
Far Southeast Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥109,000 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 Romantic vacation packages in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago
Downtown Chicago
Price was ¥383,936, price is now ¥332,626 per person
¥332,626
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Great location. Rooms are spacious and staff is amazing!! I would highly recommend!!!
Reviewed on Nov 12, 2026


Eurostars Magnificent Mile
Downtown Chicago
Price was ¥427,255, price is now ¥353,562 per person
¥353,562
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)
Very clean, modern rooms, great view, helpful staff. WIll stay here again when i visit Chicgao next
Reviewed on Nov 12, 2026

Pendry Chicago
Downtown Chicago
Price was ¥449,685, price is now ¥374,363 per person
¥374,363
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all tripsThings to do

Skydeck Chicago at Willis Tower
¥6,636
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.


