Great River Road Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Adventure vacation packages in Great River Road
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was ￥485,957, price is now ￥351,255 per person
￥351,255
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.
Reviewed on Mar 14, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥674,184, price is now ￥446,488 per person
￥446,488
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!
Reviewed on Mar 19, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥681,802, price is now ￥498,622 per person
￥498,622
per person
May 28 - Jun 2
found 23 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Family-friendly hotel in a great location—you can easily walk to the pier and enjoy all the nearby activities. Overnight valet parking is $75 per day, with unlimited in-and-out access, which is very convenient. The highlight of our stay was the excellent communication. You can simply text the staff for anything you need—extra towels, room cleaning, or forgotten items. No waiting on the phone or at the front desk, which made everything quick and hassle-free.
Reviewed on Mar 18, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥633,654, price is now ￥477,836 per person
￥477,836
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥681,242, price is now ￥515,418 per person
￥515,418
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips5* Adventure vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Minneapolis
Downtown Minneapolis
Price was ￥322,474, price is now ￥317,888 per person
￥317,888
per person
May 2 - May 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Minneapolis (MSP)
9.6/10 Exceptional! (308 reviews)
Loved our girls weekend at the Four Seasons. Spa was the best ever!
Reviewed on Mar 17, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥681,242, price is now ￥515,418 per person
￥515,418
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥669,111, price is now ￥644,030 per person
￥644,030
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful! Enjoyed a relaxing weekend.
Reviewed on Mar 18, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips3 Night Adventure vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥469,844, price is now ￥385,465 per person
￥385,465
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!
Reviewed on Mar 19, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥464,729, price is now ￥406,739 per person
￥406,739
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!
Reviewed on Mar 17, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥439,657, price is now ￥385,467 per person
￥385,467
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The hotel was nice , and clean. The guy at the front desk was super nice. However , the rooms are small, the shower water splashes over on to floor so extra towels are needed for the bathroom floor, and every vending machine was either jammed and or out of water.
Reviewed on Mar 17, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips4 Night Adventure vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥477,240, price is now ￥356,812 per person
￥356,812
per person
May 1 - May 5
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!
Reviewed on Mar 19, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
