West Side Romantic Vacations
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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 ￥400,778, price is now ￥333,140 per person
￥333,140
per person
Mar 14 - Mar 17
found 21 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥271,808, price is now ￥246,306 per person
￥246,306
per person
Feb 20 - Feb 23
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Very convenient with short walk to the terminal.
Reviewed on Jan 18, 2026
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 ￥170,743, price is now ￥139,374 per person
￥139,374
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥193,946, price is now ￥171,120 per person
￥171,120
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was ￥141,103, price is now ￥141,103 per person
￥141,103
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (748 reviews)
Room was great and spacious. Service was great. The pool and sauna were nice also.
Reviewed on Jan 13, 2026
3 Night Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥271,808, price is now ￥246,306 per person
￥246,306
per person
Feb 20 - Feb 23
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Very convenient with short walk to the terminal.
Reviewed on Jan 18, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥161,242, price is now ￥129,873 per person
￥129,873
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
