West Side Pet-friendly Vacations
Book a Pet-friendly 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 Pet-friendly vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥454,382
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
This was our second stay here this year. Had nice interactions with staff members and a clean room. Will return again!
Reviewed on Sep 1, 2026
5* Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥359,054
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on Sep 1, 2026
3 Night Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
4 Night Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥372,235
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on Sep 1, 2026
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,453
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.
