
Riverside Vacations from ¥370,900
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The Latest Riverside Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago
Downtown Chicago
Price was ¥451,386, price is now ¥370,900 per person
¥370,900
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
2 blocks off Michigan ave, 1 block to the river, and great views of Lake Michigan. Staff was very helpful and kind.
Reviewed on May 15, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥488,788, price is now ¥389,378 per person
¥389,378
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
“Our stay was exceptional in every way. The hotel exceeded our expectations with its comfort, service, and overall atmosphere.”
Reviewed on May 15, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥583,097, price is now ¥471,416 per person
¥471,416
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!
Reviewed on May 13, 2026


Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ¥545,226, price is now ¥452,497 per person
¥452,497
per person
Aug 4 - Aug 9
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 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
Find the Best Riverside Vacation Packages
Riverside Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥21,202 per night from May 26 to May 27
¥21,202
¥25,207 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,129 reviews)
.
Reviewed on May 15, 2026

River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥22,803 per night from May 25 to May 26
¥22,803
¥27,110 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,181 reviews)
Clean room, great position, but small room and bed not queen as reserved, old amenities. No fridge.
Reviewed on May 15, 2026

Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥23,651 per night from May 25 to May 26
¥23,651
¥32,640 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,155 reviews)
Roof top bar
Reviewed on May 15, 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.
Discover the most popular places to visit in Riverside

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Riverside

Skydeck - Willis Tower Admission
¥7,012
per adult
96% of travellers recommend
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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.


