Far Southeast Side Romantic Vacations
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Top Romantic vacation packages in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥492,738
per person
Oct 1 - Oct 8
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Loved it and definitely feel like the bathroom was made for the girls! Just wish we had gotten a response for requests we madr but other than that it was a good hotel! Loved the breakfast.
Reviewed on Aug 31, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥454,382
per person
Oct 1 - Oct 8
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
I’ve stayed at several hotels in this area and the Silversmith is by far the nicest. The hotel staff were very friendly and accommodating. The room was clean, comfortable and quiet. Highly recommend!
Reviewed on Aug 31, 2026
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See all available trips from Tokyo to Far Southeast Side
View all trips5* Romantic vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
￥490,370
per person
Nov 2 - Nov 6
just found
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
Four Seasons Hotel Chicago
Downtown Chicago
￥383,555
per person
Oct 3 - Oct 6
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable
Reviewed on Aug 30, 2026
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See all available trips from Osaka to Far Southeast Side
View all trips3 Night Romantic vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips4 Night Romantic vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
￥490,370
per person
Nov 2 - Nov 6
just found
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
Don't see what you're looking for?
See all available trips from Osaka to Far Southeast Side
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
