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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥374,696, price is now ￥314,217 per person
￥314,217
per person
Jun 11 - Jun 14
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Staff were awesome!! Room view was amazing . Only complaint if I had one would be we didn’t get our room turned over one of the days.
Reviewed on Mar 28, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥546,288, price is now ￥399,292 per person
￥399,292
per person
Apr 29 - May 5
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
This is the best hotel I’ve been so far, their staffs were supper nice and their rooms are amazing, thanks
Reviewed on Mar 28, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥437,268, price is now ￥349,207 per person
￥349,207
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥641,108, price is now ￥516,587 per person
￥516,587
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
5* Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥641,108, price is now ￥516,587 per person
￥516,587
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 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 ￥294,630, price is now ￥250,159 per person
￥250,159
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Refused to park my challenger for valet
Reviewed on Mar 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥434,357, price is now ￥350,134 per person
￥350,134
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Elegant and beautiful
Reviewed on Mar 26, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥374,696, price is now ￥314,217 per person
￥314,217
per person
Jun 11 - Jun 14
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Staff were awesome!! Room view was amazing . Only complaint if I had one would be we didn’t get our room turned over one of the days.
Reviewed on Mar 28, 2026
4 Night Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥368,508, price is now ￥321,763 per person
￥321,763
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥444,579, price is now ￥347,496 per person
￥347,496
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
This is the best hotel I’ve been so far, their staffs were supper nice and their rooms are amazing, thanks
Reviewed on Mar 28, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
