Northwest Side Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
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Top Adventure vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
￥301,384
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
This hotel was amazing, beds were very comfy and everything was top notch. The only problem I had was valet parking in the description was 83$ but charged me 115.11. But other than that amazing!
Reviewed on Aug 24, 2026
The Peninsula Chicago
Downtown Chicago
￥462,080
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The only negative thing to mention is that the carpeting in the hallways seems quite dated. It needs to be updated.
Reviewed on Aug 24, 2026
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View all trips5* Adventure vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
￥462,080
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The only negative thing to mention is that the carpeting in the hallways seems quite dated. It needs to be updated.
Reviewed on Aug 24, 2026
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See all available trips from Tokyo to Northwest Side
View all trips3 Night Adventure vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
￥269,536
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,055 reviews)
Front desk staff where very unprofessional - friends of theirs hanging out at the desk and when asked for assistance it was as if we were bothering them. housekeeping staff was excellent and attentive when we had to ask for extra bedding and towels since we were 4 not 2pp - these extra items should have been in the room at check in. Pool deck, hot tub, exercise room and sauna/steam area are all top notch. We really loved the concept but would have liked more of a customer service oriented stay.
Reviewed on Aug 23, 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.
