Central Chicago Adventure Vacations
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Top Adventure vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
￥425,405
per person
Nov 5 - Nov 9
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
The Talbott, Autograph Collection
Downtown Chicago
￥322,514
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
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View all trips5* Adventure vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
￥425,405
per person
Nov 5 - Nov 9
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
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See all available trips from Tokyo to Central Chicago
View all trips3 Night Adventure vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips4 Night Adventure vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
￥425,405
per person
Nov 5 - Nov 9
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
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See all available trips from Tokyo to Central Chicago
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
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.
