
Far Southeast Side Luxury Vacations
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Top Luxury vacation packages in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥230,232, price is now ¥158,343 per person
¥158,343
per person
Nov 13 - Nov 17
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Overall, the stay was enjoyable. Nice facilities. We really enjoyed the Rooftop restaurant on our first night. Suggestions for improvement include offering a variety of pillow options (preferably down alternatives), a microwave in the room, and vending or self-serve options for water or snacks. My son had to go to a 7-Eleven for water and Gatorade (even though we are club members). The night staff informed me that only one bottle of water was complimentary. I would have gladly paid for one, but that apparently wasn't an option either.
Reviewed on Sep 3, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥328,496, price is now ¥222,669 per person
¥222,669
per person
Nov 13 - Nov 17
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep 2, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ¥403,008, price is now ¥280,014 per person
¥280,014
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
Friendly and helpful staff
Reviewed on Sep 3, 2025

The Emily Hotel
Downtown Chicago
Price was ¥264,227, price is now ¥185,062 per person
¥185,062
per person
Nov 13 - Nov 17
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
I loved the location - it was very walkable and lots of restaurants/shops nearby. The room itself was average - beds were very low and the furniture was kind of odd - mostly plywood built ins. But the one room served it's purpose and was clean. The issue was, I had reserved TWO rooms, but when I arrived I was informed they only had one room for me. Apparently they didn't accept the second room reservation... Neither the Emily nor Expedia notified me that one of my "PREPAID" rooms was not reserved. There were NO rooms available in the Hotel for Saturday, nor in the entire city of Chicago on Labor Day weekend, so we were left scrambling to find a place to accomodate the six of us (i.e friends couches, etc.). Not sure which company is ultimately to blame, but needless to say, ALWAYS double check your reservation with this place before you travel.
Reviewed on Sep 3, 2025

The Langham, Chicago
Downtown Chicago
Price was ¥334,268, price is now ¥245,994 per person
¥245,994
per person
Nov 13 - Nov 17
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
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View all trips5* Luxury vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥328,496, price is now ¥222,669 per person
¥222,669
per person
Nov 13 - Nov 17
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep 2, 2025

The Langham, Chicago
Downtown Chicago
Price was ¥334,268, price is now ¥245,994 per person
¥245,994
per person
Nov 13 - Nov 17
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025

Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips3 Night Luxury vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥344,524, price is now ¥295,316 per person
¥295,316
per person
Nov 19 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Overall, the stay was enjoyable. Nice facilities. We really enjoyed the Rooftop restaurant on our first night. Suggestions for improvement include offering a variety of pillow options (preferably down alternatives), a microwave in the room, and vending or self-serve options for water or snacks. My son had to go to a 7-Eleven for water and Gatorade (even though we are club members). The night staff informed me that only one bottle of water was complimentary. I would have gladly paid for one, but that apparently wasn't an option either.
Reviewed on Sep 3, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥428,212, price is now ¥347,528 per person
¥347,528
per person
Nov 19 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep 2, 2025

The Emily Hotel
Downtown Chicago
Price was ¥379,373, price is now ¥318,932 per person
¥318,932
per person
Nov 19 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
I loved the location - it was very walkable and lots of restaurants/shops nearby. The room itself was average - beds were very low and the furniture was kind of odd - mostly plywood built ins. But the one room served it's purpose and was clean. The issue was, I had reserved TWO rooms, but when I arrived I was informed they only had one room for me. Apparently they didn't accept the second room reservation... Neither the Emily nor Expedia notified me that one of my "PREPAID" rooms was not reserved. There were NO rooms available in the Hotel for Saturday, nor in the entire city of Chicago on Labor Day weekend, so we were left scrambling to find a place to accomodate the six of us (i.e friends couches, etc.). Not sure which company is ultimately to blame, but needless to say, ALWAYS double check your reservation with this place before you travel.
Reviewed on Sep 3, 2025
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See all available trips from Tokyo to Far Southeast Side
View all trips4 Night Luxury vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥297,196, price is now ¥184,428 per person
¥184,428
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Overall, the stay was enjoyable. Nice facilities. We really enjoyed the Rooftop restaurant on our first night. Suggestions for improvement include offering a variety of pillow options (preferably down alternatives), a microwave in the room, and vending or self-serve options for water or snacks. My son had to go to a 7-Eleven for water and Gatorade (even though we are club members). The night staff informed me that only one bottle of water was complimentary. I would have gladly paid for one, but that apparently wasn't an option either.
Reviewed on Sep 3, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥328,496, price is now ¥222,669 per person
¥222,669
per person
Nov 13 - Nov 17
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep 2, 2025

The Emily Hotel
Downtown Chicago
Price was ¥279,426, price is now ¥194,844 per person
¥194,844
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
I loved the location - it was very walkable and lots of restaurants/shops nearby. The room itself was average - beds were very low and the furniture was kind of odd - mostly plywood built ins. But the one room served it's purpose and was clean. The issue was, I had reserved TWO rooms, but when I arrived I was informed they only had one room for me. Apparently they didn't accept the second room reservation... Neither the Emily nor Expedia notified me that one of my "PREPAID" rooms was not reserved. There were NO rooms available in the Hotel for Saturday, nor in the entire city of Chicago on Labor Day weekend, so we were left scrambling to find a place to accomodate the six of us (i.e friends couches, etc.). Not sure which company is ultimately to blame, but needless to say, ALWAYS double check your reservation with this place before you travel.
Reviewed on Sep 3, 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.