. 4
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
The remodel is fantastic!

Reviewed on Apr. 19, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 29 - Jul. 4
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
We had a wonderful stay at the Peninsula Hotel. Very luxurious overall, top-notch service, very comfortable bed, and great location in the heart of Chicago.

Reviewed on Apr. 16, 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Jul. 5 - Jul. 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (24 reviews)
The property itself is in a great location and offers good value for the price. However, the experience was unfortunately overshadowed by poor customer service. Upon booking, we received multiple links with different sets of information—one with property details, another with check-in instructions, and other links as well. Assuming there was a master link as the webpage seemed to suggest, we missed the one specifically for check-in. When we arrived just after 4pm on 04/17, we used the keypad to contact the property for assistance. The woman who answered the call was unnecessarily rude and dismissive—something that could have been avoided with a simple, helpful response. A little courtesy goes a long way, especially in hospitality. The stay itself was fine, but the unprofessional attitude of certain staff members left a lasting negative impression. With better communication and a more respectful approach to guests, this property could truly stand out.

Reviewed on Apr. 20, 2025

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Orland Park Hotel Deals

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
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Apr. 21 to Apr. 22
CA $220
CA $258 total
includes taxes & fees
Apr 21 - Apr 22
8.2/10 Very Good! (3,897 reviews)
"Very convenient place"

Reviewed on Apr. 18, 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $249 per night from May 11 to May 12
CA $249
CA $333 total
includes taxes & fees
May 11 - May 12
8.8/10 Excellent! (2,063 reviews)
"Room cleaning crew paid attention to every detail, even put a small towel under my toiletries."

Reviewed on Apr. 18, 2025

Swissotel - Chicago
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $174 per night from May 4 to May 5
CA $174
CA $205 total
includes taxes & fees
May 4 - May 5
8.8/10 Excellent! (1,020 reviews)
"Everything was ok except for parking."

Reviewed on Apr. 20, 2025

Crowne Plaza Chicago West Loop by IHG
See all 2,994 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Orland Park vacation package cost?
Offering excellent value package deals from CA $815 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?
March, September and October are the best times to look for cheap Orland Park vacation packages. Opting to travel in less busy months means you can usually find reduced prices on accommodations and flights.
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 say 2 days is a good ballpark. With this timeframe, you can visit headline attractions like Orland Square and Orland Park Sportsplex as well as underrated spots. Don’t forget to explore neighborhoods such as Orland Hills and Southmoor either. If you’re smart with your time, you can even take a day trip or two from Orland Park too.
Is it worth booking a vacation package to Orland Park?
Boasting a host of highlights starting with its excellent golfing, Orland Park is a good vacation destination. Whether you’d like to visit attractions like Centennial Park and Orland Square or take the path less traveled, you’ll have plenty to keep you busy during your Orland Park vacation.
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.
How to plan a trip to Orland Park?

  1. Pick your travel dates: The things you’d like to do in Orland Park and your preferred season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and flights. Your accommodations will likely be the largest expense during your trip to Orland Park.
  3. Work out your trip length: Think about how much time you’d like to spend discovering Orland Park. Plan your days so you can get to all the attractions and experiences you’re interested in without rushing.
  4. Combine your airfare and accommodations: After you’ve settled on your trip dates and duration, lock in the right Orland Park vacation package for you.

Discover the most popular places to visit in Orland Park

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

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

Michigan Avenue

4.5/5(19 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
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Orland Park

Flyover in Chicago

Flyover in Chicago

CA $55
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $70
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $64
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Orland Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.