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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥586,192
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
I absolutely loved my stay. It was in the perfect location. Walking distance to every site to see. Their customer customer service was great. As well as the in house dining. I definitely will stay here again the next time I visit Chicago
Reviewed on Aug 22, 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
￥488,550
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
First time staying at this
Property and we absolutely loved it! Will definitely go back and recommend
Reviewed on Aug 23, 2026
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View all trips3 Night Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
￥269,536
per person
Sep 26 - Sep 29
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Front desk staff where very unprofessional - friends of theirs hanging out at the desk and when asked for assistance it was as if we were bothering them. housekeeping staff was excellent and attentive when we had to ask for extra bedding and towels since we were 4 not 2pp - these extra items should have been in the room at check in. Pool deck, hot tub, exercise room and sauna/steam area are all top notch. We really loved the concept but would have liked more of a customer service oriented stay.
Reviewed on Aug 23, 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.
