Central Chicago Romantic Vacations
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Top Romantic vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥268,212
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.
Reviewed on Aug 14, 2026
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View all trips5* Romantic vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
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View all trips3 Night Romantic vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥268,212
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.
Reviewed on Aug 14, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
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.
