Northwest Side All inclusive Vacations
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Top All inclusive vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥453,524, price is now ￥272,138 per person
￥272,138
per person
May 1 - May 6
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everyone are helpful breakfast is amazing
Reviewed on Feb 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥494,822, price is now ￥365,182 per person
￥365,182
per person
May 1 - May 6
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥393,963, price is now ￥294,424 per person
￥294,424
per person
May 1 - May 6
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥400,475, price is now ￥304,811 per person
￥304,811
per person
May 1 - May 6
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
The location and views were the best!
Reviewed on Feb 18, 2026
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View all trips5* All inclusive vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥494,822, price is now ￥365,182 per person
￥365,182
per person
May 1 - May 6
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥587,878, price is now ￥471,300 per person
￥471,300
per person
May 1 - May 6
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The room was comfortable and beautiful design. Comfortable bed and bedding. Large desk. Good walkable location. But we could hear sirens at night
Reviewed on Feb 16, 2026
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View all trips3 Night All inclusive vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥373,341, price is now ￥278,734 per person
￥278,734
per person
May 13 - May 16
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everyone are helpful breakfast is amazing
Reviewed on Feb 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥346,104, price is now ￥295,819 per person
￥295,819
per person
May 13 - May 16
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026
Arlo Chicago
Downtown Chicago
Price was ￥348,052, price is now ￥299,496 per person
￥299,496
per person
May 13 - May 16
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Excellent customer service from Security to Front Desk ,Restaurant,cleanliness ,best amenities
Reviewed on Feb 16, 2026
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View all trips4 Night All inclusive vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥320,896, price is now ￥263,220 per person
￥263,220
per person
May 15 - May 18
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Room neat, clean and cozy. Check in was easy. Small and intimate for quick weekend getaway.
Reviewed on Feb 16, 2026
Arlo Chicago
Downtown Chicago
Price was ￥363,925, price is now ￥295,364 per person
￥295,364
per person
May 15 - May 18
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Excellent customer service from Security to Front Desk ,Restaurant,cleanliness ,best amenities
Reviewed on Feb 16, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥322,658, price is now ￥265,831 per person
￥265,831
per person
May 15 - May 18
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026
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See all available trips from Tokyo to Northwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
