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.
Hotel Riu Plaza Chicago
Downtown Chicago
￥442,502
per person
Sep 20 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.
Reviewed on Aug 20, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
￥464,727
per person
Sep 20 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
We absolutely loved it here. You have to get the river view! Property is clean and staff is so hopeful a nice! Worth every dollar spent!
Reviewed on Aug 20, 2026
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View all trips5* Adventure vacations in Central Chicago
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View all trips3 Night Adventure vacations in Central Chicago
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View all trips4 Night Adventure vacations in Central Chicago
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Hotel Riu Plaza Chicago
Downtown Chicago
￥270,684
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.
Reviewed on Aug 20, 2026
Four Seasons Hotel Chicago
Downtown Chicago
￥425,405
per person
Nov 5 - Nov 9
found 1 day 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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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.
