South 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 South Side
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥261,601, price is now ￥208,560 per person
￥208,560
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
Great place to stay, close to everything!
Reviewed on Sep 28, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥285,100, price is now ￥220,732 per person
￥220,732
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay. Clean and quiet and conveniently located to all types of eating, shopping, and river walk.
Great breakfast buffet to start the day and fantastic rooftop bar for the evening!
Reviewed on Sep 28, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥321,620, price is now ￥259,612 per person
￥259,612
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
The property was clean and the bed very comfortable. Stayed here on a travel layover -- it was super convenient to the airport. They also have a restaurant that was open late -- very helpful, and the food was pretty good.
Reviewed on Sep 28, 2025
Level Chicago - River North
Downtown Chicago
Price was ￥280,959, price is now ￥226,887 per person
￥226,887
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay
Reviewed on Sep 19, 2025
5* All inclusive vacations in South Side
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥279,276, price is now ￥272,536 per person
￥272,536
per person
Nov 28 - Nov 30
found 2 days ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one.
Reviewed on Sep 15, 2025
3 Night All inclusive vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥366,658, price is now ￥298,221 per person
￥298,221
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay. Clean and quiet and conveniently located to all types of eating, shopping, and river walk.
Great breakfast buffet to start the day and fantastic rooftop bar for the evening!
Reviewed on Sep 28, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥410,157, price is now ￥331,901 per person
￥331,901
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe
Reviewed on Sep 27, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥357,383, price is now ￥302,136 per person
￥302,136
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025
4 Night All inclusive vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥321,722, price is now ￥261,166 per person
￥261,166
per person
Nov 2 - Nov 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay. Clean and quiet and conveniently located to all types of eating, shopping, and river walk.
Great breakfast buffet to start the day and fantastic rooftop bar for the evening!
Reviewed on Sep 28, 2025
The Emily Hotel
Downtown Chicago
Price was ￥356,734, price is now ￥288,542 per person
￥288,542
per person
Nov 2 - Nov 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September.
Rooms were clean modern and had loads of desk space but no dressers or nightstands.
Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily.
We would stay there again.
Reviewed on Sep 26, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
