
Caledonia Vacations from ¥221,544
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Caledonia Vacation Packages
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥253,084, price is now ¥221,544 per person
¥221,544
per person
Nov 28 - Nov 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥320,939, price is now ¥259,332 per person
¥259,332
per person
Nov 28 - Nov 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥263,537, price is now ¥223,048 per person
¥223,048
per person
Nov 28 - Nov 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
They had a buffet in the hotel which was great and it’s in a great location . Close to everything
Reviewed on Sep 26, 2025


DoubleTree by Hilton Chicago Schaumburg
Price was ¥264,584, price is now ¥232,014 per person
¥232,014
per person
Nov 14 - Nov 20
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
7.4/10 Good! (1,002 reviews)
The surrounding area is nice. The rooms need an upgrade and more cleaning. I wouldn’t stay here again. I arrived early and the front desk agent was not friendly.
Reviewed on Sep 22, 2025
Find the Best Caledonia Vacation Packages
Caledonia Hotel Deals

Baymont by Wyndham Rockford
662 N Lyford Rd, Rockford, IL
Fully refundableReserve now, pay when you stay
The price is ¥11,186 per night from Oct 2 to Oct 3
¥11,186
¥12,750 total
Oct 2 - Oct 3
includes taxes & fees
9/10 Wonderful! (1,336 reviews)
"Good location, economical, good breakfast, great staff"
Reviewed on Sep 24, 2025

Holiday Inn Rockford by IHG
7550 E State Street, Rockford, IL
Fully refundable
The price is ¥13,927 per night from Oct 12 to Oct 13
¥13,927
¥15,874 total
Oct 12 - Oct 13
includes taxes & fees
8.4/10 Very Good! (964 reviews)
"Overall, excellent I did have an issue with not being able to turn on the shower, but the staff accommodated me and it was a common problem for other guests. Everybody has trouble turning on the showers."
Reviewed on Sep 23, 2025

Econo Lodge
7712 Potawatomi Trail, Rockford, IL
Fully refundableReserve now, pay when you stay
The price is ¥8,783 per night from Oct 5 to Oct 6
¥8,783
¥10,011 total
Oct 5 - Oct 6
includes taxes & fees
8.2/10 Very Good! (983 reviews)
"Its was quite and nice for one night"
Reviewed on Sep 19, 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.
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.