
Diamond Vacations from ¥267,343
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The Latest Diamond Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥374,596, price is now ¥267,343 per person
¥267,343
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on Jan 11, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥517,344, price is now ¥361,336 per person
¥361,336
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥382,283, price is now ¥286,916 per person
¥286,916
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026


The Peninsula Chicago
Downtown Chicago
Price was ¥536,808, price is now ¥407,372 per person
¥407,372
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 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 ¥12,750 per night from Feb 13 to Feb 14
¥12,750
¥14,787 total
Feb 13 - Feb 14
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
Clean rooms and hotel and friendly staff.
Reviewed on Jan 7, 2026

La Quinta Inn & Suites by Wyndham Shorewood
19715 NE Frontage Rd Joliet IL
Fully refundableReserve now, pay when you stay
The price is ¥15,330 per night from Jan 28 to Jan 29
¥15,330
¥17,780 total
Jan 28 - Jan 29
includes taxes & fees
9/10 Wonderful! (895 reviews)
Room was clean. Just an overnight stay.
Reviewed on Jan 2, 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.
