West Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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 West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥382,284, price is now ￥325,962 per person
￥325,962
per person
Jan 8 - Jan 11
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥338,470, price is now ￥307,740 per person
￥307,740
per person
Jan 8 - Jan 11
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,141 reviews)
It was okay, nothing terrible, nothing special. The staff was curteous, it waa very convienent.
Reviewed on Oct 31, 2025
5* Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥382,284, price is now ￥325,962 per person
￥325,962
per person
Jan 8 - Jan 11
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
3 Night Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥382,284, price is now ￥325,962 per person
￥325,962
per person
Jan 8 - Jan 11
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
