
Steward Vacations from ¥223,048
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The Latest Steward Vacation Packages
Price found within the past 48 hours. Click for updated prices.

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 16 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

Level Chicago - River North
Downtown Chicago
Price was ¥280,959, price is now ¥226,887 per person
¥226,887
per person
Dec 3 - Dec 8
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay
Reviewed on Sep 19, 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 16 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

Arlo Chicago
Downtown Chicago
Price was ¥281,081, price is now ¥232,163 per person
¥232,163
per person
Dec 3 - Dec 8
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
We loved the atmosphere, style and the location. The beds are super comfortable, the room large and the bathroom was really great. The only issue we had was with food quality in the dining room and though our room service breakfast was tasty, it was served as take out- no coffee pot or plates. Hopefully they will change this as they get more established.
Reviewed on Sep 24, 2025
Find the Best Steward Vacation Packages
Steward Hotel Deals

Hampton Inn DeKalb, IL
663 S. Annie Glidden Road, DeKalb, IL
Fully refundableReserve now, pay when you stay
The price is ¥18,283 per night from Oct 15 to Oct 16
¥18,283
¥20,748 total
Oct 15 - Oct 16
includes taxes & fees
9.2/10 Wonderful! (971 reviews)
Business As Usual
"All Good, Stay here at least once a month. No problems here"
Reviewed on Sep 24, 2025

Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road, Sycamore, IL
Fully refundable
The price is ¥12,787 per night from Sep 29 to Sep 30
¥12,787
¥14,191 total
Sep 29 - Sep 30
includes taxes & fees
8.4/10 Very Good! (893 reviews)
"Nice staff. Great breakfast and excellent Food Service Worker. Carpet in the room definitely needed cleaning. It was kinda sticky and gross. Sink handle was loose but worked ok."
Reviewed on Sep 22, 2025

Best Western Sycamore Inn
1935 Dekalb Ave, Sycamore, IL
Fully refundableReserve now, pay when you stay
The price is ¥13,891 per night from Oct 6 to Oct 7
¥13,891
¥15,416 total
Oct 6 - Oct 7
includes taxes & fees
8/10 Very Good! (354 reviews)
"Friendly staff, excellent housekeeping team ."
Reviewed on Aug 20, 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.
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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.