
Waterman Vacations from ¥443,448
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The Latest Waterman Vacation Packages
Price found within the past 48 hours. Click for updated prices.

The Emily Hotel
Downtown Chicago
Price was ¥524,160, price is now ¥443,448 per person
¥443,448
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Very cute boutique hotel. Very clean. Staff were very helpful. I loved the two young ladies in coffee shop. They were so efficient, welcoming and warm.
Reviewed on May 18, 2026

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ¥550,415, price is now ¥455,778 per person
¥455,778
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on May 12, 2026

ENVITAE Hotel 4 Bedroom Luxury Apartments
Near North Side
Price was ¥688,552, price is now ¥580,174 per person
¥580,174
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (16 reviews)
⭐⭐⭐⭐⭐
We had a fantastic stay in this 4-bedroom apartment hotel. Looks exactly like the pictures. The unit was spotlessly clean and perfectly appointed — it truly felt like a home away from home. The kitchen had every amenity you could possibly need, which made cooking and relaxing with family incredibly easy.
The bedding was beautiful and very comfortable, and having a washer and dryer in the unit was a huge bonus, especially for a longer stay.
The building itself felt very secure, including the parking area, which gave us great peace of mind. We also loved the amenities — the gym and lounge area were excellent and well maintained.
Overall, this was one of the best apartment-style stays we’ve had. Comfortable, convenient, and thoughtfully set up. We would absolutely stay here again.
Reviewed on Mar 5, 2026


The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was ¥593,821, price is now ¥508,558 per person
¥508,558
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
No coffee machines in the room but free coffee in the lobby. Great location. The bar is a scene and the rooftop patio is a beautiful space. Great sound insulation and comfy beds.
Reviewed on May 13, 2026
Find the Best Waterman Vacation Packages
Waterman Hotel Deals

Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
Fully refundableReserve now, pay when you stay
The price is ¥20,817 per night from May 26 to May 27
¥20,817
¥23,623 total
May 26 - May 27
includes taxes & fees
9.2/10 Wonderful! (447 reviews)
"Breakfast was above average. Room clean, and well kept. Staff was friendly."
Reviewed on May 18, 2026

Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is ¥19,542 per night from Jun 3 to Jun 4
¥19,542
¥22,175 total
Jun 3 - Jun 4
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"Staff was friendly and helpful and the breakfast was great!"
Reviewed on May 16, 2026

Super 8 by Wyndham Rochelle
601 E Highway 38 Rochelle IL
Fully refundableReserve now, pay when you stay
The price is ¥10,794 per night from May 31 to Jun 1
¥10,794
¥11,979 total
May 31 - Jun 1
includes taxes & fees
8.2/10 Very Good! (994 reviews)
"We arrived late at night. The agent was pleasant, professional and efficient. The room was comfortable and clean."
Reviewed on May 12, 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.
