Central Chicago Adults Only Vacations
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Top Adults Only vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥238,023, price is now ￥192,498 per person
￥192,498
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all
Reviewed on Feb 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥286,713, price is now ￥240,126 per person
￥240,126
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Pendry Chicago
Downtown Chicago
Price was ￥235,598, price is now ￥198,214 per person
￥198,214
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥301,802, price is now ￥255,608 per person
￥255,608
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
The Emily Hotel
Downtown Chicago
Price was ￥241,574, price is now ￥208,057 per person
￥208,057
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.
Reviewed on Jan 25, 2026
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View all trips5* Adults Only vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥286,713, price is now ￥240,126 per person
￥240,126
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥301,802, price is now ￥255,608 per person
￥255,608
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥271,656, price is now ￥261,632 per person
￥261,632
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Room was great and staff very attebtive and kind
Reviewed on Jan 20, 2026
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View all trips3 Night Adults Only vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥238,023, price is now ￥192,498 per person
￥192,498
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all
Reviewed on Feb 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥286,713, price is now ￥240,126 per person
￥240,126
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Pendry Chicago
Downtown Chicago
Price was ￥235,598, price is now ￥198,214 per person
￥198,214
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips4 Night Adults Only vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥289,464, price is now ￥250,835 per person
￥250,835
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Staff was amazing throughout our stay. Room very clean, property well maintained. Great location
Reviewed on Feb 1, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥321,010, price is now ￥254,210 per person
￥254,210
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all
Reviewed on Feb 2, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥287,616, price is now ￥251,324 per person
￥251,324
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Friendly staff, accommodating- we arrived earlier than our check-in time and they were able to get us in our room promptly.
Reviewed on Feb 3, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
