Far Southeast Side Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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 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 ￥317,844, price is now ￥260,780 per person
￥260,780
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was friendly, and room was cleaned well. Free breakfast was also a nice touch and better than expected
Reviewed on Feb 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥327,736, price is now ￥273,442 per person
￥273,442
per person
Mar 8 - Mar 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Pendry Chicago
Downtown Chicago
Price was ￥324,568, price is now ￥280,430 per person
￥280,430
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥329,728, price is now ￥286,210 per person
￥286,210
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.
Reviewed on Feb 2, 2026
The Emily Hotel
Downtown Chicago
Price was ￥302,738, price is now ￥268,348 per person
￥268,348
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.
Reviewed on Jan 25, 2026
Don't see what you're looking for?
See all available trips from Osaka to Far Southeast Side
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 ￥327,736, price is now ￥273,442 per person
￥273,442
per person
Mar 8 - Mar 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
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 ￥263,141, price is now ￥228,504 per person
￥228,504
per person
Mar 8 - Mar 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was friendly, and room was cleaned well. Free breakfast was also a nice touch and better than expected
Reviewed on Feb 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥327,736, price is now ￥273,442 per person
￥273,442
per person
Mar 8 - Mar 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Don't see what you're looking for?
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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥282,532, price is now ￥255,479 per person
￥255,479
per person
Apr 2 - Apr 6
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Service was amazing and the location was perfect. Would definitely stay here again.
Reviewed on Jan 28, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
