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.
Level Chicago – Old Town
Downtown Chicago
Price was ￥421,916, price is now ￥309,498 per person
￥309,498
per person
Apr 30 - May 6
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥481,245, price is now ￥312,264 per person
￥312,264
per person
Apr 30 - May 6
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.
Reviewed on Feb 7, 2026
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥579,324, price is now ￥388,004 per person
￥388,004
per person
Apr 30 - May 6
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Pendry Chicago
Downtown Chicago
Price was ￥478,193, price is now ￥332,532 per person
￥332,532
per person
Apr 30 - May 6
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥543,532, price is now ￥396,136 per person
￥396,136
per person
Apr 30 - May 6
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
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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.
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥579,324, price is now ￥388,004 per person
￥388,004
per person
Apr 30 - May 6
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥543,532, price is now ￥396,136 per person
￥396,136
per person
Apr 30 - May 6
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) 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 Osaka 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.
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥387,913, price is now ￥363,420 per person
￥363,420
per person
Apr 5 - Apr 8
found 1 day ago
Roundtrip 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
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Price was ￥347,791, price is now ￥337,560 per person
￥337,560
per person
Apr 5 - Apr 8
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
The people at the admission desk were very helpful.
Reviewed on Jan 15, 2026
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See all available trips from Osaka 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 1 day 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
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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.
