Great River Road Romantic Vacations
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Top Romantic vacation packages in Great River Road
Price found within the past 48 hours. Click for updated prices.
L7 Chicago by LOTTE
Downtown Chicago
Price was ￥564,562, price is now ￥482,919 per person
￥482,919
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (3,846 reviews)
The room is larger than you would expect for a downtown hotel and the staff is wonderfully friendly. They really make you feel special.
Reviewed on Apr 12, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥449,128, price is now ￥385,259 per person
￥385,259
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Helpful staff, great location, adequate rooms!
Reviewed on Apr 14, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥493,535, price is now ￥428,776 per person
￥428,776
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,132 reviews)
The lobby was nice. Friendly service. Parking was expensive 😭
Reviewed on Apr 12, 2026
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View all trips5* Romantic vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥384,943, price is now ￥336,512 per person
￥336,512
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥388,047, price is now ￥341,942 per person
￥341,942
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
A beautiful hotel with an outstanding staff in a superb location.
Reviewed on Apr 12, 2026
Park Hyatt Chicago
Downtown Chicago
Price was ￥389,916, price is now ￥344,349 per person
￥344,349
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
I truly enjoyed my 5 night stay at this hotel. Everyone was helpful, friendly, and accommodating. I love its location, near the Michael mile.
When I return to Chicago I will definitely stay at the Park Hyatt.
Reviewed on Apr 4, 2026
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View all trips3 Night Romantic vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
L7 Chicago by LOTTE
Downtown Chicago
Price was ￥564,562, price is now ￥482,919 per person
￥482,919
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (3,846 reviews)
The room is larger than you would expect for a downtown hotel and the staff is wonderfully friendly. They really make you feel special.
Reviewed on Apr 12, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥449,128, price is now ￥385,259 per person
￥385,259
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Helpful staff, great location, adequate rooms!
Reviewed on Apr 14, 2026
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See all available trips from Tokyo to Great River Road
View all trips4 Night Romantic vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥379,304, price is now ￥305,586 per person
￥305,586
per person
May 18 - May 22
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Great stay! Loved to come back. Friendly staff!
Reviewed on Apr 13, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥382,774, price is now ￥325,683 per person
￥325,683
per person
May 18 - May 22
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
I would highly recommend this hotel. The only issue we had was that there was not daily cleaning. I actually never saw hotel cleaning staff in the halls, but the room and hotel were very clean so I am not sure where they were. The hotel is near so many attractions and restaurants. On the second floor is a room with a pool table, air hockey, and other games which was a nice break.
Reviewed on Apr 13, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
