West Side All inclusive Vacations
Book a All inclusive Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top All inclusive vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥399,680, price is now ￥292,724 per person
￥292,724
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location
Reviewed on Aug 20, 2025
Park Hyatt Chicago
Downtown Chicago
Price was ￥574,886, price is now ￥399,750 per person
￥399,750
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug 10, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥589,400, price is now ￥417,931 per person
￥417,931
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥665,218, price is now ￥471,834 per person
￥471,834
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥463,004, price is now ￥335,482 per person
￥335,482
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Nice, clean and safe
Reviewed on Aug 20, 2025
5* All inclusive vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was ￥574,886, price is now ￥399,750 per person
￥399,750
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug 10, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥589,400, price is now ￥417,931 per person
￥417,931
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥665,218, price is now ￥471,834 per person
￥471,834
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.