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 Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥437,434, price is now ￥362,858 per person
￥362,858
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Clean rooms and comfortable beds but the windows were a little thin that you could hear everything outside.
Reviewed on Jun 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥666,224, price is now ￥548,055 per person
￥548,055
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥530,308, price is now ￥441,704 per person
￥441,704
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 2026
Omni Chicago Hotel
Downtown Chicago
Price was ￥452,634, price is now ￥381,384 per person
￥381,384
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
The staff were very helpful and kind, room clean and a beautiful view. Hotel kept up very well. Our air conditioning worked great on the 23rd floor. Check out, bags held and valet parking plus retrieval very quick and excellent service.
Reviewed on Jun 27, 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 ￥498,167, price is now ￥449,412 per person
￥449,412
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Amazing the staff was so friendly. The hotel is just I can’t believe I never stayed at this hotel. This is by far my top five hotels I will definitely be returning. Thank you so much for such a wonderful stay
Kimberly Chardukian
Reviewed on Jun 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥666,224, price is now ￥548,055 per person
￥548,055
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥463,062, price is now ￥457,214 per person
￥457,214
per person
Sep 9 - Sep 13
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
We had a lovely 2 night stay in Chicago and the room with lake view was superb with lovely touches by the cleaning staff who made the stay very special
Reviewed on Jun 1, 2026
3 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 ￥352,949, price is now ￥302,538 per person
￥302,538
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Clean rooms and comfortable beds but the windows were a little thin that you could hear everything outside.
Reviewed on Jun 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥455,368, price is now ￥388,928 per person
￥388,928
per person
Sep 19 - Sep 22
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
4 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 ￥379,384, price is now ￥309,758 per person
￥309,758
per person
Sep 9 - Sep 13
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Perfect location and staff was great!
Reviewed on Jun 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥387,118, price is now ￥320,492 per person
￥320,492
per person
Sep 9 - Sep 13
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,853
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
