West Side Romantic Vacations
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- 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
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Top Romantic vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
Price was ￥423,084, price is now ￥346,048 per person
￥346,048
per person
May 11 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,811 reviews)
Food wasn’t that great from the bar
Reviewed on Mar 7, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥482,023, price is now ￥379,285 per person
￥379,285
per person
May 12 - May 16
found 20 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.
Reviewed on Mar 3, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥436,346, price is now ￥364,118 per person
￥364,118
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Izumo (IZO) to Chicago (ORD)
8.8/10 Excellent! (2,060 reviews)
Good place but a bit expensive for rooftop ambiance.
Reviewed on Mar 3, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥439,550, price is now ￥367,340 per person
￥367,340
per person
May 11 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
We chose this hotel for my husband’s birthday weekend. The room was spacious clean and trendy. The bed was so comfortable. The happy hour was excellent and the game room and bar on the second floor was fabulous. The customer service was phenomenal. They surprised my husband with a goody bag for his birthday which was the icing on the cake. The hotel is currently undergoing renovations but it was still a great stay.
Reviewed on Mar 3, 2026
5* Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥415,862, price is now ￥373,352 per person
￥373,352
per person
May 1 - May 4
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
The spa was relaxing and the staff was so kind.
Reviewed on Mar 7, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥482,023, price is now ￥379,285 per person
￥379,285
per person
May 12 - May 16
found 20 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.
Reviewed on Mar 3, 2026
3 Night Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥306,754, price is now ￥255,538 per person
￥255,538
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,060 reviews)
Good place but a bit expensive for rooftop ambiance.
Reviewed on Mar 3, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥371,797, price is now ￥317,530 per person
￥317,530
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.
Reviewed on Mar 3, 2026
4 Night Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥436,346, price is now ￥364,118 per person
￥364,118
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Izumo (IZO) to Chicago (ORD)
8.8/10 Excellent! (2,060 reviews)
Good place but a bit expensive for rooftop ambiance.
Reviewed on Mar 3, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥482,023, price is now ￥379,285 per person
￥379,285
per person
May 12 - May 16
found 20 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.
Reviewed on Mar 3, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
