Southern Wisconsin 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 Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
￥427,084
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
Impeccable hotel! Room was clean. Staff were helpful and kind. Location is perfect. Good food and bar in hotel.
Reviewed on Aug 30, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips5* Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
￥1,104,403
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Tokyo (HND) 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
Don't see what you're looking for?
See all available trips from Osaka to Southern Wisconsin
View all trips3 Night Romantic vacations in Southern Wisconsin
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 Southern Wisconsin
View all trips4 Night Romantic vacations 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
￥353,818
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
Let me first start with the view, the view was absolutely gorgeous. Downtown Chicago skyline is stunning from the pier. Did I mention the windows are floor to ceiling!? Lovely!! We stayed on the 7th floor, The view indeed was my favorite part. Now there are plenty of restaurants and places to eat or snack on the main floor I suggest you bring your walking shoes as there will be a lot of walking required to get up to your room. I told the lady at the front desk you guys need a scooter to get us to the tiers lol. The hotel is beautiful if you’re driving, I suggest using valet, it’s cheaper than the parking garages . $76 per night for valet was worth it because we left out a lot. Staff was great, friendly and answered all questions and very informative. I would definitely be returning and I would definitely recommend.
Reviewed on Sep 2, 2026
Don't see what you're looking for?
See all available trips from Osaka to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
