
Northwest Side Adults Only Vacations
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Top Adults Only vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.

The Royal Sonesta Chicago River North
Downtown Chicago
Price was ¥334,905, price is now ¥251,736 per person
¥251,736
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone was wonderful and the property and rooms are very well maintained. Will definitely stay there again.
Reviewed on Aug 24, 2025

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ¥487,576, price is now ¥332,861 per person
¥332,861
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!
Reviewed on Aug 18, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥426,754, price is now ¥310,170 per person
¥310,170
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥452,874, price is now ¥335,933 per person
¥335,933
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug 10, 2025

Sentral Michigan Avenue
Downtown Chicago
Price was ¥658,202, price is now ¥501,276 per person
¥501,276
per person
Oct 9 - Oct 14
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (884 reviews)
I liked the location and the views from the aparthotel room that had floor to ceiling corner windows facing the water and the Essex Hotel sign. You could see the sail boats, Grant Park and Shedd Aquarium. The pool area was small and didn’t look as good as the picture.
Reviewed on Aug 22, 2025
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View all trips5* Adults Only vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥426,754, price is now ¥310,170 per person
¥310,170
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥452,874, price is now ¥335,933 per person
¥335,933
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug 10, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥512,076, price is now ¥402,454 per person
¥402,454
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
This is a truly luxurious hotel. I highly recommend it. You can not find a better hotel in Chicago
Reviewed on Aug 20, 2025
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See all available trips from Osaka to Northwest Side
View all trips4 Night Adults Only vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

The Royal Sonesta Chicago River North
Downtown Chicago
Price was ¥334,905, price is now ¥251,736 per person
¥251,736
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone was wonderful and the property and rooms are very well maintained. Will definitely stay there again.
Reviewed on Aug 24, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥426,754, price is now ¥310,170 per person
¥310,170
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥452,874, price is now ¥335,933 per person
¥335,933
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug 10, 2025
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See all available trips from Osaka to Northwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.