Orland Park Vacations from ￥232,596

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The Latest Orland Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Doorman was delightful! King room was spacious. Toilet flush was problematic. The pool was not open despite the advertisement on the Expedia websit. Lots of additional, non-negotiable charges once you get there.

Reviewed on Aug 11, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 17 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on Aug 11, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 17 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Great location with many great food and drink options. The room is a modern industrial design with unfinished walls and ceiling. It looks nice but not exactly my style. The room was clean and was comfortable for a two night stay.

Reviewed on Aug 12, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on Aug 11, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location was good. Staff was friendly. It was clean. But it was hard to enjoy time in the room because of the TV. They had horrible cable with nothing on, and it wasn’t a smart tv so we couldn’t log into any of our streaming services or even stream from our phones to the tv. We had to go out and buy a firestick.

Reviewed on Aug 10, 2025

Find the Best Orland Park Vacation Packages

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
The price is ￥19,897 per night from Sep 1 to Sep 2
￥19,897
￥23,356 total
Sep 1 - Sep 2
includes taxes & 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
The price is ￥25,618 per night from Aug 21 to Aug 22
￥25,618
￥33,767 total
Aug 21 - Aug 22
includes taxes & 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
The price is ￥22,671 per night from Aug 24 to Aug 25
￥22,671
￥26,612 total
Aug 24 - Aug 25
includes taxes & 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.

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

￥6,122
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,646
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

￥5,981
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Orland Park

Frequently asked questions

How much does an Orland Park vacation package cost?
Offering excellent value package deals from ￥232,596 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.

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