South Side All inclusive Vacations
Book a All inclusive Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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 All inclusive vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥371,021, price is now ￥322,754 per person
￥322,754
per person
Dec 24 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
Great Location
Reviewed on Nov 9, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥440,564, price is now ￥343,515 per person
￥343,515
per person
Dec 24 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Great location to Miracle Mile, restaurants and grocery store!
Reviewed on Nov 8, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥405,868, price is now ￥332,054 per person
￥332,054
per person
Dec 24 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)
Good but the condition of the room wasn’t the best.
Reviewed on Nov 8, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥396,881, price is now ￥331,043 per person
￥331,043
per person
Dec 24 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Not worth it for the money. Good location but nothing special.
Reviewed on Nov 8, 2026
3 Night All inclusive vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Things to do
Skydeck Chicago at Willis Tower
￥6,636
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
