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 Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥113,774, price is now ￥89,698 per person
￥89,698
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
8.4/10 Very Good! (2,079 reviews)
Room was really small and bathroom was smaller. The sink was like 12”x12”.
Reviewed on Aug 1, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥179,800, price is now ￥138,332 per person
￥138,332
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9.6/10 Exceptional! (1,945 reviews)
Everything was perfect. Room, bar, staff, pool, gym, spa.
Reviewed on Aug 1, 2026
Level Chicago - River North
Downtown Chicago
Price was ￥128,225, price is now ￥100,296 per person
￥100,296
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities
Reviewed on Jul 30, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥111,668, price is now ￥90,778 per person
￥90,778
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9/10 Wonderful! (3,732 reviews)
Great location, clean and beautiful. Elevator from ground to level floor was out several nights and the rooftop was not open.
Reviewed on Aug 1, 2026
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View all trips5* Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥179,800, price is now ￥138,332 per person
￥138,332
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9.6/10 Exceptional! (1,945 reviews)
Everything was perfect. Room, bar, staff, pool, gym, spa.
Reviewed on Aug 1, 2026
Don't see what you're looking for?
See all available trips from Washington 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.
