Northwest Side Cheap Vacations
Book a Cheap Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Cheap vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥268,212
per person
Sep 26 - Sep 29
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.
Reviewed on Aug 14, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips5* Cheap vacations in Northwest Side
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 Northwest Side
View all trips3 Night Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥268,212
per person
Sep 26 - Sep 29
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.
Reviewed on Aug 14, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
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.
