Monticello Vacations from ￥349,994
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The Latest Monticello Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥659,915, price is now ￥426,058 per person
￥426,058
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Staff was very courteous and helpful
Reviewed on Mar 13, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥560,889, price is now ￥424,265 per person
￥424,265
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on Mar 13, 2026
Hilton Chicago
Downtown Chicago
Price was ￥605,910, price is now ￥499,852 per person
￥499,852
per person
May 28 - Jun 1
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on Mar 12, 2026
Find the Best Monticello Vacation Packages
Monticello Hotel Deals
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello WI
10/10 Exceptional! (157 reviews)
The host was super great an massaged me early with all the information I needed. They even offered dining recommendations. The house slept 10 and we had ample towels and toilet paper. The house is super cute! The only downside, the driveway is a little steep up to the house, so we were glad it didn't ...
Reviewed on Jan 27, 2026
Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is ￥11,602 per night from Mar 22 to Mar 23
￥11,602
￥13,400 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
Would definitely stay here again.
Reviewed on Mar 12, 2026
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is ￥10,282 per night from Mar 22 to Mar 23
￥10,282
￥11,877 total
Mar 22 - Mar 23
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
Love it
Reviewed on Mar 11, 2026
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.
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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.
