Orland Park Vacations from ￥200,594
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Orland Park Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥256,630, price is now ￥200,594 per person
￥200,594
per person
Mar 15 - Mar 20
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Great view, awesome bar, fun staff.
Reviewed on Dec 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥385,898, price is now ￥274,520 per person
￥274,520
per person
Mar 15 - Mar 20
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent! Everything was perfect, beautiful and the staff are amazing!
Reviewed on Dec 27, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥399,685, price is now ￥297,235 per person
￥297,235
per person
Mar 15 - Mar 20
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
They went above and beyond! Perfect stay!
Reviewed on Dec 26, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥271,780, price is now ￥207,398 per person
￥207,398
per person
Feb 11 - Feb 17
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Early check in available for $25, worth it for getting rest between flights. Very friendly staff
Reviewed on Dec 27, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥285,935, price is now ￥221,613 per person
￥221,613
per person
Mar 15 - Mar 20
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Find the Best Orland Park Vacation Packages
Orland Park Hotel Deals
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥20,542 per night from Jan 2 to Jan 3
￥20,542
￥28,030 total
Jan 2 - Jan 3, 2026
includes taxes & fees
8.4/10 Very Good! (2,170 reviews)
Clean rooms, extremely friendly staff, onsite Starbucks, Lockwood restaurant was amazing, beautiful gathering area in the lounge. Close to all the Christmas must do’s. Decorated so so beautifully for Christmas!
Reviewed on Dec 24, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,152 reviews)
Very friendly and helpful staff
Reviewed on Dec 23, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,776 per night from Jan 9 to Jan 10
￥12,776
￥14,998 total
Jan 9 - Jan 10, 2026
includes taxes & fees
8.6/10 Excellent! (2,014 reviews)
Easy check in. Ready to upgrade. I love how central it is and the water stations on each floor. This is our second time to stay here and will do it again!
Reviewed on Dec 23, 2025
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
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.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Orland Park
Wendella's 90-min Chicago River Architecture Tour
￥6,310
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,827
per adult
88% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
