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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥244,466, price is now ￥205,382 per person
￥205,382
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The check in staff was perfect the room spotless and my arrival was flawless.
Reviewed on Jan 18, 2026
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 17 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
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥282,630, price is now ￥243,250 per person
￥243,250
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026
The Emily Hotel
Downtown Chicago
Price was ￥335,613, price is now ￥299,958 per person
￥299,958
per person
Mar 14 - Mar 17
found 17 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Nice newer hotel with lots of options. Rooms are a bit industrial but fine, nothing super luxurious but adequate.
Reviewed on Jan 16, 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 ￥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
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 17 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
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥282,630, price is now ￥243,250 per person
￥243,250
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026
3 Night Romantic vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥143,466, price is now ￥100,180 per person
￥100,180
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The check in staff was perfect the room spotless and my arrival was flawless.
Reviewed on Jan 18, 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 12 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.
