Far Southwest Side Romantic Vacations
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Top Romantic vacation packages in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥437,691, price is now ￥317,486 per person
￥317,486
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.
Reviewed on Aug 23, 2025
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥487,576, price is now ￥332,861 per person
￥332,861
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!
Reviewed on Aug 18, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥619,739, price is now ￥445,722 per person
￥445,722
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥447,267, price is now ￥324,048 per person
￥324,048
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location
Reviewed on Aug 22, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥458,348, price is now ￥333,252 per person
￥333,252
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
I give this hotel five stars. A very clean atmosphere. The staff is amazing, the valet workers knew my name, but the best was when I opened that door and seen that window view. It was amazing, gorgeous absolutely beautiful!! I would definitely stay again and tell people what a great experience I had here!
Reviewed on Aug 24, 2025
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View all trips5* Romantic vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥619,739, price is now ￥445,722 per person
￥445,722
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥620,255, price is now ￥467,278 per person
￥467,278
per person
Oct 9 - Oct 14
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
This is a truly luxurious hotel. I highly recommend it. You can not find a better hotel in Chicago
Reviewed on Aug 20, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥540,511, price is now ￥465,787 per person
￥465,787
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Beautiful, updated property with modern elegance situated in the heart of Chicago with access to literally everything. Will definitely be returning!
Reviewed on Aug 23, 2025
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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.