
Far Southwest Side All inclusive Vacations
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Top All inclusive vacation packages in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥263,537, price is now ¥223,048 per person
¥223,048
per person
Nov 28 - Nov 30
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast buffet was excellent. Shortage of cleaning staff created some problems—two times the room wasn’t serviced until after 5:00 p.m. Room was fine but we needed information about turning on and using the TV. Also needed instructions on using the soap dispensers in the bathroom. Seems trivial, but it’s the little things that separate good from excellent. Staff was cordial and helpful.
Reviewed on Sep 27, 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 19 hours 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

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥320,939, price is now ¥259,332 per person
¥259,332
per person
Nov 28 - Nov 30
found 23 hours 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

Arlo Chicago
Downtown Chicago
Price was ¥281,081, price is now ¥232,163 per person
¥232,163
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
Great room. Very nice staff. We loved it. The scent in the lobby was nice but a little strong. I would stay here again.
Reviewed on Sep 27, 2025

The Royal Sonesta Chicago River North
Downtown Chicago
Price was ¥401,106, price is now ¥341,098 per person
¥341,098
per person
Nov 1 - Nov 7
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
The hotel offers nothing other than a room and a fitness center which we did not use. There is no food or drink available at the hotel. Women at the front desk were very friendly and helpful.
Reviewed on Sep 26, 2025
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View all trips5* All inclusive vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥320,939, price is now ¥259,332 per person
¥259,332
per person
Nov 28 - Nov 30
found 23 hours 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


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 23 hours 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
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View all trips3 Night All inclusive vacations in Far Southwest 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 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast buffet was excellent. Shortage of cleaning staff created some problems—two times the room wasn’t serviced until after 5:00 p.m. Room was fine but we needed information about turning on and using the TV. Also needed instructions on using the soap dispensers in the bathroom. Seems trivial, but it’s the little things that separate good from excellent. Staff was cordial and helpful.
Reviewed on Sep 27, 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 10 hours 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 10 hours 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
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