Southern Wisconsin Romantic Vacations
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Top Romantic vacation packages in Southern Wisconsin
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
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Not bad, booked through Expedia back in May for a concert in Late August. We checked in around 5 since our flight got in so late. Even though check in was 3:00pm, our room wasn’t ready. Which was kinda a disappointment, and we didn’t get our room til 7/8pm; However we did get dinner while we waited so that helped. But they accommodated us pretty well and were apologetic. Breakfast was good but didn’t expect it to be “wait to be seated”. But never stood in line very long. Didn’t really use the other “amenities” so kinda thought the extra $89 for these amenities was a tad-bit arbitrary. Maybe I missed that line on Expedia or had booked so long ago I forgot. Either way it was a pretty good location. Lots to eat and do (mostly shop) and see. 15-20 min walk from The Bean.
Reviewed on Aug 31, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥454,382
per person
Oct 1 - Oct 8
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
Hotel could be cleaner. Room was not ready by check in time. Maintenance crew walked into our hotel room while we were there, they didn’t know they had already checked us into the room.
Reviewed on Aug 31, 2026
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View all trips5* Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
￥490,370
per person
Nov 2 - Nov 6
found 13 hours ago
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
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View all trips3 Night Romantic vacations in Southern Wisconsin
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View all trips4 Night Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
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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.
