South Side Mountain Vacations
Book a Mountain 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
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Top Mountain vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥378,182
per person
Nov 9 - Nov 13
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on Oct 7, 2026
5* Mountain vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥378,182
per person
Nov 9 - Nov 13
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on Oct 7, 2026
4 Night Mountain vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥378,182
per person
Nov 9 - Nov 13
found 4 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on Oct 7, 2026
Things to do
Skydeck Chicago at Willis Tower
￥6,642
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.
