Diamond Vacations from ￥357,749
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The Latest Diamond Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Price was ￥716,628, price is now ￥518,857 per person
￥518,857
per person
May 29 - Jun 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
The check in process was a little crazy, can’t say I have ever needed a background check to stay somewhere so it was a bit time consuming although I suppose good to know safety is a priority. View from property was the best part hands down! Cost of overall stay was great deal, parking for $65 a night was a bit disappointing because it is nice to have it on site. Overall would stay again.
Reviewed on Apr 14, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥711,740, price is now ￥515,764 per person
￥515,764
per person
May 29 - Jun 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The staff was the best part of the hotel, accommodating, polite and patient. Rooms were so so but they offer so many amenities that is more than makes up for it
Reviewed on Apr 14, 2026
Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
Price was ￥543,638, price is now ￥431,376 per person
￥431,376
per person
May 29 - Jun 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,520 reviews)
This is our favorite hotel in Chicago. The only thing that was different on our last trip was the parking garage next door. It is under new ownership, and they made it very difficult to leave and come back, even though we bought a three-day pass with in-and-out privileges. The management at Claridge House is aware of the situation and is working on a solution.
Reviewed on Apr 12, 2026
Find the Best Diamond Vacation Packages
Diamond Hotel Deals
aruba- la cabana beach resort and casino
Diamond IL
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is ￥13,546 per night from Apr 22 to Apr 23
￥13,546
￥15,711 total
Apr 22 - Apr 23
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
They are updating all their rooms, so it's a little messy, but overall very clean and great staff. My room was perfect for me, the pool and hot tub were nice, and the breakfast hit the spot. I can't give them anything but an A- We will stay there on our next trip through town.
Reviewed on Apr 13, 2026
La Quinta Inn & Suites by Wyndham Shorewood
19715 NE Frontage Rd Joliet IL
Fully refundableReserve now, pay when you stay
The price is ￥17,239 per night from May 11 to May 12
￥17,239
￥19,994 total
May 11 - May 12
includes taxes & fees
9.2/10 Wonderful! (945 reviews)
Everything was exceptionally well!!
Reviewed on Apr 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.
